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Rebound
By Pamela
The phone call came at noon time on a Saturday in the beginning of August. My Grandma Ida, who lives a thousand miles away from us in South Florida, had taken a nasty tumble. My parents booked seats on the last flight of the day to Miami and were running around the house like chickens with their heads cut off packing and otherwise getting ready to go. My mom was convinced that Grandma was now going to have to sell her house and move into an assisted living facility. Mom and Dad would have to spend a week or more getting her house ready to sell and moving Grandma’s stuff to a new apartment.
My dad told me to pack a suitcase. “We can’t have you staying here alone while we’re gone for two weeks.”
“But dad, I’ll be a high school senior in a few weeks. I’m old enough to take care of myself.”
“No, Greg,” my dad said. “We’re going to lock up the house tight with the alarm turned on. We’re trying to figure out where you can stay.”
I guess I was lucky that they weren’t going to force me to go with them. As much as I love my grandma, I’m enrolled in a summertime NSF mathematics course at the local university that I’ve got to complete. Getting the math course on my resume could make all the difference in getting into MIT – my college of first choice.
As they run around the house my parents brainstorm possible nearby relatives who could take me in. None are available so finally they call our neighbors next door, the Twillers.
Our two families have been great friends since even before I was born. I played with the Twillers daughter Bonnie, who’s two years older than me, up until she went through puberty and blossomed into a super cool, voluptuous, and pretty young woman. She and I no longer hang out since she has endless boyfriends hovering around her. Besides that I’ve never figured out how to be cool.
My dad said, “Bonnie is next door this summer – back from her freshman year at college. She’s alone there since her folks are on a canoe trip at Hudson’s Bay. You’ll be happy to know that she’s more than happy to have you stay there.”
This news is a bit surprising since I can’t believe I won’t be a liability for her social life. How could her somewhat dorky, young, next door neighbor boy not interfere in all the cool things she’s planning while her parents are away? I’m not totally dorky, but I’m two years behind her in school which is an enormous gap at our age. I also happen to look younger than I am. Puberty for me – besides all the usual physical stuff like acne and pubic hair showing up – was the permanent addition of a massive hunger for girls added to my love of mathematics.
The equations in my head are now accompanied by images of girls and their body parts. I don’t present to women with a strong, muscular body, or handsome, masculine face. I’m not bad looking but there’s a touch of softness to my face almost like I am somewhere in the zone between male and female. My small-boned frame fits in with this picture as well – a body that isn’t quite masculine nor exactly feminine.
I asked my dad, “Bonnie’s more responsible than I am?”
“Of course. She’s a college student.”
“If you say so.”
“I do say so. She’s a levelheaded, conscientious young lady. Anyway, in ten minutes our Uber is coming to take your mom and me to the airport. Are you done packing your suitcase?”
“No.”
“Hurry up then. Pack everything you’ll need for at least a week or two. Hurry!”
I threw my clothes into my suitcase in a great rush. I gathered up my math books and my computer and put them into the suitcase. I got my toothbrush and was scouting around looking to see what else I might need when my dad yelled. “C’mon Greg. That’s it. Our ride is here and I have to turn the alarm on and lock up the house.”
I ran outside carrying my suitcase where my mom kissed me goodbye. “Run on over to the Twillers and ring the bell. I want to make sure Bonnie is there to greet you.”
I said goodbye to my dad and walked across the yards to the front door of the Twillers house and rang the bell. Bonnie came out and she and I waved to my parents as they got into the Uber.
***
“Welcome, Greg,” Bonnie said laughing.
“What’s so funny?” I asked.
“Just that I suddenly have been appointed your guardian. You’re my little charge for a week or longer. I never would have anticipated such an occasion.”
“I have to obey you?” I asked.
“I’m afraid so, Greg. Your dad said that’s not a problem for you.”
“No, I guess not. The last thing I want to do is make your life complicated by not obeying you. I’ve always liked playing with you when we were young. Eventually I became too young for you to be with.”
“I hope I never hurt your feelings.”
“No. You sort of went from a girl let’s say to a … you know, a woman. I see you as a woman, not the girl you used to be.”
Bonnie laughed. “You’re so cute Greg. I’m not sure if I see you as a boy or a man. Probably because I don’t know you very well anymore.”
“I don’t want my presence to be a pain for you Bonnie. So if you need to just keep me locked up somewhere so I can’t bother you than go ahead and do it.”
“Shame on you Greg. You’re not going to be a pain. Let me show you to the guest bedroom.”
***
I can count on one hand the number of dates I’ve had with girls. Sad, very sad! As my desire for girls exploded after puberty my fevered brain found only one possible outlet to satisfy my cravings for the opposite sex: Investigate my mom’s clothing. I haven’t worn any of her clothes. That’s too scary. No. I’ve gone through her drawers and closet examining her clothes. I’ve inspected all her bras and panties, one by one. I’ve even given them names. Like ‘Susie’ is her one pink bra. ‘Joan’ is her black lace bra. Her white bras are, ‘Annie1’, Annie2’ all the way up to ‘Annie5’. For some crazy reason I’ve given my mom’s panties boys names. Like ‘Ralph’ is her silky panty with pink flowers on it.
My mom seems to love girdles and those I give royal names like ‘Queen Elizabeth,’ or ‘Princess Isabella,’ for the two prettiest ones she owns. Her white slips I’ve called ‘Ms. Julie1,’ ‘Ms. Julie2,’ and so forth. You get the picture: I’m really weird but this is what a mathematician like me does when confronted with the tremendous disorder of a lingerie drawer. How else to make sense of all these glorious, sexy clothes that spur endless erotic fantasies in my mind.
I’ve also carefully studied my mom’s skirts, dresses, blouses, and shoes. I’ve given them the names of famous mathematicians, physicists, and Noble Prize recipients. My mom’s prettiest dress – or at least the one I am most in love with – is pink and fluffy and I’ve christened that dress as Carl Friedrich Gauss. I’m sure you don’t want to hear the names I’ve given to all mom’s dresses and shoes.
The most ridiculous thing I’ve done is investigate the daily changes in my mom’s clothing hamper to see what order she wears her bras and panties each week. I mean it could be ‘Annie3’, ‘Joan’, then ‘Annie 2’ for the bras and ‘Ralph’, ‘George’, ‘Henry’ and so on for the panties. Weird, right?
I think I’ve embarrassed myself enough by demonstrating how exhaustively I’ve studied my mom’s clothes. Of course Bonnie has no idea about my infatuation with women’s clothing. Now that I’ll be staying in her house the thought has passed through my mind that both Bonnie and her mom’s clothing are sitting in their bedrooms waiting for me to examine. But I mustn’t touch their clothes. All I need is for Bonnie to figure out I’m going through her clothes or her mom’s clothes. She’ll kick me out and rightly so!
***
You can’t imagine how much Bonnie Twiller has been a part of my sex fantasies. She’s gorgeous. Every aspect of her excites me. Her pretty face, her prominent breasts, the lovely curve of her rear end and her slim waist. Her pretty polished finger and toenails. Her light brown hair is a wondrous beauty cascading down her shoulders to her back.
After she showed me to my room she said, “Make yourself at home, Greg. Do you like to swim? The pool is great!”
I used to swim all the time in the Twiller’s pool when Bonnie and I played together. I had always loved seeing her in a bathing suit. But it was only after I went through puberty did I realized why I loved looking at her.
“I’d love to swim in the pool,” I said.
“Good, feel free!”
She left me alone and as I went to put my clothes into the dresser I realized that I had forgotten my bathing suit. Not knowing what I should do, I told Bonnie the news. “I guess I’ll just sit next to the pool, unless maybe your dad has a suit I could borrow.”
“Don’t be silly Greg,” Bonnie said. “My dad’s bathing suit can hold two of you. But, actually, I’ve got an old bathing suit that you can wear. I think it’ll fit you.”
“It’s a girls’ bathing suit?”
“Yes. Oh, I see, you’re embarrassed to wear it?”
“Shouldn’t I be?”
“I don’t know, Greg. The pool is private. No one will see you and I don’t care at all.”
“Well …”
“I’ll get it and you can decide what you want to do.”
Bonnie looked through the bottom drawer of her dresser and found a pink one-piece bathing suit that she handed to me.
“It’s pink,” I said.
“Yes. I went through a pink phase a few years ago.”
I held up the suit and looked at it closely, “My mom has the identical suit, though hers is blue.” I studied the label and said, “Exactly the same company.”
“Greg, when would you have studied your mom’s bathing suit so closely? I mean how many boys would know what brand their mom’s bathing suit is?”
“I guess I’m really strange, but you see, one day I overheard my mom talking to the ladies in her bridge group about how girls can buy bathing suits based on their bra size, as against just you know small, medium, and large.”
“That’s the conversation you listened to?”
“I just happened to be there in the next room. Anyway it made me wonder about what kind of bathing suit my mom had.”
“Why?”
“I’m not exactly sure. It might be that I’m really interested in math and I was wondering how bathing suits can be made that take into account a bunch of different geometric sizes.”
“Okay. What did you find out?”
“I sort of got mesmerized by the complexity of the bathing suit itself. How people could figure out a shape that matched the shape of women’s bodies. First of all there’s the lower part that has to contain a woman’s or girl’s … you know … her tush.” I held up the pink bathing suit and pointed to the lower panty part. “It’s really amazing that it is the right shape for a woman.”
“I know it’s incredible,” Bonnie said sarcastically. “Go on, Greg.”
“See how your bathing suit has – this kind of extra fabric in the crotch area. That’s interesting. I’m not too sure why they make it like that.”
“It’s called the gusset,” Bonnie said. “It reinforces the material and the stitching. It’s an area of the bathing suit that gets a lot of wear and tear.”
“Good to know. The top part has straps to hold it up and where the bosoms go …”
“Bosoms, I love that. Go on.”
“That’s not what they are?”
“They’re bosoms but most boys would call them boobs, or tits, or even breasts. Bosoms is a bit formal and old fashioned.”
“I’m sorry.”
“No need to apologize.”
“Well, in the place where the girl puts her boobs they have these kinds of support things.” I pointed to them in Bonnie’s bathing suit.
“It’s a liner to help hold a girl’s breasts more snugly and give her a better shape in the bathing suit.”
“That’s all so interesting. Your bathing suit is a 36B. My mom’s is a 38C.”
“You know about bra sizes?”
“Yeah. I studied that a bit. You’re not still 36B are you?”
Bonnie laughed. “That suit is from years ago. Now I’m 36D. The girls in my family are either D or DD. My mom is DD. I can’t believe I’m having this conversation with you.”
“I guess I’m really weird,” I said.
“Don’t worry about it Greg. I can understand boys being interested in the size of girls breasts. Are there any other sizes that you’ve studied for girls’ clothing?”
“I know this is bizarre, but after studying my mom’s bathing suit I was curious to look at her bras, I mean to see if they also were 38C. I checked them out and they were.”
“You checked every bra?”
“Well I was curious about them and each one is different than the other and they’re different colors, except white is the most common color.”
“So you opened up your mom’s lingerie drawer and went through all her bras. What did you notice about them besides the size?”
“I looked at the lace, at the straps which are different widths, at the little bows. Some have two hooks in the back and some have three. I noticed that the cups can have no seams or several seams.”
“And that’s all you studied?”
“My mom’s panties are in the drawer next to her bras, so I was also curious about them. They’re really interesting. So many colors, some even have flowers on them. Some cover more of her than others. There was even a thong which I figured out from looking it up on the internet.”
“Bras, panties, bathing suit. Is there more?”
“Yes, I’ve looked at all her clothing. Everything she owns. Her dresses, skirts, blouses, shoes, purses. It’s all so fascinating. I’ve really enjoyed it, oh, and what I especially loved looking at were her girdles. She’s got like eight of them. Some are super pretty and some seem kind of plain looking. I must admit that they’re an amazing engineering feat – assuming they work.”
“Work?”
“I read that they’re supposed to create a shape that women like. Is that true?”
“Why, yes, Greg. Girdles do help girls get the figure they want.”
“Do you wear girdles?”
“Yes, I have a few.”
I looked at Bonnie waiting for her to explain why she wore them. When she didn’t say anything I said,” But why would you wear a girdle. I think your figure is perfect!”
“That’s sweet of you Greg. I’ve needed my girdles when I’ve been a bridesmaid wearing tight dresses. It’s good to get one’s shape held down while the dress reveals my curves in such detail. Is there anything else about this … obsession of yours?”
“Just that I’ve named all my mom’s clothing.”
“Named it?”
“Given them names.”
“What’s that mean?”
“For example, Susie is her pink bra. I use Annie1, Annie2 and so forth for her white bras …”
“You’ve named her dresses and girdles?”
“Sure. All her clothes.”
Bonnie shook her head in wonderment. “So there’s not one article of your mom’s clothing that you haven’t inspected?”
“Yeah.”
“She never got suspicious that you’re looking at her clothes?”
“Not that I’m aware.”
“Have you worn any of her clothes?”
“No!”
“But you want to?”
“I think it’s wrong to wear someone else's clothes without their permission. I know it might be wrong to inspect someone else’s clothes, but to me it’s halfway between not touching them and wearing them. I can’t not touch them – I mean I’m too weak to stop myself from looking at women’s clothing, but not so weak that I can’t draw the line against wearing them.”
“What does it mean that you’re too weak not to examine your mom’s clothing? What’s that all about?”
“I haven’t been able to get a girlfriend but I so love girls. I’m very shy which could be my problem. My mom’s clothing allows me to at least experience something to do with girls. That’s what I mean.”
“Shyness could surely be a factor, but I’m wondering if you’re hurting your chances of getting a girlfriend by being preoccupied with girl’s clothing. How to put this delicately, but girls generally are happy for the girl stuff to be the preoccupation of girls and the boy stuff the kind of things that boys are into.”
“You mean they sense that I’m too much interested in girl’s clothing so they don’t see me as being a boyfriend?”
“I’m afraid so, but I’m definitely not telling you to not have an interest in girl’s clothing. You like girl’s clothing so go ahead and enjoy it! I bet that there are some girls that prefer boys like that. There might even be boys that prefer boys that like girl’s clothing and pretend that they’re girls!”
“You know so much, Bonnie, and I have so much to learn.”
“I take from all of this that if you had the chance you’d wear girl’s clothing.”
“I guess so.”
“So my bathing suit is your very first chance to dress in girl’s clothing?”
“Yes.”
“So go ahead, Greg. Knock yourself out!”
Bonnie looked at her watch and said, “I’ve got to meet a couple of my girlfriends and I’ll be back before dinner. Are you thinking of looking at my clothes or my mom’s clothes while I’m gone?”
“I’ve thought of the fact that you and your mom have all these clothes that I’d be curious to see, but I swear I completely nixed the idea that while I’m a guest here I would ever sneak around in your private bedrooms.”
Bonnie laughed, “I appreciate you being honest and I believe you, Greg. Tomorrow I’ll be away most of the day. It’s okay with me if you straighten out my clothes. My lingerie drawer is a mess of panties and bras. My stockings are all screwed up. I hate to think of my closet. Would you be willing to do that?”
“Oh, my God, Bonnie. I would love to do that!”
“I won’t mind then if you play your halfway game with my clothes while you straighten them out.”
“I can’t thank you enough.”
“In the meantime, I want you to wear my old bathing suit and have a nice swim. You’re a good swimmer aren’t you? You don’t need a lifeguard?”
“I won’t need a lifeguard. Wow, wearing your bathing suit. I can’t believe I’m finally going to …”
“Pretend that you’re a girl?”
“Yeah, I guess that’s what I was thinking.”
Bonnie left and I sat down on the edge of my bed holding her bathing suit. My heart was pounding; I had a rising feeling of excitement like I had felt as a kid on the few times my parents allowed me to do something I really wanted to do. A fishing trip one time, a ride on the Cyclone at Coney Island another time. In each case a powerful feeling of happiness even giddiness came to me and that’s how I felt now. I’m going to put on this pretty pink girl’s bathing suit and all of a sudden for the very first time I’ll look and feel like a real girl.
I took off my clothes. I trembled putting one foot and then the other through the leg opening and then I slowly pulled it up my legs. The material had some flexibility to it and conformed to the shape of my buttocks. The thought came to my mind that undoubtedly the bathing suit that was now enclosing my penis had often times been closely containing Bonnie’s vagina and pubic hair. Evidently my penis was listening in on this thought since it jumped up into a boner as the suit went on. I got the suit past my hips and put my arms into the straps and made some adjustments. The room allocated for the bust was more than my flat chest needed, but the cups stood out on their own creating the illusion that I had small breasts.
I tucked my boner down as best I could and found a mirror. Oh my God, I thought looking at my image. Wow! There was so much girl in the mirror looking back at me. An eruption of feminine feelings filled my mind. I flitted about the room in an exaggerated imitation of a ballerina. I was finally liberated from my male self – at least for this wonderful afternoon. I could spread my wings as a girl!
I took a large pink towel that had been in the bathroom and went downstairs and out the back door to the pool. I spread the towel on a chaise lounge and walked over to the water and stuck my toe in. All my movements and gestures were as girl-like as I could conjure up.
The water wasn’t cold and I jumped in the water as I had seen many girls jump and swam a bit to cool off. There was a chair-like float with cup holders. I went back inside the house to the kitchen, poured myself a ginger ale, and took it back to the pool. I climbed onto the float and allowed myself to float aimlessly sipping my drink and feeling on top of the world.
Eventually my boner subsided and I tucked my member backwards and gazed at the lovely sight of myself in the pink bathing suit. I felt as happy as I had the day I found a proof for a particularly irksome theorem that my high school math teacher had challenged the class with. That day I’d felt good about myself for being clever, but in this moment in the pretty bathing suit feeling deliciously feminine, I had to say this was an even better experience. Was I nuts?
When my drink was gone I slipped back into the water and then lay down on a chaise lounge underneath an umbrella. I closed my eyes and dozed off. I’m not sure how long I was sleeping when I was awakened by the sound of talking. It was Bonnie and a couple of her girlfriends dressed in bikinis and holding towels.
“Hi Greg,” Bonnie said smiling. “Meet Jill and Maive.”
“Hi,” I said wondering if I should cover myself up with the towel. Jill and Maive were as gorgeous as Bonnie. The three women had no shortage of erotic curves as accentuated in their skimpy bathing suits.
“You look cute in the bathing suit,” Bonnie said and turning to her friends added, “He forgot to bring his suit so I loaned him my old one.”
“Don’t be shy,” Maive said. “Stand up and let’s see you.”
When I stood up she motioned with her fingers for me to twirl around so she could see me from all sides. I rotated around as gracefully as I could figure.
“Doesn’t he look cute in that,” Maive said. “It fits him so perfectly.”
“If he had some boobs he’d look exactly like a young girl,” Jill said. “You’re pretty Greg.”
Maive laughed. “I’m sure he doesn’t want to hear that Jill. Do you Greg?”
“Am I really pretty?” I asked.
The girls laughed.
“For sure,” Jill said. “You make a pretty girl in that bathing suit.”
I didn’t know what to say and Bonnie said, “Greg, I told Maive and Jill about your halfway obsession. They agree with me that it’s okay if you want to pretend you’re a girl. None of us are judgmental.”
“Thank you,” I said.
The girls picked out three chaise lounges next to mine, put down their towels and one by one dived into the pool. I couldn’t pull my eyes away from watching them frolicking in the water. The sight of girls being girls was mesmerizing. I felt my boner returning and tried to look away without success.
A short while later the girls climbed out of the pool and lay down on the chairs next to me.
“When did the boys say they’re coming?” I overheard Jill asking her friends.
“Around six,” Maive said.
Boys? Uh, oh. “Boys are coming, Bonnie?” I asked.
“Yeah. My summer boyfriend, Tom, Jill’s fiancé Dick, and Maive’s boyfriend Harry. They’ll be here for dinner, a swim, and hopefully a movie.”
The girls laughed. “What’s funny?” I asked.
“Movie is a euphonism for making out,” Jill said. “The boys will give us no choice but to have to kiss them!”
“I guess I can watch the movie for all of you and tell you what it’s about,” I said.
“Really?” Maivie said, “Oh my God Bonnie he’s teasing us!”
“When you swim the boys shouldn’t see me in your bathing suit, should they?”
“Why not? They’re nice boys. They’ll understand that you forgot your bathing suit,” Bonnie said.
“Right.” I wondered if Bonnie was being optimistic. Perhaps college age kids are nicer than high school kids.
At about five o’clock the girls got up to wash off and change and get ready for their dates. I went to my room, where I discovered to my chagrin that I had also forgotten to bring underwear. I knocked on the open door to Bonnie’s room without looking in.
“Come in Greg,” she said.
I walked in just as the three girls were in the final stages of putting on their shorts and tops. I saw different amounts of their panties and bras until they were safely hidden within their outer clothes.
“I’m terribly sorry, Bonnie, I feel like such a dunce, but I forgot to bring my underpants with me. Maybe I could wear your dad’s?”
Bonnie laughed. “No, his clothing will never fit you.”
“I guess I can go commando …”
Bonnie laughed again, “No need, Greg. I’ll give you one of my old panties to wear. It’s no longer in my rotation.”
From the back of her panty drawer Bonnie found a pink panty and pulled it out.
“It’s full coverage and high waist so it should be fine for your you know what.”
“My you know what?” I asked.
Maive and Jill laughed. “Greg,” Jill said, “you’re obviously enjoying yourself,” and pointed at the lower part of my bathing suit where there was evidence of my boner struggling against the fabric.
“I’m sorry!”
“Relax, Greg. That’s one thing girls know all about,” Bonnie said.
“If Bonnie gave you bikini cut panties your wiener might fall out!” Maive said. “These panties will keep it where it belongs!”
“You’re talking about my … thing falling out?” I said.
“Don’t listen to them, they’re being silly. These are nice comfortable panties. Enjoy them!”
“Okay.”
“We’ll be having pizza tonight at about 6:30. You should join us. I’ll set the table for seven.”
“Thank you, Bonnie. Let me set the table. I want to help. You shouldn’t have to do any extra work because I’m here.”
“Thank you, Greg.”
I went to my bedroom and took off the bathing suit, rinsed off in the shower. After I dried off I excitedly put on the panty. As I looked in the mirror I marveled at how nice it was to wear a panty. The fabric was soft and thin. There were lace decorations at the top of my thighs and a little bow at the center on the waistband. The panties were similar to a couple of my mom’s panties.
A sudden feeling of longing to fully dress as a girl came over me. Yes, the panty was nice, but it was incomplete. At least the bathing suit was whole and made me into a girl. A panty by itself wasn’t enough. I had fallen very far and deep into my need to be a girl. Where I had been satisfied by my halfway scheme of playing with my mom’s clothes, now, all of a sudden I wanted more. I craved a chance to dress up fully. Tomorrow, I’ll stay in the bathing suit all day long!
I put on my shorts and top and went downstairs to set the table.
***
Tom, Dick, and Harry showed up on time. Bonnie introduced me to them as her ‘little orphaned neighbor boy.’
“His grandma fell and his parents had to rush off to help her leaving him as my little charge.”
“I hope your grandma’s okay,” Tom said.
“Thanks,” I said.
“How many minutes did they give you to pack?” Bonnie asked.
“Not even ten minutes. They were rushing to get the last flight of the day to Miami.”
“Lucky Bonnie could take you in,” Tom said.
“I know!” I said.
The doorbell rang and it was the pizza delivery guy. Tom paid and we sat down to have dinner. Everyone had a beer except me. When dinner was over Tom said, “It’s time to swim!”
“Chicken fights!” Harry said.
The three couples got up from the table and I insisted on cleaning up. “Go on and swim,” I said.
“Greg, I’ll let you clean up but I want you to join us – in the pool,” Bonnie said.
“But, you know …”
“It’s all right Greg. You can wear my suit in front of Tom, Dick, and Harry. They’ll be as blasé as Maive and Jill. I guarantee it.”
“Okay,” I said, glad that she had insisted.
“I’m expecting our friend Angela to come by for a swim. Her girlfriend, Cynthia, recently had to move to California with her family and she needs some cheering up. You’ll like her.”
“She’s gay?”
“Yes. She’s quite a woman Greg. I wouldn’t be surprised if she could take on Tom, Dick, or Harry in arm wrestling or fighting or anything.”
“Wow,” I said.
“But she has a sweet side as well.”
I washed the plates and cutlery and otherwise cleaned the kitchen and dining room. I looked out into the backyard where the pool was lit up and Bonnie and her friends were having a chicken fight. The girls were sitting on the shoulders of their boyfriends and they were trying to knock over the other couples. It looked like great fun.
I changed into the pink bathing suit and went outside with my towel partially covering me. I felt uncomfortable to be seen in front of the boys, but I was more afraid of disappointing Bonnie. I took a seat next to the pool. After a few minutes I felt silly trying to hide myself and put the towel down. For this evening I’d trust in Bonnie and be myself. Fully exposed wearing her bathing suit I wondered if I was really the girl that I felt I was. Was being a girl in the mind only, or was it necessary to have breasts and a vagina? I didn’t know.
I watched the action in the pool until a woman who I assumed was Angela arrived wearing a simple black tank top bathing suit and carrying shorts and a towel. Bonnie got out of the pool to greet her. “Hey Angela!”
“Hey Bonnie.”
“I’m glad you could come!”
Tom and the others called out their greetings to Angela and she waved at them.
“This is Greg, my little orphaned neighbor boy.”
Angela smiled, “That’s quite a bathing suit Greg is wearing.”
“He’s staying with me while his parents are away and I had to loan him a bathing suit. Doesn’t he look good in it?”
“If you mean as a girl, I have to agree,” Angela said.
“Do you really mean that?” I asked.
“I thought you were a pretty girl until Bonnie said you were Greg,” Angela said.
Angela was several inches taller than me. Most surprising was her muscular biceps, shoulders, and calves. She looked like the kind of woman who worked out in gyms to develop her musculature.
“We’re having a chicken fight in the pool,” Bonnie said.
Angela turned to me, “Chicken fights are fun, Do you want to form a team with me?”
“I’ll have to sit on your shoulders. I could never hold you.”
Angela laughed. “It’s always girls on top, Greg.”
“Oh, I see, you mean I’m the girl?”
“Obviously.”
“Sure, that would be neat,” I said.
Angelo took my hand and led me into the pool. She effortlessly hoisted me up to sit on her shoulders while she held my legs. Bonnie climbed back up onto Tom’s shoulders. The four teams went to different corners of the pool and then Bonnie signaled the start.
The four “horses” raced to the middle carrying their girls on their shoulders.
Jill on top of Dick grabbed my arm and wrestled me sideways. I tried to pull away from her but she was too strong for me. Before I knew it she had me falling off Angela into the pool.
“I’m sorry Angela,” I said. “I couldn’t budge Jill, she’s so strong.”
“It’s okay, Greg, we’ll do better in the next round.”
We watched as Jill and Maive went at each other with Bonnie sneaking up to pull them both off into the water.
“And once again, Tom and Bonnie are victorious!” Bonnie said.
We regrouped and went at it again. This time I got tangled up with Bonnie, Maive, and Jill. The four of us were locked together. Bonnie had me in a bear hug trying to unseat me while she was being held by Jill and Maive. The four of us were falling off together when Angela caught me on my arm and held me up as Bonnie, Jill, and Maive landed in the water.
Angela lifted me up and over her head and lowered me into the water. “We won!” she yelled and wrapped her arms around me and squeezed me in celebration. The solidity and power of her embrace was sobering testimony to how far removed I was from competing with her for the masculine role. I felt like a mouse to her remarkable strength.
As we continued to play several more rounds of the chicken fights, I couldn’t help but admire Angela’s good-natured charm. She made me feel special and she liked me. I even wondered if she had sexual feelings for me. Not that she saw me as a boy, but as the kind of girl that she was attracted to as a lesbian. That thought that I could be the feminine object of her desire stirred up my own sexual feelings. How I would love to be Angela’s pretty girlfriend.
When we had enough pool time, we came inside to dry off and change back into our clothes. I went upstairs to my room to change and was sad to relinquish the bathing suit. While wearing panties was nice I’d unfortunately be back to wearing my boy shorts and top. I was standing in the middle of the room wearing the panties and feeling forlorn when Bonnie came to my door and said, “Greg, come with me. You should get dressed with the girls.”
I joined Maive and Jill in Bonnie’s bedroom and wondered why Angela wasn’t there. Was she changing with the boys? Or by herself?
“Angela’s not changing with us girls?” I asked.
“No, it takes her just a second to change, like the boys,” Bonnie said. “No makeup or any of that. She’ll be waiting downstairs for us girls to get fixed up. What do you think of Angela?”
“I love her, she’s so nice! And strong!”
“She really likes you too,” Bonnie said.
“She does? That’s great.”
“Jill, Maive, and I think that the best thing for Angela right now is for her to have a rebound relationship. That would get her going again. Perk up her spirits and then she can move on from there to find another love.”
“A rebound?”
“It’s the first relationship after a painful breakup. It helps someone to get past the hurt they’re feeling. It’s probably not going to end up being long term. For that a person needs a clear head and good spirits to make a fair judgement about the next person they might fall deeply in love with.”
“You think I should be her rebound?”
“You’re so smart Greg,” Jill said. “That’s exactly what we think.”
“But I thought that Angela dates girls.”
“Hello, Greg. For the last hour or so you’ve been a girl, haven’t you? Angela even said as much when she saw you in that bathing suit.”
“So you mean I could be her girl rebound?”
“We’re just throwing this out there in case you might like it. You see Cynthia was a feminine girl. Very much the kind of cute young thing that Angela goes for, and you are remarkably similar to Cynthia.”
“So what do I have to do if I’m to be Angela’s rebound girl?”
“Just be yourself,” Maive said, “and of course we’ll gussy you up to be so pretty that Angela will swoon for you!”
“Wow! So you’ll dress me like a girl?” I asked.
“Yes, something pretty that Angela will like,” Bonnie said.
“This will be so much fun,” Maive said.
“We can dress Greg like he’s a life-sized doll,” Jill said.
“How do we make Greg as pretty as possible?” Bonnie said, thinking out loud.
The three girls stepped out of their bathing suits while they discussed how I ought to be dressed. I watched in awe as they dried off with towels. Bonnie noticed my expression and laughed and said, “Greg, we’re all girls here. No need to be modest!”
“Sure,” I said having a near heart attack looking at their three beautiful naked bodies. Their vaginas were especially intriguing besides their breasts. I watched transfixed while they put on their panties and bras, stepped into their skirts, and put their tops on. The scene in front of me was one of those images that can never be erased from one’s memory. Every aspect of their womanly bodies and how they got dressed was made into indelible images in my mind. Their pretty vaginas, their breasts, the bras being slipped over their boobs. Panties wiggling up their legs covering their rear ends. It was sensory overload.
When the girls were dressed, Jill said, “We should start with Greg’s bra. Do you have an old lacy bra Bonnie?”
“You’re right. Greg should wear the sexiest lingerie. Angela will love that,” Maive said.
“I think I can find a lacy pink bra for Greg,” Bonnie said. She looked in her dresser drawer and fished out a pink, full coverage bra. “This one should be perfect. It’s the same pink as Greg’s panties! I’ve even got falsies he can wear with the bra.”
Bonnie handed the bra to me and said, “Do you need help putting it on?”
“Maybe a little, It’ll be my first bra.”
“No need to be shy. Our moms showed us how to put on our first bras. There’s a few different techniques, but we’ll stick to the easiest.”
Bonnie showed me how to align the hooks in front with the cups in back, then swivel it around and put my arms through the straps. Then she inserted the breast forms in the cups and I was dizzy with excitement. A bra and panty! I was finally on the way toward fulfilling my most secret desires. I wondered if Angela would end up seeing me in a bra and panty.
“God should have given you boobs,” Jill said admiring me. “You have the perfect figure of a young girl!”
“Now what, Bonnie? Girdle, or garter belt?” Maive asked.
“What would you like, Greg?” Jill asked.
“Can I see the girdles?” I asked.
“Sure,” Bonnie said. She extracted a panty girdle and two open bottom girdles from her dresser.
“Oh definitely take the dark pink one,” Jill said. “It’s close to matching your bra.”
“She’s right,” Maive said.
“Here, Greg,” Bonnie said and handed the dark pink open bottom girdle to me.
“You’re sure you don’t mind me wearing your girdle,” I asked Bonnie.
“No, not at all. I don’t wear girdles often.”
I stared at the girdle in my hand, not sure what to do.
“First unzip the side zip,” Bonnie said, and laughed, “It’ll be a lot easier to get on.”
“Thanks.” I undid the side zip, stepped into the girdle, and pulled it up and over my tush until it reached my waist. It was a bit snug.
“Fasten the inner clips and then zip it up,” Bonnie said.
There was a row of clips underneath the zipper and I fastened them one-by-one and then it zipped up easily to my waist.
“You have such a nice shape,” Maive said. “Are you sure you’re a boy?”
“He can’t be, Maive,” Jill said, “not with a figure like that.”
“You’re making him blush,” Bonnie said.
It was true. The flattery was inflaming my excitement.
“Before you put on stockings we’ve got to do your makeup and apply finger and toenail polish,” Bonnie said.
“You mean put polish on my finger and toenails?” I asked.
“Most def,” Bonnie said.
“But what happens when I go to my math class?”
“What would you do if you saw a boy with pretty pink polished nails?”
“Nothing, I guess,” I said.
“So that’s your answer. They’re your fingers and you can do whatever you want with them.”
With that I sat still while Bonnie put pink nail polish on my fingernails and Maive did the same for my toenails.
“Jill will do your makeup,” Bonnie said. “She’s really good at it.”
Jill worked first on my eyes and then my cheeks and lips. She spritzed my neck with Escada perfume and I was overwhelmed by the lovely scent. Jill got a brush and worked on my hair as best she could. It’s not short, but it has a way to go to be the length of a girls’.
“How’s that?” Jill asked Bonnie and Maive.
“Insanely cute,” Maive said. “Give Greg a mirror.”
Bonnie handed me a mirror and I was shocked to see how much Jill had femininized my face.
“Do you like it?” Jill asked.
“Do I ever! You’ve made me look like a girl, haven’t you?”
“That was the point, Greg.”
“Now all that you have to do is grow out your hair,” Maive said.
“Sure, I can do that,” I said.
She fished a pair of nude stockings from her drawer and rolled up the first one. I sat down and she had me stick my foot out toward her. She put the end of the stocking over my toes and gently unfurled it up my leg. Then she fastened the garters and repeated the same steps for my other leg.
“These are fine shear stockings,” Bonnie said, “be careful with them.”
“How do I do that?” I asked.
“Walk the way girls walk – with a sense of where your legs are at all times,” Bonnie said. “Take smaller steps and don’t be rambunctious.”
“Think of your legs as being gorgeous – which they are – and that you love showing them off,” Jill said. “That’ll help prevent you from snagging your stockings on something.”:
“I’ll do my best! Now I can wear a dress?” I asked eagerly.
“Yes. You’re now ready for a dress,” Bonnie said, “and I know exactly the right one. It’ll drive Angela wild! You’ll be so stunning in it.”
Bonnie entered her closet and came out a minute later holding a pink dress. “It’s from my pink phase. I wore this at my cousin’s wedding a couple of years ago.”
“It’s adorable,” Jill said.
“Perfect for you Greg,” Maive said.
“Of course it needs a crinoline,” Bonnie said, “and I have a white one that you can wear with it.”
I was surprised by how pretty the dress was. It was in a distinctive 1950’s retro styling. Pink with a marvelous skirt that puffed out all around. I’d seen dresses like this in old movies from that era as well as rock and roll TV shows. Bonnie held the dress up in front of me and I exclaimed, “Oh my God, Bonnie, this is so much the perfect dress!”
Bonnie instructed me to raise my arms and she lowered the dress over my head. When it was in place she zipped up the back. I stepped into the white crinoline and moved it up to my waist. Bonnie adjusted the bodice to accommodate my breasts. I stood in front of the three girls dressed in the pink party dress frozen in place with an overwhelming feeling of excitement.
“Here, raise your right foot.” I lifted it up and Bonnie put a white high-heeled shoe on my foot and buckled the delicate strap that went around my ankle. She did the same with my left. Now I stood in place raised up a couple of inches.
“Greg should wear an ankle bracelet,” Jill said.
“Good idea,” Bonnie said. She found one with a thin gold chain and some shiny stones dangling from it and put it on my ankle.
“He could use a necklace and some clip-on earrings, too,” Maive said.
“Right!” Bonnie said. She found a pearl necklace and put it over my head onto my neck and then clipped two dangly earrings with pearls to my ears.
“Absolutely beyond adorable, Greg,” Maive said.
“You’re as pretty as any flower girl or bridesmaid I’ve ever seen,” Jill said.
“What a beautiful and delicate flower you’ve become, Greg,” Bonnie said. “This is better than I ever imagined it would be!”
“You look like a princess!” Maive said.
“Tell us how you feel Greg,” Jill said.
“I, I, …, the truth is, I feel like I’m a girl,” I said. “In every way! I love wearing a bra and a girdle and the stockings feel so great on my legs. The dress is so pretty and the heels are nice to wear. They make me feel so grown up!”
“This is great Greg,” Bonnie said.
“I think you’re exactly the sort of girl that Angela prefers,” Maive said.
“Oh yes,” Jill said. “She’s going to eat you up Greg.”
“Eat me up?” I said plaintively.
“Not literally,” Bonnie said laughing, “but as an object of her sexual desire. I bet she’ll get all goo goo eyed over you!”
“Wow,” I said.
“Let’s go down and show you off to everybody,” Bonnie said. “It’ll be fun to see how the boys flip out over you and watch Angela go bonkers!”
“I’m a little unsteady in the heels,” I said as I took a few steps.
“It’s okay. Just walk slowly. All girls have a learning curve to get through in order to feel comfortable in heels!”
With Bonnie in front of me on the stairs and Maive holding my hand and Jill behind me, I carefully negotiated the stairs down to the living room.
Tom was the first to see me and exclaimed, “Wow. Greg is hot!”
Dick and Harry turned to look at me, “What a cute little princess,” Dick said.
“I’d never believe that was Greg if I didn’t know better,” Harry said.
Angela stood up to get a good view of me. “Oh my, you’re beautiful Greg. Such a pretty dress! You’re gorgeous!”
“You think so?” I said.
“Come here, let me have a good look,” Angela said, and I walked across the room to her.
She took my hands and lifted my arms gazing at my dress. I watched her eyes staring at my shoes, along my legs, to my skirt and crinoline, up to my bust and finally to my face. “I love your lips. They’re luscious.” She twirled me around and then hugged me. “You’re the cutest little thing, Greg.”
“I’m so glad you feel that way,” I said.
Jill interrupted us by calling for everyone’s attention. After we quieted down she said, “Dick and I have to pick a song to use for our first dance as husband and wife.”
“So we wanted to use you guys to help us decide,” Dick said.
“I’ve got seven songs to play,” Jill said.
“Everyone dance and then give us your feedback,” Dick said.
“We’ll ask you to tell us which one you liked the best.”
“What should we be looking for?” Harry asked.
“The song that makes Dick the horniest,” Tom said.
“Don’t listen to him,” Jill said. “What we want is to know which song is the dreamiest, the most romantic. I’ve programmed them to play one after the other. Dim the lights Bonnie if you don’t mind.”
The room dimmed and Jill used her smart phone to broadcast “Unchained Melody” sung by the Righteous Brothers to stereo speakers. Angela held out her hand and I took it. She put her right arm around my waist and took my right hand in her left hand. Wearing heels I enjoyed being a bit closer to Angela’s height. The way she held me was unfamiliar and I realized that I was in the girl’s position. It felt exotic and further proof of how I naturally slipped into the girl’s role when an opportunity arose. I gently rested my left hand on Angela’s shoulder. Then I felt her guiding me. It was a gentle, but firm pressure mainly from her hand on my back that had me moving in sync with her movements. For the most part she led me in a slow circle as I felt myself losing any lingering resistance I had to the knowledge that I was a girl for all intents and purposes.
The three other couples danced near us. Angela’s firm hand on my back communicated that she was in control. I sensed her physical strength. She had a solidity and a muscularity that could be contrasted with the delicate movements and feelings that my makeover into a girl had excited within me. The longer I danced with Angela the more I understood that her power and control was bringing out my own femininity. My urge to be a girl seemed to rise with each passing minute until I was having trouble remembering that at the end of the day I was still technically a boy. As a girl I was inclined to behave like a girl – to do the things that girls do – and especially be a girl to Angela’s masculine control over me.
The song ended and “Can’t Help Falling in Love,” began with Elvis singing. Angela and I continued where we had left off, except now she held me close with her two arms wrapped around my back. “It’s so nice to feel your soft body,” Angela whispered to me. “I’m not crushing you am I?”
“No, I like the way you hold me. Your arms are amazing. It’s great that you’re so strong. I’m sure that I prefer strong women.” I rested my head against her shoulder and closed my eyes. Glimpses of a fantasy in which I was a real girl with all the right body parts flickered in and out of my mind. How nice it would be if I could offer Angela real breasts!
“Why do you like strong women?” Angela asked.
“Because I think you’ll be best able to appreciate my femininity.”
Angelo laughed. “I think you’re right. I love girls like you. Not afraid to be as feminine as they want to be!”
As we danced I decided that this evening I would remove all inhibitions I might have to being feminine. I’d open myself up to behaving exactly as girls behave. No worrying or thinking about my boy self. Just open up and be a girl!
Next Jill cued up the Rolling Stones, “Wild Horses” followed by Percy Sledge singing “When a Man Loves a Woman.” I fell into a marvelous dream world in which I was guided and controlled by Angela’s powerful physique. She was holding me tightly enough so that I could feel my breasts pushing into her. I wondered if her desire for me had something to do with the pain of her losing Cynthia – a chance to hold another girl and get some comfort.
Angela shifted her hands so each one was on my butt cheeks. She slowly increased the pressure and my lower body began to grind against hers. I couldn’t have resisted her even if I wanted to. Her grip was like iron.
“Am I holding you too tightly, Greg?” Angela whispered in my ear.
“No, I guess not. I mean …”
“I love your little body, Greg.”
“Thank you,” I said.
A minute later Angela said, “Is that what I think it is?”
“What?”
I felt Angela’s hand reaching down and under my skirts and up my leg to the front of my girdle. She felt around my girdle and underneath it into my panty and said, “Oh how cute that is! You’ve got a little boner in there. I was feeling a little bump and I was wondering what that could be.”
“I’m sorry. I can’t help myself. I’m kind of overwhelmed by you!”
“No need to apologize, Greg.”
Her hand returned to my tush. I heard Angela laughing and I asked, “What’s funny?”
“It’s just that I’ve always been attracted to girls and never thought about a boy like you who’s more girl than most girls. It’s really kind of funny that you have a penis. A vagina would suit you much better.”
“Really? You think I’m more feminine than most girls?”
“See how Bonnie, Maive, and Jill are dressed? Then look at yourself.”
“I can’t imagine why a girl wouldn’t want to wear a pretty dress like this!” I said.
“That’s the kind of girl I like,” Angela said.
“I never knew there were girls that liked girls like me.”
“I’ve always desired girls like you, but I never knew that I would desire a boy who is a girl like you! A boy with not a trace of masculinity about you – with the exception of your boner.”
“You don’t mind it?”
“Actually, no. I’m curious about it since I’ve never encountered one before.”
The next song came on, “Just the Way You Are,” by Billy Joel, and I got to wondering if there was anything I was supposed to be doing about my boner. Like hiding it?
“I really hope my bump isn’t a bother or disappointment to you!”
“It’s actually kind of neat because it shows me how much I’m affecting you.”
I squeezed Angela a bit harder to let her know that I was happy.
The next song was “Sleepwalk” by Santo and Johnny and the final one was “Smoke Gets in Your Eyes,” by The Platters.
Near the end of the dancing Angela said, “In the final analysis, there’s something about how cute you are in this pretty dress all puffed up with crinolines that goes right to my libido and gets me excited.”
“That’s sweet of you to say. I enjoy being pretty for you.”
“I thought I’d never meet a girl as pretty and adorable as Cynthia and now here you are. You have exactly the same kind of delicate, demure, feminine, persona that she does.”
“You’re going to make me cry!” I said.
The song ended and Jill thanked us for our patience in dancing through seven slow songs. “We’ll break for beers and snacks and then Dick and I can ask for your opinions of the songs.”
I excused myself from Angela to help Bonnie in the kitchen. Maive and Jill came into help also.
“It’s so neat how taken Angela is with you, Greg,” Bonnie said.
“Yeah, she said she likes girls like me!”
“That’s true. Cynthia was one of those girls that was always wearing pretty clothes and flitting about. That seems to be you also.”
“To tell you the truth Angela discovered that I had a boner while we were dancing.”
“Poor Angela!” Jill said.
“Why poor?” I asked.
“I’m just teasing. Angela probably never had to confront one before. Not like the rest of us girls.”
“What does a girl do when she encounters one?” I asked.
“Run to the hills!” Maive said and the girls laughed.
“No, Greg. You know, when boys get boners, it’s a signal that they’re ready to have sex.”
“It is?”
“What else could a boner mean?”
“I never really thought about it. So Angela thinks I want to have sex with her?”
“God no, Greg,” Jill said. “She knows you’re not ready for sex. You aren’t, are you?”
“I can’t imagine what that’s like. I mean I know that I’m supposed to put my thing inside a girl’s thing but how does that work? It’s kind of confusing.”
“You are beyond precious, Greg,” Maive said.
“I would suggest that as a first step you and Angela use your hands to explore each other’s things as you call them.”
“You mean she could touch my … my … my penis?”
“Exactly, and you could touch her vagina.”
“Wow. What happens when I touch her vagina?”
“If you touch it the right way it it’ll feel good and she’ll want you to keep touching it. I bet she’ll train you into being good at it.”
“Do I have to train her how to touch my thing?” I asked.
“I doubt it, Greg. They’re pretty self-explanatory. A woman’s vagina, on the other hand, is largely like the far side of the moon to boys. They have no idea what’s going on there.”
The girls laughed uproariously.
“I hope Angela can teach me. I really want to make her feel good.”
“Don’t get ahead of yourself Greg. There’s no reason why you and Angela have to have a sexual encounter. Remember, only do what’s right for yourself.”
“This is such great advice. I’ll try to remember everything you told me.”
I helped Bonnie and the others distribute beers and bowls of pretzels to the living room and then sat down next to Angela on a loveseat. Jill led a discussion on the songs. She asked us to pretend we were getting married to our dance partner. Which of the songs would we pick for our own wedding? Jill’s remarks set me off thinking about what kind of marriage I would be happy with. Would I be the bride or the groom? Regardless of that, I knew that I’d prefer wearing a bridal gown as against a suit and tie. But that meant I clearly wanted to be the bride.
I whispered to Angela, “Do you think when I get married one day I could wear a bridal gown?”
“Yes, of course, Greg. Obviously, a man’s suit wouldn’t make any sense for you.”
Angela put her arm around me and hugged me and I said, “I hope I meet a woman like you one day – when I’m older – who asks me to marry her.”
“With luck you will, Greg. You’re such an attractive young girl I think some lucky woman will snatch you right up.”
The evening was turning out to be tremendous fun and a wonderful opportunity for me to be a girl. I was spreading my girl wings and I loved that Angela was encouraging me. For this night I would be the girl partner that Angela wanted. If she made sexual demands on me I’d step up to be the feminine girl that she needed.
Jill pressed us on which song we preferred and Angela and I agreed that our favorite was “When a Man Loves a Woman.” I asked Angela, “You’re the man, right? I mean between you and me?”
She laughed, and said, “When we danced I was in the man’s position and I was leading. You naturally gravitate to the girl’s role, don’t you? Well, besides any of that – I’m the strong one and you’re the weak one.”
“So I have to do what you tell me to do,” I said.
“You’re darn right!”
“I’m happy to!”
After Jill collected the data she thanked us. Bonnie dimmed the lights and dialed up the movie. I’d never been in the dark with a girl or a boy for that matter. The movie was going to be a pretext for the couples to have a make-out session. That would be a new experience for me, though I figured this was something Angela had done many times.
As the movie started Angela tightened her hold on me and I settled in leaning against her and resting my head against her shoulder. I observed the other couples holding each other affectionately. I enjoyed the coziness of being enveloped by Angela. My skirts were bunched up over her leg and I imagined that she liked looking at how my breasts stuck out.
Not long into the movie, I felt Angela’s finger gently guiding my chin toward her. She leaned in and kissed me on the lips, and our positions shifted to make ourselves more comfortable and we kissed steadily for a long time before Angela broke it off and resumed looking at the picture. She had put her tongue in my mouth. It was the very first time that I had kissed that way and I must admit that I felt transported to a sensual realm I had never been to before. I could see why kids liked making out.
I looked up and saw a satisfied smile on Angela’s face. A few minutes later I felt Angela’s hand working its way up my skirts toward my boner. I laughed quietly and said, “My girdle’s in the way.”
“I can sneak my hand inside it to take care of your boner,” Angela whispered.
“Can we worry about that later? I’d much rather make you feel good. Can you show me what to do?”
“Are you sure? I don’t want to take advantage of you.”
“You’re not taking advantage of me. More than anything I want to devote myself to making you feel good.”
Angela was wearing jeans. She unbuttoned them and lowered the zipper. Then she squirmed to lower her jeans and panties to the middle of her thighs.
“So what do I do?” I asked, looking down at her pubic bush that was somewhat obscured in the shadows.
“I’ll start you with your fingers. Later you can try your tongue if you have an impulse to do so.”
“Tongue? You mean I can lick you down there?”
“Yes.”
“That sounds neat.”
Angela laughed. “It is neat, Greg. It can be a lot of fun. I can even do it to you, at least theoretically. You have to understand that I’m not too familiar with your boy equipment. Actually, it might take some getting used to for me to put that thing in my mouth.”
“I’d hate for you to do something you’re not comfortable with. But right now I really want to make you feel good!”
“Okay, you’re right. Let’s concentrate on me! Rest your hand on my pubic bone and use your middle finger to enter my pussy very gently. First lick your finger! Good girl.”
Angela talked me through what would arouse her. First I massaged her clitoris until it hardened up. Once it was hard I ran my finger along it. Gentle swirly motions helped raise her excitement. After a few minutes I sensed her muscles tensing and her legs and hips convulsing. I found myself loving it. It was so much fun to get another person aroused.
Every so often Angela adjusted the location of my finger to make sure it was hitting the right spots. About fifteen minutes into it Angela audibly gasped and she whispered – so good Greg you made me cum!”
“That’s neat,” I said.
“Now we go for another!”
“I hope I can manage it!”
“You’re doing beautifully, Greg.”
I studiously guided my finger within Angela’s vagina enjoying its heat and wetness. Almost immediately she tensed up and grunted and I knew I had pleased her again.
She put her hand over mine and said, “I need a few moments to catch my breath!”
While we rested I glanced around the dim room and saw that Bonnie was on her hands and knees in front of Tom and her head was bobbing up and down. To my surprise a similar scenario was playing out with Maive and Harry.
I whispered to Angela, “What are they all doing?”
“It looks like blow jobs. Would you like to try that with me? Use your tongue in the same way you used your finger?”
“Sure, I’d love to try that.”
Angela took off her jeans and panties and spread her legs wide. I got on my hands and knees in front of her and put my tongue on the outer lips of her vagina. I don’t know what came over me but I thought I’d died and gone to heaven. Angela’s vagina was very welcoming and my tongue quickly pushed its way in to discover the delectable wetness within. Her hard clitoris loved to be caressed by my tongue, and with a happy clitoris, Angela was soon writhing with pleasure as I hit her best spots. She had a powerful orgasm and I sat back waiting for her to signal for me to resume my licking. Once she recovered she gently nudged my head forward again and I resumed my sweet dream-like reverie with my mouth and tongue lost in her bush and precious vagina. In a few minutes she had what seemed to be the biggest orgasm yet and when she recovered she said that was enough for now. I got up and sat back next to her while she put her panties and pants back on.
“What did I miss in the movie?” I asked and Angela laughed.
“Now I want to feel that thing of yours. Sit back and relax.”
I did as Angela said. She lifted up my skirts and her hand worked its way through a leg hole of my panties until it encountered my penis. “Got it Greg! The first time I’ve ever held one of these suckers!”
I wanted to laugh but the pleasure of her gripping my penis was so intense I was unable to do anything more than freeze in place.
“As much as I’ve heard about them, I guess I’m supposed to slide my hand up and back a little like this,” Angela said.
I felt Angela’s hand moving along my penis and I whimpered in pleasure.
“This feels good?” she asked me.
“Yes!” I gasped.
“Good. Look at that, I’m an expert already.”
Angela continued stroking me and suddenly I shot off.
She laughed. “That’s easy as pie! I didn’t have to do anything. A couple of strokes and my hand is all wet! Boys are simple.”
“Huh?” I said in a hurtful voice.
“What’s a matter Greg?”
“Boys are simple? I thought I was your girlfriend?”
“My bad. I’m sorry Greg. I got carried away. You’re my girl. No doubt about that!”
“Thank you.”
“Oh you poor dear! Come sit on my lap!”
I stood up and sat down on Angela’s lap and put my arm around her neck. I leaned in and kissed her on the lips and she put her arms around me and held me against her.
“My little girl, Greg,” Angela said. “How could I mistake you for a boy even for a second?”
“I don’t know,” I said.
“I’ll never make that mistake again. You’re so precious!”
The movie ended and Bonnie raised the lights back up. I got up off of Angela’s lap and sat down next to her. The other couples sat relaxed with satisfied expressions on their faces. Suddenly I was scared. The evening would soon be over. Angela would get up and leave. Would I ever see her again? What was to happen with me? Would I get to wear this dress again? Would I be able to still be a girl? These many questions buzzed around in my mind. I felt helpless and over my head into desires that I couldn’t hope to fulfill.
Angela turned to look into my face. “I sense you’re tensed up, Greg. Are you worried?”
“I’m scared that I will never see you again.”
Angela smiled and held me tightly against her. “I can come by tomorrow, have a real date. We’ll swim, then I’ll take you to dinner at a romantic Italian restaurant. It’s a week before I go back to college. We can plan some other dates.”
“I’d love that, Angela.”
“You still look unhappy.”
“What happens after that?” I said, choking up with emotion.
“You poor dear,” Angela said. “I’m going to miss you terribly, Greg. You’re exactly the kind of girl that I could fall in love with. I won’t deny that, but we can’t be together for now. In fact, we may never be together again after this week. It’s the way life sometimes unfolds. But there’s no reason why we can’t remain friends and I’ll be back from college every so often and none of us can predict the future. We’ll just live our lives – no pressure, no drama – and see what happens.”
I wiped away some tears and said, “So I’m your rebound?”
Angela looked surprised and said, “Rebound? You mean after Cynthia? I never thought about that. I certainly never thought of you as someone that I’d only see for a limited time. So the jury is out as to whether or not you’re my rebound.”
“I’m going to pray that one day I find out that I’m not your rebound,” I said.
“What a sweet thought, Greg,” Angela said.
I walked Angela out to her car. She held me and gave me a long kiss. It was long enough that I felt new pulses of pleasure forming within my loins.
“Chin up my dear girl,” Angela said. “Sleep well and I’ll see you tomorrow.”
“I can’t wait until you return,” I said, and watched as Angela drove away.
I walked back into the house smiling at the thought that the next day would be a very nice one regardless of what came after that. Bonnie, Maive, Jill, and their boyfriends would be getting up early to white water raft in a nearby river. After I was alone I’d straighten out Bonnie’s bras and panties and organize the rest of her clothes. That would take some time. Then I’d get myself ready for my date with Angela.
***
A short time later the boys left and I asked Bonnie, “Is it still okay if I sort your clothes tomorrow?”
“Yes, Greg. I’m counting on you.”
“Great. I’ll do my very best. Angela will come by tomorrow to see me. She invited me out for dinner, and … you see … I need a dress to wear. I’m wondering if you have any other dresses that you would let me borrow?”
“Greg, any dress that you find that you’d like to wear is okay, but don’t get tomato sauce on it!” Bonnie laughed.
“Thanks.”
“Now, us girls are going to have a pajama party in my bedroom. It’s what we always do after an evening with the boys. We swap stories about what was going on during the movie! It’s so much fun. I’ve got the perfect, cute pink negligee that you can wear. You’re going to tell us everything you did with Angela!”
I could barely contain my happiness. It was clear that a feminine world had opened up for me that accepted me as being one of their own. Today had been the first few steps into this wondrous place. Imagine how much it had to offer me for the rest of my life.
The End
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