Jessica

This huge change strained the relationship that we had, and my girlfriend and I ended up breaking up. We remained friends but couldn't make it work romantically.

To try to compensate for completely upending my life, the company very quietly worked out a high-seven-figure settlement and arranged for me to get a new apartment and an entirely new wardrobe. My ex-girlfriend helped me learn how to walk, talk, and act like a woman. It took several years for me to have any confidence in myself but it gradually developed.

But they were lonely years. I ended up discovering how much I enjoyed bondage and amassed quite a collection of toys, restraints, plugs, and the like. But I usually only used them on myself and it wasn't satisfying ultimately since I was terrified of self-bondage going wrong and someone finding me dead after a week because of some miscalculation that I had made.

So I turned to the Internet. There were an awful lot of guys who wanted to meet up with me but I was only interested in women. Finding one who would even talk with me took a long time of waiting and talking on several different dating sites.

The first time that I met someone as Jessica I was terrified. Her name was Julie and we had talked for quite a bit online. I didn't go into how I had become who I was then but she sympathized with how difficult it could be for members of the trans community, but fortunately for me the nanobots had done a lot of what was normally only the result of a lot of very expensive and risky surgeries. Once I had learned how to behave like a woman, unless they saw me without any clothes, nobody mistook me for anything but a naturally born woman.

Julie and I had agreed to meet in public at a local place for coffee. I barely was able to order my coffee when I showed up because I was so nervous. What would she say? How would this go? I had never been involved with anyone since I had become a woman (mostly).

I had arrived first. I took an inordinate amount of time getting ready, trying to make sure that I was going to make a good first impression. I settled on a simple knee-length blue skirt, low heels, and a white blouse. Just a little bit of cleavage showing, I kept it tasteful, as I did with my makeup. Just enough to bring out and enhance slightly the natural features of my new face.

My hand was shaking as I brought my cup to my lips to take a sip when Julie walked in. She was pretty in a girl-next-door kind of way. In my previous life I would have given her a "7". She was a little shorter than I was but in good shape, with dark brown hair that she kept short, deep brown eyes, and a nice rear end. My hips were actually wider than hers!

I felt like I was going to throw up. I got ready to wave to her but she spotted me and waved with a smile. She got her coffee and walked over. "Jessica?"

"Yes. Julie?" I stammered.

She smiled with a warmth I'll never forget. "That's me. It's so nice to meet you!" she said.

"It—it's nice to meet you, too," I stumbled. Julie sat across from me and gently placed her hand on mine.

She looked me in the eye. "It's okay. We're just here to talk and I promise that I don't bite, Jess."

I swallowed. "Thank you. This is just the first time that I've...met someone...in a while," I tried to explain.

She ended up helping to quell my nervousness and we sat for two hours, getting to know each other. Julie worked as a research librarian at the university in town, had grown up in the Midwest, was one of three kids, and was still on good terms with her family. She was bisexual and wanted to explore her feelings toward women. She was very curious about me, since my listing on the site we used to meet showed that I was transgendered.

I glossed over the part about it being forced and technology gone wrong, etc., but I told her how I had a different job but still in I.T. since I had transitioned and that I had received an inheritance from a distant family member to explain how I was able to afford my (rather nice, I thought) car.

We parted on very good terms and agreed to meet up again. The next time we met, at the same coffee shop, was even better. I was more relaxed and able to accept that Julie wasn't going to shun me for who I was. We learned more about each other, our likes and dislikes, and it turned out that we had quite a lot in common. Both of us enjoyed many of the same kinds of music, food, and other entertainment.

Julie and I agreed on a place and a time to go on a date. Nothing too fancy, but not McDonald's, either. Halfway through dinner I realized that I had a crush on Julie. I was finally getting comfortable around someone who didn't know about what had happened to me for the first time. It felt wonderful.

Once we finished with dinner Julie looked at me while we waited for the check to arrive. She had paid, wisely sensing that I would appreciate one less thing to worry about. "I'm having a lot of fun with you, Jess. Want to come back to my place for a drink?"

My stomach lurched and I felt my cock twitch. Which was uncomfortable since it was tucked between my legs. It was never a comfortable arrangement but it was the best that I could do. There was no way I was having SRS but also no way I was ever going to be a man again. I was even more nervous now that I had been waiting for her to show up the first time that we met. I swallowed and answered, "I'd love to." Which was the truth, after all.

She beamed. "Great," Julie said, lightly resting her hand on mine. My stomach jumped again. It felt fantastic.

On the drive back to her place she didn't say anything except for giving me directions. Before I knew it we were in her living room, each of us with a glass of red wine. It was pretty good, I thought, my eye catching the lipstick that I left on the glass. I had stopped noticing things like that a while before but for some reason it really struck home that I was actually a woman about to (hopefully!) get intimate with another woman.

We made a little small talk on the couch until there was a lull. Julie's intoxicating brown eyes locked with mine. "I'm really attracted to you, Jess. Not because of anything physical that makes you rare, just...you're a lot of fun to talk with." Her hand was on mine again. And so my mouth was disabled. It was also dry as a desert.

I swallowed hard and finally managed to say, "I really like you, too." All that I could focus on was how nice it felt to have her soft skin against mine, covering my red-painted fingernails.

She scooted closer to me, never taking her eyes off of mine. I swallowed again, my heart thundering. Julie's face leaned in toward mine and our lips met. It was the softest, most delicate kiss I had ever had. It was completely kissing a woman now that I was one! My nipples stiffened in my bra as the kiss went on and on. My crotch was starting to get uncomfortable, too, since my nipples weren't the only things getting stiff.

"Wow," was all that I could manage when the kiss broke.

Julie had a furtive grin on her face when she replied, "Yeah. Are you sure that this is your first time?"

I chuckled. "I had kissed a few times before I transitioned, you know," was my answer.

"It seems like the practice got you pretty good at it," she said and leaned in for more. This second kiss was not the tender first kiss. She came at me with real passion this time, and I moaned softly into her mouth. Her tongue found mine and they danced, while her soft lips and mine writhed against each other. We separated after an even longer time, during which her hands managed to find one of my boobs which precipitated another soft moan from me. All that I had managed to do was stroke the soft skin on her back under her shirt.

"I, um...I really want to see where this goes," she told me. "But I completely understand if you want to take it slow!" she added with haste. "I don't want you to feel pressured, not at all, but I want you to know if you feel like going further I am 100% in agreement. You're a fantastic kisser and you're pretty hot already...but you also have more to offer," she explained.

My poor restrained dick was screaming at me to get on with this but I was still apprehensive. What if it turned out that she didn't realize that she wasn't as attracted to me as she thought she was? What if...? I took a deep breath before deciding to say, "Fuck it!"

I'd been quiet for several seconds and realized that she was waiting for me to say something. I was nervous as hell but she must have been, too. After another deep breath, I stood up, drained my wine glass, and gave her the best smile my anxiousness would allow. "Where's the bedroom?"

Julie squealed with delight, jumping up and hugging me tight, then kissing me with even more passion than before. "This way," she cried, grabbing my hand and practically dragging me behind her.

I think her shirt hit the floor before I had even crossed the threshold. Her pants followed quickly and I got a good look at her body. Even with her pretty, matching bra and panties, she had a great one. Her skin was flawless and while I did still have wider hips, hers were nothing to dismiss! They tapered up to a small waist, a stomach that was flat but not without being feminine, and bigger tits than I had thought. Her legs were shapely, maybe not as muscular as I might prefer, still were toned and strong.

She smiled at me, a delightful soft and kind smile. "You should keep on whatever you feel comfortable with," she reassured. "I want you to feel comfortable, Jess."

I choked up a little and hugged her shorter form tight. "Thank you for being so sweet and understanding about me, Julie. I can't explain how much I appreciate it," I whispered.

She hugged me back and said, "I don't want to ruin your first time and I really mean it, I want you to be comfortable."

I looked down at her. "Thank you," was all that I said before I stepped out of my low heels and reached behind my body to unzip my knee-length skirt, letting it drop into a pool around my feet. My underwear was very feminine but underneath it I was still wearing my gaff, which was doing extra duty to restrain the erection that was trying very hard to appear. I looked Julie in the face as I unbuttoned my blouse and pulled it off, revealing my bra to her as well. Mine were purple and not black like hers, and mine were satiny whereas hers were lacy.

I looked up at her and gave her a nervous smile. "Well...here I am."

She looked me up and down and gave a wolf whistle. Which was exactly what I needed, and it was so unexpected I couldn't help but guffaw, doubling over. By the time I settled down I was near tears. "What's so funny?" she asked with a quizzical smile.

"I'm sorry, but I was so nervous that you wouldn't like what you see and that was so unexpected, it just struck me as really funny," I clarified. "I'm glad that you like what you see," I told her, giving her a terrible approximation of a pirouette.

Now it was her turn to laugh. I giggled in response, and closed the distance between us. I got serious and said as I hugged her again, "You do like what you see, right?"

I didn't get words as an answer. Instead Julie kissed me with even more fervor than the last time. And now it was really time to get this damn gaff off!

I broke the kiss. "I do have one more thing to take care of, I'll be right back," I said, then hurried to the bathroom. As I closed the door I started wondering if I should put my panties back on or if I should just go all the way and go back out to her naked. For the second time in half an hour I found myself saying, "Fuck it!" I peeled my panties off and tackled the gaff as soon as I could. It took a little work but it was such a relief to have it off. My enhanced girl cock was most of the way to erect, and then I had a change of heart. I wanted her to have something to unwrap. Bra still on, I put my panties back on, and stuffed my member off to the side, making quite an obvious bulge.

One more deep breath and I opened the door. Julie had sat down on the edge of her bed and looked up as I turned the light off. "Wow. Where were you hiding that?"

I couldn't help but chuckle. "I wear a gaff to keep from...arousing suspicion," I said, raising an eyebrow.

She giggled. "By the looks of things, you're pretty well aroused already!"

"What can I say? I'm really attracted to you, too."

Another of those super-sweet smiles. "Come here."

I walked over to her, standing in front of her. She didn't stand, she just took my hand and smiled up at me. I couldn't help but return it. Her other hand was covering my hips and side with soft caresses and light touches that were only making me harder. She released my hand and both of hers got into the action. It felt fantastic. I closed my eyes and just enjoyed the feeling of her stroking my skin, and smiled when I felt her following her hands' roaming around with light kisses.

"That feels wonderful," I breathed. She just murmured an approving sound and continued.

A few seconds later I heard, "But I'll bet this'll feel better," as her small hands pulled the front of my panties out and away to the side, freeing my eager dick. No sooner had she pulled that move, I gave out a husky moan, feeling her grab my foreskin, slide it back, and replace its presence covering my sensitive head with her hot, wet mouth.

"Oh, god, Julie..." I groaned. Once again I basically got an approving sound while her tongue danced around my head. "Fuck, that's good, baby!" I opened my eyes when I felt her begin to take more of me into her mouth, her hand an inch farther down my shaft, pulling my skin up and down in time with the movement of her head.

My legs were getting weak. "Can I lay down if you want to keep going, please? I might fall over if not."

Julie released me and grinned. "I definitely do want to keep going but we can't have you falling over and getting hurt." She patted the bed. "Hop on up!"

"Thanks," I said, removing my panties as I did. No use keeping the wrapping paper on Christmas morning once the gifts are out, is there?

"Here, let's get rid of this, too," she said, reaching behind my back before I could lay down. She had it off in a flash, tossing it over with the rest of my clothes on the floor. "Jess, you're gorgeous. Your boobs are so beautiful."

I blushed. "Um...thank you. I'd say the same if I could see more of yours, I bet."

"That's right, this isn't very fair now, is it?" And with that her panties and bra were gone in seconds.

"Yours are beautiful, too. Like the rest of your body," I told her. It was true. She was a little shorter than me at about five-foot-four, with full, perky breasts that while smaller than mine were still fantastic with little pink areolae topped by pencil eraser-sized nipples. Her butt was tight and muscular, like a runner's, and her legs were a little more toned than I had realized. I put in a fair number of miles running every week, so mine are more muscular while staying toned and feminine (thanks, nanobots!) but again, Julie's were great in their own way.

My reverie was broken when she said, "Now, where were we?" as she laid down next to me and took my length even deeper into her mouth than before, working from the head down to about halfway down. I hadn't had any sex in so long I had almost forgotten how good a well-executed blowjob feels. She wasn't just bobbing her head up and down, either. There were slurping sounds coming from her as she applied a heavenly amount of suction while at the same time I felt her tongue swirling around my entire shaft and head.

I moaned again. "That's sooooo good, honey," I told her. I still had enough presence of mind to realize that her wonderful body was right next to me so I started exploring. I ran my hands up her smooth legs, over her hip, up her side, and gently cupped her right breast. I could feel her nipple poking into my palm as I massaged it, getting a soft moan of approval in return for my efforts. I began moving back down after that, tracing down her belly to between her legs. Once she realized what I was doing she spread them for me without changing her technique at all, still wrapping my girl dick in ecstasy. I paused and closed my eyes for a few seconds, just reveling in the feeling of her sucking on me and the softness of her skin. I opened them up and moved down her body, finding that her crotch was devoid of any hair, just like mine. It felt like she either had had it waxed within the last day or two or she had shaved less than a few hours ago, it was so smooth. And soft.

I drifted a little lower and my fingertips ran into slippery moisture, hearing a more enthusiastic moan. I explored her little pussy and found that her labia were very small but she was incredibly wet. "Mmmmmph!" she groaned when I found her pleasure button and began to run delicate, slow circles around it. "Mmm-hmmm..." she continued, still sucking my cock like it was her job and she was looking for a raise.

"I want to taste you, too," I whispered. She did have to stop to do it, but without removing me from her lovely-feeling mouth, Julie re-positioned herself so that she was on top of me with her delicate flower right in my face. I could feel her tits on my belly.

"Hello, gorgeous," I said in greeting to her pussy. I started to kiss around the edges, just inhaling her scent and tasting her skin. It was delicious. I moved inward, kissing and nibbling her adorable lips, first the outer and then the inner ones. She groaned when I lapped her from her top to her bottom, scooping out some of her arousal as I went. "You're delicious, too," I told her. "I can't wait to make you come."

Julie groaned around my erection, which felt like heaven. I dove in. I stuck my tongue as deep inside her as I could, working around, and had to work to get in. She was really tight. I kept exploring but settled on simply tracing circles around her hard little nub. She started to twitch a little and it was a good thing: I was starting to succumb to her ministrations. "Oh, fuck, baby," I moaned before getting right back to work.

The timing was serendipitous. She started to tremble just as I felt myself getting close. "I'm getting close, baby...if you don't stop you're going to make me cum," I warned and went back to licking her. All I got for a response was a lusty groan. Fair enough, then. I sped up on her pussy, trying to get it so that we both came at the same time, and it worked. "Oh, fuck!" I cried as I felt my scrotum tighten up. She was moaning as she kept up her slightly more irregular movement, then just as I wrapped my arms around her waist to pull her down to my face before I exploded, she screamed around my cock and her hips started bucking. The vibration from her voice sent me over the edge and I cried out into her cunt, trying to keep her orgasm going as long as I could.

As an aside, I could have mentioned earlier but one of the biggest things I had a hard time getting used to after my forced transition was hearing my new, female voice cry out when I had an orgasm. I didn't feel any of that this time.

I had to stop because she was trying the same thing. "Baby, you have to stop!" I told her.

She pulled off of me with a gasp and replied, "Oh, so do you! I'm way too sensitive after that!"

We untangled our bodies and laid down next to each other, panting but happy and kissing passionately.

When we finally stopped, Julie cupped my face in her hands and looked deep into my eyes. "That was some of the hottest sex I have ever had. If you've been out of the game, the world has been missing out, Jessica! Holy shit! I'm still shaking!" she giggled.

"Thank you for that, it's been an awful long time...and you're a master at that!" I answered.

She paused for a few moments, appearing to be thinking. "What's up?" I asked, the afterglow from receiving a fantastic blowjob washing away any inhibitions that I had had at the beginning of the evening. After all, I had just had my face buried in her cunt.