John Becomes Jen

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
jackie_em
jackie_em
1,560 Followers

...................................................................................................

I found study groups for some of my classes and one group included Roni who was very smart. After a while it seemed to mostly be Roni and I studying together for that class. Roni was about my age but had shorter hair and tended towards jeans and tops. She had a cute face and a nice shape, though she wore sports bras that flattened her chest somewhat.

She was fun and even flirty, though I felt sure nothing could ever come of that. We began to hang out and even went out together as two girls. While she flirted with me, she also flirted with other girls and even with boys. I wasn't quite sure what to make of that. Occasionally when we studied together, we'd study at my place. After one session, we began to talk.

"Jen, I never see you flirting with anyone."

"Yeah, I don't know. It just never seems quite right."

"Are you attracted to boys, girls, both, or neither?"

"Mostly girls, but there are issues."

"Your parents wouldn't approve of you with another female?"

"I'm not sure. But what about you? Who are you attracted to?"

"I guess I'm pan."

"You're attracted to cookware?"

"No, silly, gender and gender identification don't matter to me."

"I don't understand."

"Male, female, and trans -- all of them."

"Really?"

"Sometimes you seem to be really female, sometimes I think you're trans."

"I'm mostly female, except between the legs. Please don't tell anyone though."

"Because you're not sure who might be offended by that."

"Some folks don't like that."

"What if I said that didn't bother me?"

"I'm not sure what to say."

With that, Roni leaned forward and kissed me. I was kind of shocked and almost afraid to react, but she kept kissing me instead of pulling back and very quickly I began to kiss her. As we kissed, she pulled me closer and began to stroke my back. That felt good, but I was still fearful and wasn't sure how to react. I hadn't ever had much experience with women, and none since I became Jen.

"Are those boobs real?"

"Hormones."

"May I?"

I bit my lip, then nodded and she reached out and sweetly touched my breast through my top and bra. She began to fondle it and I could hardly believe it. I'd had boobs for months, but never really spent time touching them. What little I did touch them felt nothing like what Roni was doing to them. She kissed me as she explored my love mounds and though I still felt uncertain, I tried to do much the same to her.

Before I knew it, she had reached behind me and unhooked my bra, then snuck her hands back around to touch my titties under my bra. She quickly pulled off my top and my bra so she could easily touch my mammaries directly. She leaned me back against the sofa and brought her lips down to my right breast. She didn't attack the nipple but spent quite a while kissing every part of it before reaching the nipple.

She first had a long lick up the nipple, which sent chills through my body. Then she closed her lips on that nipple, sucking it and pulling away until it popped from her lips. I gasped and squirmed as Roni did that several more times. Then she lightly bit the nipple which made me moan. She bit it a few more times before mixing up kissing, licking, sucking, and biting my breast.

She paused, which made me think she might be done, and that was disappointing. Instead, she moved to the other boob and repeated the whole thing with that one. I don't know how long she spent on my titties, but it felt like it could never be too long. Before long I had what I later realized was my first female orgasm.

It took me a couple of minutes to recover, and by the time I did, Roni had taken off her top and bra. I had touched a few girls before, though that was as John, and that was always over their clothes. Now I had her breasts right in front of me and she moved forward, lowering one lovely mammary to my waiting lips.

I tried to do much the same to her boob as she had done to mine, while also reaching up and caressing the other one. I don't know if I was ever breast fed, but I felt like I was trying to suckle at Roni's tit. I also kissed and licked around it but really enjoyed taking the nipple in my mouth and sucking on it. Nothing came out and that was fine but it was the feel of sucking on it that gave a thrill.

I spent a long time on that love mound before she pulled it away from me and presented me with its partner. I gave it all the attention I'd given its mate and I could hear her moans as I did my best to pleasure her. This was so wonderful that I almost wondered if I was dreaming. If I was dreaming, then I never wanted to wake up.

I felt like I could spend the rest of my life just kissing and sucking on her breasts, and was disappointed when she rolled off me. We had been on the sofa and she stood and drew me to my feet and led me into my own bedroom. Once there, she doffed her jeans and panties and lay on my bed, beckoning me to join her.

I immediately crawled onto the bed and she guided me down between her legs. She had a sweet little pussy, with a small tuft of hair above it. She gently guided my head to her nether lips and I could smell her sweet musky aroma and wanted nothing more than to get as much of that as I could. I leaned forward and licked straight up the center of her slit.

"Do that again, and keep doing it. Harder even."

I was more than happy to accommodate her and began to lick her cunt, getting my tongue deeper in her with each lick. I'm still not quite sure how to describe her flavor, but it was pleasant and not like anything else I'd ever tasted. As I licked a nub gradually appeared at the top of her slit -- her clit as I learned. I made sure to lick it and her moans increased.

She began to pump her hips and at first, it was all I could do to keep from being bucked off. Then she wrapped her legs around my shoulders and held me in place as I worshipped her sweetness. As she moved her hips, my hands grabbed her ass and began to knead her buttocks. All this was almost beyond my ken as she came to an climax than made her shriek with pleasure.

She unwrapped her legs from my shoulders and pulled me up to kiss me and I sure she could taste herself on my lips. After a while, she rolled me off and unzipped my skirt. She lifted on my hips and I raised them from the bed. She pulled of my skirt and panties in one smooth movement. My cock was about as hard as I ever remember it being, and stood straight up.

She took the head of my prick in her mouth and sucked on it. Then she moved back up my body and guided my cock into her steaming jungle. I'd never had my dick in anyone ever before and the feel of it sliding into her depths was almost enough to make me cum, just in itself. I knew I wanted this to last as long as I could so I tried to focus on anything other than the feel of her walls enveloping me.

She kept it slow, though I suppose I'd have almost frantically fucked her if I could, but she was driving this. She had her upper body raised up on her arms which left her breasts open, so I reached up to touch them. She moaned but still kept her slow steady pace. She'd pull back until I was nearly out of her then push until our pubic hair joined.

I realized that if I lifted up slightly, I could not only touch her boobs, I could suck on them. I began to suck on one nipple as she steadily pistoned my cock deeply into her wonderful pussy. I was lost in the ecstasy of the greatest pleasure of my life. I could feel my orgasm starting to build as her love tunnel tightened on my prick, pushing me over the edge.

I grabbed her ass, pulling her tight to me as my balls emptied themselves into her. She slumped down on me panting and caught up in the throes of her own pleasure. I felt her breasts rubbing against my own and that added another level to our respective raptures. As the last few spurts of seed went in her, we both seemed to return to this world.

Roni began to kiss me as though our very lives depended on those kisses. She grabbed my head and held it tight as she seemed almost to devour me. I don't know how long that went on, but eventually she ratcheted down to a few small tender kisses before rolling off to lie beside me in bed. She was on her side facing me and I rolled onto my side facing her. She reached out and stroked my face, and I leaned in and kissed her.

"That was wonderful, Roni. I've never felt anything like it."

"Was that your first time?"

"I hope that's okay."

"Not bad for a first time."

"I hope that's not the only time."

"You want more than just tonight?"

"Absolutely."

"Then there has to be something more to it than just fucking."

"You mean like I'd be your girlfriend and you'd be mine?"

"Exactly."

"I'd like that."

"I could spend the night here if that's okay."

"It's more than okay." I stopped and thought for a moment. "I didn't think to ask, but are you on birth control. I have low sperm counts but there's still sperm there."

"We're safe. I've been with guys before, though you're my first girl with a dick."

"You're my first girl, but I wouldn't mind if you were my only girl."

"That's getting a little ahead of ourselves, Jen. Let's take it a bit slower."

"If we have to."

"It's late, we need some sleep. Turn over and let me spoon you."

I was the little spoon to her big spoon. She pulled me tight and I felt her boobs pressing into my back. She reached over to hold one of my boobs and I felt so relaxed and fulfilled. We quickly fell asleep.

.........................................................................................

In the morning, we had a little more fun before showering together and going to our respective classes. We met back at my apartment after school and spent some time studying and doing assignments before going to bed and making love again. Roni lived in a dorm which was far less convenient for us to be together, so very quickly, she effectively moved in with me.

The semester ended and we decided to get summer jobs and stay together in the apartment. My mother came to visit over the summer. I think she was reassured that I was in a relationship with a woman, though she at first wondered if Roni was like me. My father still knows nothing and my mother is still unhappy that I've become Jen.

I am almost desperately in love with Roni, though she is not quite as committed as I am. I can't be sure this will be forever, but I for now, I am happy where my journey has taken me. I am Jen and that is truly what I want to be.

jackie_em
jackie_em
1,560 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
12 Comments
CharletteCharletteover 1 year ago

So long as you keep in mind that this is a fictional story it is a pretty good read.

Kind of weird in a few places, but hey, it is a story.

I am sure the author could take it into another full length writing which would likely have all the thrills, heartbreak, drama and impossible situations that this one has.

I guess we wait to see !

thank you Jackie .

GrrrreatImaginationGrrrreatImaginationabout 2 years ago

Metroalma made an excellent observation. Whatever the back-story may be, this was a well constructed tale with depth of emotion, tension, exploration, and personal growth. I was surprised Jen/John wasn't required to see a psychotherapist, but fiction is fiction.

AnonymousAnonymousover 2 years ago

You created a beautiful and emotional story that was a joy to read. I did wonder about why the father wanted to get rid of his daughters things so adamantly and along with her mother stating that it would kill him if he found out what was going on with his son. I also found it unusual that nobody thought to wonder what happened to Jens brother and none of her friends ever wondered how she was in school after her funeral? I still hope you continue with this storyline. It is a great topic and I would really appreciate seeing how this plays out. Thanks for posting it

metroalmametroalmaover 2 years ago

"If you can slide so easily into someone else's life, did you have one to begin with?" Not a criticism, more a tag line for a great thoughtful story.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Homecoming Queen A high schooler helps a friend who doesn't have a date.in Transgender & Crossdressers
Secrets and Surrender High school can be lonely, but shared secrets can help.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
Better as Riley Ch. 01 Ryan discovers everything is more fun as Riley.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
More Stories