It's been a while, had the itch, decided it was time to post something. Hope you enjoy it. More to come soon.
-J
I was sitting in the chair facing away from the mirror, my sister, Olivia, had been working on my hair for a little over an hour. She was trimming, and dyeing, and doing all these things and kept insisting “trust me.”
Finally it was the big reveal – she spun me around and what the hell had Olivia done.
“What the hell, Olivia?” I exclaimed, probably a little too loudly.
“It’s fine, Jamie, I always liked playing with your hair, it’ll grow back.”
“I look like a damn girl and you dyed it blonde!” I griped.
“That was kind of the idea,” Olivia responded. “It’s a long bob, or a lob, I wanted to try it out and your hair and face are perfect for it.”
“What am I supposed to do now? I have to go to the store after this.”
“Let me put a little makeup on you.”
“What? No way!”
“Seriously, Jamie, it’s not a big deal. You’ll look super cute and no one would ever think you’re a guy.”
“Thanks.”
“You know what I mean, you’ve always had a long hair and you’re not the biggest guy; and not to sound clichéd or anything, but you can’t grow a beard to save your life.”
I just frowned.
“Alright, just a little bit.”
Olivia grabbed her makeup bag and went to work on my face.
An hour later, I was at Shop-A-Lot, this big store that has everything, standing in the DVD section. I picked up a DVD and set it back down and noticed a guy was looking at me. He walked over and picked up the DVD I was looking at.
“Have you ever seen Monty Python?” he asked.
“Nope,” I responded quickly and started to walk away.
“Well, maybe we can watch it together sometime,” he said.
I stopped dead in my tracks, because this guy was asking me out.
“Ha, maybe,” was all I could muster.
“My name is Pete,” he said.
“Jamie.”
“Nice to meet you,” he said. “So, I- I’m not really sure how to do this, it’s been so long, but I saw you and I thought you were gorgeous. I had to come over and talk to you, plus you were looking at a copy of one of my favorite movies.”
“Well, thanks,” I blushed, I think.
“Do you think you’d like to go out to dinner with me?” he asked.
“Uh, I…” I stammered; then my brain exploded and it went into auto-pilot without my knowledge. “Sure, why not.”
Pete beamed and quickly pulled his phone out of his pocket, “Let me get your number and I text you later.”
I nodded, coolly, and gave him my number, my actual number.
When I got home, Olivia was already home and I already had three text messages from Pete.
“Olivia! I am going to kill you!”
Olivia came out of the kitchen with a microwave dinner and a glass of chardonnay – her usual – and cocked her head.
“What’s the matter?” she asked.
“I got asked out on a date!”
“Ha, who cares, you’ll be back to you after you take a shower, you’ll just have to figure something out with your hair, style it differently, it’s a little girly even without the product.”
“I said yes,” I mumbled.
Olivia laughed and nearly dropped her food.
“Oh my god, why?”
“I don’t know, I felt bad for the guy, he was nice,” I said. “He said I was gorgeous.”
Olivia laughed hard; again. “Well, Jamie, not going to lie, you’re pretty hot and you’re wearing those tight jeans and one of my hoodies, so you’re dressed essentially like a twenty-something girl.”
“Jesus Christ, Livy, what am I going to do?”
“Get dolled up and go on a date with a guy,” she said. “Or you can embarrass him and text him that you’re a guy.”
I gritted my teeth. “I can’t.”
“Then let’s go find you something cute to wear, shall we?”
An hour later, after shaving my legs and underarms, I’m standing in front of a full length mirror wearing a green dress. My hair, my sister had done something – pulled it up in back so that it has pieces framing my face.
I looked so much like a girl it was scary.
“God, you’re prettier than me,” Olivia said.
Pete came to pick me up at eight and we thoroughly avoided my nosy sister, despite her lurking around the corner in the kitchen.
“You look great,” Pete said.
“Thanks. So do you.”
I then decided by the end of this “date” I was going to tell Pete that I’m a guy and that this was wrong of me to do, but I didn’t want to embarrass him. I hoped that he’d understand and not try to kill me.
To be honest, Pete was really great company, aside from him complimenting me all the time and telling me how pretty I was. He told me he was a Silicon Valley guy who made an application about something that made him a lot of money and now he consults for other companies. I tuned out when he started talking about the other companies and the applications. When dinner was done, Pete had paid, and as we walked out he had linked his hand with mine. I felt something then that I didn’t think I’d feel, a tingling maybe. We went out to his car, he opened the door for me, and I climbed inside.
We pulled up in front of the house that my sister and I shared, and he put the car in park.
“Listen Jamie, I’m not used to all this, I haven’t been on a real date in a long time. I think you’re beautiful and funny and I’d like to see you again,” he said.
“Pete, there’s something-“ I unbuckled and turned in my seat to face him, Pete was already there and he had put his hand on my face.
“Can I kiss you?” he asked.
“I…” I didn’t respond, but he did so anyway.
We kissed for a moment, our tongues colliding in a haphazard fashion showing that neither of us had done it in a while. Finally, I put my hands against his chest and pushed him softly away.
“Listen, Pete, I have to tell you something before this gets out of hand,” I said. “I’m a guy.”
Pete smiled. “I’m not an idiot, Jamie. I know you’re a guy, but damned if you’re not the prettiest guy I’ve ever seen.”
“You knew I was a guy and you still kissed me!”
“I wanted to kiss you the day I met you and I knew you were a guy there, though, I’m sure no one else could tell,” he said. “It’s just subtle mannerisms you have.”
“I’m not gay, Pete,” I said.
“Either am I, but I had a really nice night tonight, and I’d like to see you again.”
“I don’t know, is that okay?”
“Sure,” Pete was disappointed; I could see it on his face.
“I should go,” I said.
I started to get out of the car, but something stopped me. I turned back to Pete and kissed him hard on the mouth. It was a kiss that we would both remember if it never happened again.
I quickly got out of the car and walked briskly up the walk to the front door. Once inside, I did that whole cliché thing where I leaned against the door and really thought about things for a minute.
To be continued…
I hope everyone enjoys this chapter, sorry it's taken so long. Hopefully the next chapter won't take as long. -J
I woke up the next morning and went into the bathroom and stared at myself in the mirror, my curly-ish hair was messy, but still very girly. I groaned at the sight of the raccoon eyes I had, because I hadn’t taken my makeup off last night. I wiped my face with a towel as best I could and went downstairs where my sister was making breakfast.
“Hey sis,” Olivia said.
“Shut up, Liv.”
“How was your date?” she asked.
I didn’t say anything.
“What’s the matter with you?”
“Nothing.”
“Well dish, tell me about your date,” she set a plate of eggs and bacon in front of me, and sat down at the table.
“It was fine.”
“Really, Jamie?”
“What do you want to hear?” I spread my arms wide “That we kissed? Like really kissed, and I initiated the second kiss!”
“You kissed twice?”
“Yeah.”
“Wow, I didn’t expect that.”
“Either did I, but it happened, and Pete wants to see me again.”
Olivia sat back in her chair and folded her arms across her chest. “Do you like him?”
“I… I kinda do,” I said. “But I’m a guy, and he’s a guy.”
“Sweetie, you don’t look like a guy right now.”
“But I’m a guy, god damn it.”
Olivia laughed.
“But, you really liked how it felt to be a girl, didn’t you?”
I groaned.
I caved a day later and texted Pete, he called me a few hours later, and we chatted for a few. We made a date to go to the movies that night.
Olivia helped me get my hair ready for the date, but she made me do my own makeup, “If you’re going to be a girl, you’ve got to learn how to be a girl,” she said.
Pete picked me up at eight and we went to see some romantic comedy, but truth be told, we didn’t see much of the movie. Pete’s hand made his way around my shoulder, I lifted the divider and leaned into him. He looked down at me, lifted my chin up, and kissed me. The kissing didn’t stop until I pulled away.
“Pete,” I gasped, “I can’t breathe.”
We both laughed and watched the rest of the movie.
Later, in the car, in front of my house, we went back to kissing. My hand made it’s way up Pete’s leg where I felt, for the first time, his manhood and how aroused his was. It nearly stopped me, but I left my hand on his penis, rubbing slightly.
“Come home with me,” Pete said through breaths.
“I don’t…”
“No, you’re right. Jeez, I’m sorry,” Pete said wiping my lipgloss off his lips.
“Pete…”
“Jamie, I really like you.”
I laughed, “I could tell.”
Pete turned and kissed me lightly on the lips.
“I have to go into the office tomorrow, but what about Friday, I cook you dinner at my place.”
“That sounds really nice, I’d love to.”
We kissed again, a long, passionate kiss, and I opened the door and slipped outside into the night. I smiled at him, “Text me your address, I’ll see you Friday.”
Inside, I went inside and kicked off my flats and sat on the arm of the couch next to Olivia.
“Good date?” she asked; smirking.
“Really good, actually.”
“I assume this is going to continue.”
“He’s going to cook me dinner at his house on Friday,” I said, smiling.
Olivia clicked off the TV and patted the couch next to her, I sat down, smoothing out my dress.
“Jamie, how far are you willing to go with this?” she asked.
“What do you mean?”
“You’re going to his place. What do you think is going to happen there?” she looked at me inquisitively.
“I hadn’t thought of that, but I really like him,” I said.
“Enough to have sex with him?” Olivia asked. “That’s what you’re in for if you go to his place, Jamie.”
On Friday, I pulled into the driveway of a pretty nice house and got out of the car. On the way, I stopped at a CVS and bought a bottle of Wine. The girl at the counter looked really confused by my ID, but I guess I looked enough like my picture where she didn’t care.
I walked up the steps to the house and rang the bell. Pete answered and ushered me into the house, took the wine from me, and immediately gave me a kiss on the lips.
“I missed you,” he said.
“I missed you too.”
Dinner was an Italian dish that his mother had taught him to make for our date, and it was delicious. After dinner we sat on the couch talking, which ultimately let to kissing, which ultimately led to more fondling. Pete was almost immediately aroused when I touched him down there. I continued to stroke him through his pants. We kissed more, until I pulled away. I began unzipping his pants and pulled his boxers down and his penis sprang out. Other than porn and the occasional accident in the locker room shower, I had never seen a penis up close other than my own.
I put my hand around his penis and began stroking him while kissing him deeply. Our tongues colliding with passion. I pulled away again and dropped to my knees in front of Pete. I pulled his pants down further and rubbed his legs with my hands.
“Jamie…” Pete said. “You don’t have to.”
“I want to,” I said, smiling up at him.
I then proceeded to put my mouth on Pete’s penis, stroking it while I sucked him. Pete put his right hand through my hair to the back of my head and pulled me deeper onto his shaft. I felt myself becoming aroused in my panties. I tasted precum first and Pete let go of my head, leaning back on the couch.
“Babe, babe, I’m going to come,” he said.
And he did and I swallowed his cum. I pulled back off his lap and wiped my mouth.
“Holy shit, Jamie.”
“Must’ve been the wine,” I laughed. “Did you like it?”
“Like it?”
Pete grabbed me and I straddled him on the couch, I flipped my hair to one side and he kissed me passionately. I felt him getting hard again, pushing against my leg.
“Pete, I’m not ready for that,” I said, slipping off of him onto the couch.
“I, wow, I’m sorry, I got carried away,” he said, sheepishly.
“Pete,” I said, “I will be ready, but I’m not sure when, but… the way you moaned when I did that…” I pointed to his still exposed manhood. I put my hand back on it and he shuddered.
“I really liked doing that for you,” I said. “I’m glad you liked it.”
To Be Continued…. In… “The Wedding” (No, not their wedding)
So, it's been a very long time, prior to this my name was JanisIsForever, but unfortunately could not get a password reset to come through on the email I used, so I posted it under this username.
This will be the end of this series, maybe something in the future, but for now Jamie's story is up to your imaginations.
Thanks!
Also, here's the links for part one and part two:
https://bigclosetr.us/topshelf/fiction/77396/jamie-part-i-ha...
https://bigclosetr.us/topshelf/fiction/89885/jamie-part-ii-a...
Jamie – Part III – “The Wedding”
Things were going strong, Pete and I were spending a lot of time together, he didn’t have to go to the office much since he was a tech start up millionaire (did I forget to mention that?!), so we were together all the time. He told me about his job on our fourth date.
“So, I don’t know exactly how to tell you this, but I feel like this is getting serious,” Pete said, across a table at an Italian restaurant. “I’m… kinda rich.”
I was slightly taken aback by what he said, but not shocked. Pete did pay for mainly everything, even though I did offer, he refused.
“Rich, how?” I asked.
“I started a company with a few friends and we sold it for…a few hundred million…”
I choked.
“What?” I was shocked.
“Yeah, I don’t know why I didn’t tell you, babe.”
Oh, he called me Babe. I liked when he called me Babe.
“I’m not mad or anything, Pete, I’m just shocked. No wonder you never let me pay for anything.”
“Why would I? I’d rather spend my money on doing fun things with you or buying you nice things. What’s the point of having money if I don’t spend it on someone I love?”
Gulp.
“Uh…”
“Did I just…”
“Yeah…”
“I… uh…”
“I love you too,” I said, I leaned across the table and kissed him.
When I returned to my seat he sighed a sigh of relief.
“I have something to ask you?”
“We haven’t been dating that long.”
“No, not that,” Pete laughed. “But ironically it is a wedding. A friend of mine is getting married next month and I was wondering-”
“Of course, I’d love to.”
“You’re sure.”
“Are you sure?”
“One hundred percent.”
That night we went to his place and started watching a movie, but our hands started traveling. We started kissing and soon I was straddling him again grinding on his hard-on.
“You get me so damn hard,” he said, breathing heavy.
“Good,” I said, reaching down between his legs and rubbing his dick with my hand.
“I want you,” he whispered.
“I’m...not ready…” I said and slid off of him.
“Babe, I’m sorry. I didn’t it mean it like that.”
“I know…” I said looking down at my hands. “I just don’t know when I’m going to be ready.”
“Jamie, this is a big thing. I’m not rushing you to do anything you’re comfortable doing.”
“Yet,” I corrected. “Not comfortable yet.”
“Okay. Yet,” Pete said.
Pete stood up and walked to the kitchen and came back with two bottles of water.
“Do you want to spend the night?” Pete asked. “I just want to hold you close to me.”
Awwww.
“That sounds really nice,” I said.
I stood up, removed the bottles of water from his hands, and lead him into the bedroom.
“Let me do something I am comfortable doing.”
The next morning, I woke up to the smell of coffee and bacon. I wore a pair a panties and one of Pete’s shirts to bed and padded out to the kitchen where Pete was making breakfast.
“And you cook? I’m a lucky girl.”
“Good morning, beautiful, you sleep okay?”
“Never better,” I said, and that wasn’t a lie, we spooned the entire night and I slept like a baby. Pete woke me up a few times with a poke in my butt area, but that was par for the course.
I went around the counter and stood on my tippy toes to give him a kiss, “I’m sorry if you’re disappointed about last night.”
“Babe, why on earth would I be disappointed?”
I shrugged, “Because we didn’t do it.”
“Jamie, I’m not in this to have sex with you. I mean, I’d like to, at some point, when you’re ready, but I love spending time with you…” he leaned down, and spoke lower, “I also like the other stuff we do.”
I giggled. “I like it too.”
I went home, and took a shower, when I got out Liv was sitting on my bed waiting for me.
“So, spending the night now, huh?”
“I would say nothing happened, but something definitely happened, just not what you’re thinking,” I was trying to beat around the bush.
“Jamie!”
“What?!”
This is all my fault, I did this, I created this whole situation.
“Liv, I’m really happy right now, it’s not like I’m lying to Pete or he’s lying to me,” I said, defensively. “Maybe…”
“Maybe, what?” she crossed her arms over he chest, a look I’d seen many times in the past.
“Maybe this is who I’m supposed to be.”
“You think you’re supposed to be a woman now?” she asked, incredulously.
“I don’t know! I like it, I love it actually, I love him, Liv.”
Her eyes went wide, “Love him? You’ve been dating for two months.”
Two months? Had it been that long?
“He told me he loved me and… I feel the same way.”
“Jesus Christ!” she threw her arms in the air and stormed out of the room.
After I got dressed, I did my makeup and hair, and went downstairs. I figured it’d give her time to cool off. She drinking a cup of coffee at the kitchen table, I sat down across from her.
“I’m sorry, Jamie, I overreacted,” she said.
“Liv, maybe you’re right to overreact, this is all really weird and new. I’m sure from the outside looking in, it’s super weird, but from where I am it’s fun and exciting and honestly… scary as fuck.”
Liv laughed out loud, “I bet.”
“Being a girl in a relationship is nerve wracking. I don’t know what I’m doing half the time and have to rely on… things that… have been done to me.”
“Oh my god, you didn’t!”
I could feel my face redden, “Quite a few times...actually.”
“Jamie! You whore!”
“OLIVIA!” I yelled.
“I’m kidding, but also… that’s definitely new for you. Holy shit.”
“We haven’t done… the other thing, yet.”
“But…”
“I want to, with him, for sure. I’m just really scared.”
“You should be, you’re in uncharted waters, girl.”
I laid my head on the table and sighed, “I know he’s been really patient and he keeps saying it’s not a big deal, but it was a big deal when I was-”
“A dude?”
I glared at her.
“I’m just saying, you’ve got a unique perspective here.”
I nodded, “He invited me to a wedding out of state, so we’ll be spending the night in a hotel. Oh, and I forgot to tell you, he’s rich.”
“What? Like, how rich?”
“Like, rich, rich.”
“Better hang on to that one, girlfriend.”
Later that week, Liv and I are out dress shopping for this wedding, and we run into a girl that we both knew in High School.
“Jamie?”
“Uh…”
“Oh my God, you transitioned?”
Blushing, “Not exactly. This is all kind of new.”
“You’re gorgeous, I almost didn’t recognize you!”
A few more minutes of small talk and we were on our way out of the store with a blue strapless dress and a matching set of heels.
“You know I have very limited experience in heels,” I told Liv.
“You me no experience,” she said.
“Yes.”
In the car on the way home Liv patted my leg, “You okay?”
“Yeah, why?”
“Your secret’s out,” she said.
My heart sank. “Fuck.”
“That girl, whatever the hell her name was, had the biggest mouth in school. By now, half the school knows,” she said.
I just nodded and laid my head against the window.
“Well, you’re in it now, girly. No turning back.”
The wedding was a few hours away so I didn’t dress for the wedding, I decided I’d get ready in the hotel. My hair was touching my shoulders now, which was a really weird feeling for me, but also gave me a different way to style my hair.
Pete arrived at the house and honked the horn, Liv was at work, so I rushed out with my overnight bag and my dress. He placed the items in the cars trunk as I climbed in the car.
“Hey babe,” he said climbing in, he leaned over and gave me a quick kiss on the lips.
“Hey yourself,” I said. “How’s work?”
“It’s work, I’m glad to get away, to be honest. It’s been keeping me too busy.”
I nodded. “Well at least we get to spend this time together, right?”
“Of course, I’m super excited, I rented us a suite and I believe it has a hot tub or a Jacuzzi, or at the very least a large bathtub.”
I grinned. “Sounds fun.”
About an hour into the trip, Pete put his hand on my leg, and gave it a squeeze. I smiled up at him and upped the ante by running my hand along his package which almost instantly became aroused. The fact that I, personally, could do that to him, was something so ridiculous to me.
“Babe…”
I shushed him, and unbuckled my seat belt, leaned over, and unzipped his pants. I pulled his member out through the hole in his boxer shorts and proceeded to give my man road head. He came in my mouth and I spit it into an empty water bottle, I was not riding with that in my stomach for the next hour and a half. I reached over, zipped him up, and gave him a pat on the knee.
“Jesus Christ,” he sighed. “You’re… something else.”
“Love ya.”
“Love you too.”
The wedding was a blast, dancing, and drinking, and meeting people I’ll probably never see again. I had a lovely conversation with a little girl who said she loved my hair, I had done it in an updo with curls hanging on either side framing my face. Liv had said it fit my face structure really well, so I went with it. The dress fit really well and I guess I have my mother’s hips, because it was snug as all get out.
Pete introduced me to everyone as his girlfriend, which was really weird, but also really exciting at the same time. We drank way too much, had way too much PDA, but no one seemed to mind.
After the wedding we’re up in the hotel room kissing heavily and Pete is removing my dress. It slides down around my ankles revealing my padded bra, my panties, and I’m still wearing my heels.
“God damn,” he grabs me by the hips and pulls me close to him, kissing me deeply.
“Let’s go take a shower,” I say, biting his lower lip.
I make my way to the large bathroom pulling heels off in the process, The bathroom has a large walk in shower, I turn it on and pull off my bra and then my panties, which makes me feel self conscious for a moment, but I’m too drunk to really feel it.
I step into the shower and stand under the hot water for a moment. Pete opens the door to the shower, stands there nude, staring at me.
“Are you coming inside?” I asked, smiling at him.
“Yup,” he says, and quickly walks into the shower shutting the door behind him.
He stands me behind me while I soap myself up, and runs his hands along my body, stopping on my butt which he squeezes. I giggle and turn my head to face him and he kisses me deeply. Our bodies pressed up against each other. I use bar of soap and rub soap on my butt and my back and he uses his hands to spread it around those areas, where he stops near my butt and fingers my butt hole.
I groan, and reach behind me, and feel how hard he is. I take his hard on and rub it against my backside where the tip of his penis touches my hole. He pushes a bit, and I’m taking the lead here, I decided that I want my man and I want him right now. I turn around throw my arms around his neck, “I want you.”
“I want you too,” he whispers.
He reaches behind me and turns the water off. We both exit the shower and I lead him into the adjoining bedroom, where I push him on the bed, and mount him. We rub our bodies together for a moment, before we turn side by side, where I’m on my right and he’s on his right, and he fucks me for the first time… then the second time… and in the morning for the third time.
Needless to say, I was very sore, and told him while we were riding home, we needed to not do that again for a little while.
“We got carried away,” he said.
“Pent up…sexual frustration,” I confirmed.
“I love you, Jamie.”
“I love you too, Pete, now take me home, I need to lay in bed for a week.”
Pete laughed. “So… no road head.”
“I will bite it off,” I said, then smiled.
“Hey now.”
The End.
Sorry that it’s in a different spot, could not get a password reset to save my life.