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My Unwanted Transition 14


I still can’t believe Alice got Skylar and Jen to agree to her plan. My anxious thoughts of Alice with Skylar are still being balanced out by getting a chance with Jen again. Even though it only took a couple days to iron out the plans, it feels like an eternity. My excitement and worry are wrapped up in one as the hours of the day pass slowly, closing in on the time for me to see Jen.

When the time comes, Alice and I kiss, pressing into each other for the last time before sharing a different partner for the night. I’ll be going to Jen’s place, and Skylar will be coming here. I leave and make my way to her house with the guilt of our kiss still weighing on my mind. I lied to Alice about it, then that lie spiraled into a chance to have sex with Jen again. It doesn’t feel right, yet the arousal causing my cock to be solid in my pants drives me forward.

Jen welcomes me in, my best friend for years, but right now, I can only see her as a sexy woman. If she offered, I’d have sex with her right now. Instead, we follow our plan and play some games while ordering food, just like our old hang out times. The games distract me enough to keep from having an erection the entire evening. Hours tick by, and so do the games until we’ve played nearly every multiplayer game we have.

“What’s next?” I ask, sitting up to stretch.

“Why did you kiss me?” She asks.

“Um,” I respond, then pause. “Seeing you be so sexual with Skylar reminded me of how we used to have fun. I always think we probably could’ve had the best of both worlds if we dated each other.”

“Maybe,” she says. “It could have ruined our friendship, too, though.”

“I guess that’s true too,” I say.

“How do you feel about me now?” She asks.

“That’s hard to answer,” I say, sighing.

“Right now, how do you feel about me, like as we sit here?” she asks.

“I feel like you turn me on immensely. I also feel like we can just play games all night.”

“Hm. Well, why don’t you play something, and I’ll be back,” she says, the tone of her voice making me worry a little like I said something wrong.

I watch Jenny go upstairs, then find a new game to play. It’s a single-player game, but it’s one we both like and usually take turns on. I see Jenny come back down almost twenty minutes later. She’s wearing a dress, stockings, and heels. She walks back over to me, her hair flowing down instead of being tied up. I feel my cock rush to attention as she stands a few feet away.

“Keep playing,” she says.

“Huh?” I say, confused.

She drops down in front of me, and my heart speeds up. I can’t imagine she’s about to give me a blowjob. Her hands adamantly undo my pants until my cock is in the open. Again, she tells me to play, so I unpause and make an attempt while her mouth closes over my dick. It isn’t easy to concentrate on the game with the feel of her sucking me so good. Her head moves up and down in my lap, and wet little noises are produced by her lips. I can’t believe how into it she is.

“Are we supposed to record?” I ask.

“We will,” she pauses long enough to answer.

Something about her answer turns me on even more. Her mouth continues to pull up and down all seven inches of my cock, and the way she can take it all is phenomenal. She isn’t the same brand new girl from when we first experimented, but rather a much-experienced woman now. I try to play the game in front of me, but she goes faster, her throat pushing moans out, each one driving me closer. Spit is spilling messily from her mouth, the motions of her tongue making it even worse.

“You’re gonna make me cum,” I warn.

Jenny doesn’t stop. She wants me to cum, and my warning only serves to encourage her. Her hand grips me, stroking with urgency while she licks the tip. The way her saliva coats my shaft makes it easy for her fingers to glide up and down. I tense up, feeling my load rushing into my cock, then it explodes into her mouth. Her lips clampdown, containing it all, waiting for me to finish before swallowing. I can’t help but wonder if she did that so we wouldn’t have to have sex.


I sit across from Alice, waiting for the check for our dinner. Besides talking in passing, we don’t know each other well, so we both thought it a good idea to spend some time together. Dinner was good, and so were our conversations so far. I learned that she works in criminal forensics, so we had quite a bit to talk about. She’s a little shorter than Jenny and smaller in the chest, too, at least from what I can tell through her top. Her hair is longer, though, and she has more curves around her hips and waist. I insist on paying the bill, even though she protests, but I’ve always been a hopeless romantic in this manner.

When we arrive at her place, she has a camera already set up in their bedroom on a tripod. It doesn’t surprise me since she comes off as a professional and calculated woman. This was her plan from the start, so it makes sense that she’d be prepared. On the other hand, I prefer sex to be less planned and robotic.

I try to slow things down using my charm and eventually get her to lie down so I can give her a massage. It’s just a basic version, no candles or oils, just her half-naked while I work her muscles. I can feel how tense her body is, probably worked up from this plan and the job's stress. She starts to relax after a few minutes, then turns over on her own. Her breasts are definitely smaller than Jenny’s, but they are very perky. She has a nipple, navel, and clit piercing, with a chain attached to her navel. I didn’t expect her to have additional piercings, but I love them.

I continue the massage, my dick now stiff in my pants. Even though Alice is quite attractive, I’m still somewhat wary of having sex with her. At the same time, I picture Andy and Jenny together right now, probably already well into their session. Although I’m not sure about being with another woman, I look forward to watching Andy and Jenny’s video.

I’ve made it down to Alice’s feet now, which are just as cute as Jenny’s. I avoid doing anything sexual to them since I don’t know how she feels about it. Instead, I kiss along her leg, moving slowly to give her a chance to stop me. When I reach her thigh, I look at her face. She has her eyes closed, and her expression is soft. I continue, making my move to her womanhood, placing light kisses upon the outer folds, again, giving her a chance to stop me.

I hear her draw a breath in as if she’s anticipating my going down on her. She has her legs spread wide, with no sign that she doesn’t want this. I move up more, then place my mouth on her, using my tongue to press her clit, which is decorated with a small ring. This is my first time going down on a girl with a clit piercing, but I like it. Alice moans, the sound much different than her talking voice. She sounds sensual and vulnerable. I remember that there’s a camera recording us, so she could be putting on a show too.

I’m eager to make her cum, wanting to see the expression on her face as she succumbs to pleasure. She moans every little while, but I adjust my technique based on her breathing. The room is quiet, so I hear each time she takes a quick breath in. She eventually brings a hand to my head as she moves her hips. The thought of her getting close excites me, making me increase my speed, my eagerness.

“Fuck! Yes!” She moans out loud.

Her fingers curl into my hair as she voices her pleasure in profanities. The way she lets her pleasure be known makes my dick throb. I want to fuck her now. The way she moans, the pleasured look on her face, and her piercings turn me on immensely. I sit up on my knees, my cock tenting my boxer shorts, and Alice lies still in the last moments of her climax. As she lies there, I take in her figure, her features more refined than Jenny’s, but I can’t explain it exactly. Jenny is absolutely gorgeous, though she lacks the small details that a natural woman has. I only notice this because Jenny is on my mind as I look at Alice.


The taste of Andy’s cum is still in my mouth as we play more games. Times like this remind me of when we were younger, staying up all night, then sleeping for two hours. We have all night tonight, and my blowjob seems to have satisfied him for a bit. I know we are supposed to record our night, but I didn’t want to ruin the moment's spontaneity. He catches me looking at him while I reminisce.

In a smooth motion, he leans in and kisses me. Our lips meet briefly before he pauses, then he begins again, only this time he’s more aggressive. As he pushes me down on the sofa, I feel the same energy in him from the party, when he kissed me in the bedroom. He claims the entirety of my mouth with his tongue, and his hand roughly tugs my dress down. His hand grabs my exposed breast, squeezing it with want.

My want rises to meet his, wanting to share what we did years ago. We’re both more experienced now, especially me. I have no qualms about being a woman or with being with a man. His movements tell me how bad he wants me, so I put a leg around him, letting him know I want it to. He moves from the kiss to my neck, biting my collar bone, then even lower to my nipple. I remember that we’re supposed to record this, but I don’t want him to stop, and my phone is out of reach.

As he moves back up, I can see his dick out, which vanishes between my legs, then I feel him enter me. I’m wet, so the only resistance he encounters are the muscles of my walls, which stretch to fit his manhood. I realize how close in size he and Skylar are, enough to give me plenty of pleasure. His hips begin to work back and forth, ramping up into quick, powerful thrusts. I wince in pain from the sudden depth he takes in me, but he doesn’t stop or slow down.

Pleasure eventually overtakes the pain, and I look back and forth from his face to where his cock is slamming my body. Our awkward position on the sofa doesn’t hinder us at all. He has me turn over on my hands and knees, guiding my hips into place with his hands. Again, he shows no mercy as he bangs me like a toy. This is precisely what I wanted; a continuation of where we left off before, when he had me in my own room.

Andy’s vigor keeps up long enough to make me cum. I turn over again, my arms and legs shaky from how intense it is. His dick is still solid, waiting for me to rest so he can continue. I need to stall a bit longer due to the warm pressure I feel in me, which I know means I’m close to squirting. Having that kind of release feels even more intimate than sex, and I only want to experience it with Skylar.

“We should start recording,” I say.

“Good idea,” Andy says. “Alice gave me a tripod to make it easier.”

Andy gets the tripod from his bag, then we go upstairs. Once the camera is recording, I get down and suck his dick some, at least giving the illusion that we’re just starting. I don’t know if we’ll end up being truthful or not later on. Maybe about how he took me on the sofa, but I feel that the blowjob was just something between us. I did that to make him feel good, to break the ice, and to show off how good I’ve gotten.

I take the top this time, starting with reverse cowgirl. It’s a fun position, but it wears me out quickly. I go for as long as I can, then I turn around on him, bouncing myself in a hard, rough manner just as he did to me. His endurance outlasts me a second time as I begin to cum again. This might be the last time we ever get to do this with each other, so I know he intends to have as much of me as he can. I want to give him as much as he wants to take.


I can’t believe how good Skylar is with his mouth and tongue. The way he massaged me, then went down on me, was amazing. From the first time I met Skylar, I had a crush on him. It wasn’t something I ever considered pursuing since I’m with Andy, and I love him very much. But Andy and Jenny have been together before, so I figured I get the best of the deal here.

Skylar takes his time, deliberate with every touch, and kiss on my body. He’s between my legs now, his hard dick brushing my stomach as we kiss. He doesn’t push inside me like I expect, another one of his attempts at teasing me and building my anticipation. I feel him pull back and press the tip against me, only to withdraw each time. My hips are lured up by him, ready and waiting to feel it. He moves forward again, this time letting his manhood claim me.

The slow start leads into a deep, carnal fucking. His eyes never leave mine as he plants his cock in my slit over and over. The way his eyes gaze on me makes me feel vulnerable, like he’s conquered me and claimed my pleasure. His hips rotate in almost a machine-like manner, driving into my body as if his stamina is endless.

He finally stops and slaps his cock against my pierced clit before standing up. As I start to move, he pulls me toward him, his arms curling around, then lifting me against his body. The way his strength handles me is incredibly arousing, then I kiss him as soon as I am able. He allows my tongue to probe his mouth while my body is lowered enough for him to penetrate me once more. I wrap my legs around him for balance, joining the cause of our mutual pleasure. He thrusts his hips up, and I force mine down.

When we both tire, he sets me down, then I turn and bend over the bed. He secures my hips in his hands, then fucks me more. His speed and urgency rise with each moment, then he groans out a warning of his imminent orgasm. I pull forward and turn, dropping to my knees, then scooting to the side so that we’re on the camera properly. I reach and stroke his dick, licking it, sucking it, anything to aid his finish. The warm heat blasts my face as he cums, covering me in his seed.

He brings a towel over for me while I clean up in the mirror and begins to assist me from behind. His free hand slides down my stomach, over the chain, and he fingers me. I’m held in place by his left arm while two of his fingers rapidly work inside me. I watch in the mirror as he continues, seeing every motion of his fingers. A sensation of pressure swirls around, building with each intrusion of his skilled digits as they remain buried in my slit. My climax builds simultaneously, then when it finally overtakes me, I feel a sudden rush of wet between my legs.

His hand pulls up, then he roughly swipes back and forth across my clit, which makes me squirt more. For several seconds, each contraction of my womanly muscles pushes more out of me. I lean over on the dresser, my legs shaking and my mind in shock. There’s no way I just did that. I’d know if my body was able to do something, and this isn’t something I can do. The erotic droplets running down the inside of my thighs are evidence to the contrary, though.

When I finally accept what happened, there’s a part of me that wants him to do it again. I turn and face him, standing on my tiptoes so we can kiss. The warm, pleasant afterglow is still present throughout my body, making me feel incredibly sensual. I kiss his lips, then his neck, his chest, then even lower. His cock is already growing erect again as I kneel down. I suck his dick until we end up in bed again, and we fuck. I try to focus on squirting, but it doesn’t happen, even though I do have another pleasant orgasm before he unloads on my stomach.

It takes a little time to clean everything up, then we finally relax in bed. I’m thoroughly satisfied, more than I thought I’d be with Skylar. Still, now that my arousal has mostly subsided, it feels strange to have him in bed with me for the night. Even so, I feel accomplished that I was able to pull this plan off. Jenny kissed my fiancé, so I fucked hers.

“I hope you feel as good as I do,” Skylar says, breaking the silence.

“Oh, I do,” I say. “Isn’t it amazing how something like Jenny kissing Andy could lead to this?”

“Mm, yeah,” he responds. “But don’t you mean how Andy kissed Jenny?”

“It was Jenny,” I say, sitting up more. “At the party, she and Andy were talking in the room, and she kissed him.”

“Jenny told me Andy started it,” he says. “One of them is lying.”

“What if both of them are?” I ask.

“What do you mean?”

“What if they did more but only admitted to a kiss?” I say. “I mean, if they’re gonna admit to a kiss, there’s no reason to lie about who started it unless they didn’t get their story straight.

“I don’t know,” he says. “I don’t really want to think about it right now.”


I watch Andy’s face as he seizes up in his climax, his cock expanding and throbbing inside as it powerfully injects semen into my body. A somewhat awkward silence takes us both as we clean up. I think back to the first time he ever finished in me and how scared I was. I remember him coming into the room the next morning, then tossing a morning-after pill at me. More memories come to mind, each one something Andy did for me that I appreciated so much.

“Maybe you should come with Alice and me on our honeymoon too,” Andy says with a laugh.

“I think fucking your best man, or woman in this case, is plenty,” I say, smiling.

“Jen,” I have to tell you something,” he says, his tone more serious now.

“What is it?” I ask.

“At my party, I put in a lot of money to increase the chance of seeing you naked,” he says.

“Thank you for all the money, then,” I say, smirking.

“You aren’t mad at me?”

“No, we were all just having fun,” I say. “Honestly, putting on a show in front of everyone like that was a huge turn on.”

“It was definitely a good show,” he says, then goes silent for a minute. “Can I tell you one more thing?”

“Of course.”

“Well,” he starts. “I think I’m still more attracted to you than Alice.”

“Oh, well, I think you two are great with each other,” I say. “And, I would never hurt Skylar again.”

“I know, I’m not asking you to run away with me or anything; I just wanted to get it off my chest.”

“I understand,” I say. “I still have deep feelings for you too, and tonight made it worse than better, I think.”


We arrive at Alice and Andy’s wedding, which reminds me that we still need to plan ours. As we sit in the car, I look at Jenny, remembering what Alice said about Jenny kissing Andy. It’s something I should’ve asked about already, but I don’t want it to seem like I don’t trust her. We’re about to attend the wedding of two people we’ve had sex with, so I’d rather the air be clear.

“Um, Jen,” I say.

“Yes, love?” She responds—her chosen word making me feel worse about asking now.

“Alice said something back when we did the switch thing,” I start. “Apparently, Andy told her that you kissed him first.”

“I’m sure he did,” she says, producing a small laugh and smile. “He definitely kissed me first, and like I said then, I didn’t stop him, not at first anyway.”

“I figured,” I say, relieved that she didn’t get upset.

The ceremony doesn’t contain many people, just some close family and friends from both sides. Jenny is wearing a female tuxedo, which makes her look ridiculously sexy, but she’s busy with her part of the wedding. Eventually, the main event starts, the music plays, and Alice is escorted by her father. I watch Alice as she walks the aisle, also looking beautiful. Jenny is now standing close to Andy, and I look at her, picturing her in a wedding dress, walking in Alice’s place.

After the vows and rings are exchanged, most of the guests head to the reception, including Jenny and me. There are drinks, music, and dancing, and in-between that, Jenny gives a toast and a small speech about Andy. I bring Jenny out to dance when the music starts up again, then we sway through a few songs. We switch partners for a couple after that, so I dance with Alice and Andy and Jenny dance together.

“We haven’t been this close since you were between my legs,” Alice says.

“I suppose not,” I respond, caught off guard.

“Don’t tell me you have regrets,” she says.

“No, I just wasn’t expecting that to be the first topic,” I say.

“Don’t be such a stiff,” she says.

Alice isn’t afraid to get close or to press against me as the dance continues. I have a full erection by the time I’m back with Jenny. Eventually, the festivities trail off, we say our goodbyes, and the remaining few make their exits. As soon as we get in the car, Jenny removes her high heels, her feet probably tired and achy from wearing them all day. I start to drive us home, and Jenny reaches over to touch my crotch as soon as we depart. Her hand works my pants and zipper until she’s able to get fingers around my cock. It only takes a few moments before I’m completely hard and finding myself distracted by her hand stroking me.

Jenny leans over in the seat, her hand holding my cock as she takes it in her mouth. We’re an hour away from home, so there’s no way for me to rush back. Instead, I try to focus on driving with her head bobbing up and down in my lap.

“Pullover somewhere,” she pauses to say.

I start looking for a place to stop, anywhere at this point. Jenny continues to suck my dick energetically, and nothing is stopping her from making me blow my load if I don’t find a place to park. I see an old store that looks out of business just up the street, so I pull into the lot. There’s a spot alongside the building to park in, which gives good cover except from the point we enter. Jenny sits up, then gives me a devious smirk, one that leaves me eager to see what’s on her mind.

To my surprise, Jenny begins removing her clothes, though it is an expensive, rented tuxedo, so we definitely don’t want to ruin it. She sets the top and pants on the dashboard, then we move to the backseat. I pull her panties off before working my way between her legs, trying to make do with the little room we have. Her pussy is wet and hot as I finally slide my cock inside her. The small area of the back makes it difficult to build a rhythm, leaving us wanting more.

“Wait, let me up,” she says. I can hear the frustration in her voice.

She steps out of the car wearing nothing but her bra, stockings, and high heels. I follow her to the hood, which is facing away from the street. The horniness driving her to want to fuck right here winds me up like never before. As soon as we reach the front, I bend her over, then slam my dick into her cunt with all of my pent up lust. Her hands lay firm against the hood, trying to balance my aggressive thrusting. My hands hold her hips, pulling her backward every time I plunge into her waiting slit.

The lust drives an idea into my head, making me act on it without further thought. I unhook Jenny’s bra, then pull her arms until she’s standing with her back to my chest. I hold her in place, exposing her sizeable, perky tits to the outside world. She doesn’t protest or resist but just stands there, letting me display her.


I look toward the street, feeling the outside air swirl around my bare breasts. Each time a car drives by is another person’s opportunity to see me, to see my nudity. I try to look at the occupants, wanting to know if they take a peek, needing them to. Skylar pushes me back down so he can fuck me more. Doing this so openly outside has me incredibly turned on, so much that I’m on the edge of my orgasm. He pulls me up again as another car stops for the light.

This car has the windows down, so I can clearly see the driver. He appears to be an older guy, maybe in his forties. My excitement grows even more as he turns his head, his eyes locking on me, and I know for sure when he does a double-take. I start to cum, unable to hold back, my body shivering in climatic bliss. The driver holds his phone up, likely taking a picture, or even a video, which is such a massive risk, but it makes me so fucking horny. My heightened arousal is enough to make me instantly cum a second time.

Skylar grips his fingers into me when he finishes, grunting, and his cock swelling in me as it unloads a torrent of his seed. I turn to face him when he pulls out, kissing him, then giving him a punch in the arm.

“Why would you do that?” I ask, trying to regain some of my self decency.

“I didn’t hear you say stop,” he counters. “You want that guy to go home and jerk off to you, and you know it.” I feel a heat blush rush into my cheeks. “Well, do you?” He asks when I don’t say anything.

“Yeah,” I say softly.

“Yeah, what?” He asks again.

“I want him to jerk to me,” I say, louder, and somehow it helps me accept it too.

The ride home is quiet as we both wind down from the wedding and our escapade in the parking lot. We take a shower when we finally make it home, then settle into bed for a relaxing evening of watching movies. Alice and Andy’s wedding gets us talking about our own, which leads to an exchange of ideas. Luckily, we both seem to want mostly the same thing, a small wedding with friends and family.

“What about having kids of our own?” Skylar asks.

His question gives me a sharp reminder of my transformation. Having kids means I’ll be the one pregnant and eventually giving birth. I’ve been assured that my body is capable of such. Skylar placing his hand on my stomach snaps me out of the daze.

“Do you like that idea?” He asks again. “Having a couple of kids?”

“I’ve thought about having kids, but it isn’t something I’ve given much thought as, well, the way I am now,” I explain.

“I understand,” he says. “I wouldn’t be sure if I was in your position either,” he adds, rubbing my stomach, then giving me a kiss. I can tell he’s worried about me saying no.

“We can at least make an appointment to see my doctor. This way, we’ll know if it’s safe for me,” I say.

“Are you sure?” He asks.

“Yes, I’m very sure,” I say, smiling.


We both take off work for the appointment, and I drive her there. Jenny is used to coming to this facility. It’s where she was born again as a woman and where the only doctors are that know her inside and out. I can tell they’re happy to see her, like she’s a prize experiment. Due to the nature of our visit, the exam is very intimate.

There’s a round of x-rays, then an ultrasound before she has to lie down with her legs spread. The doctor inserts different tools into her body, opening her vagina wide. A liquid is then injected into her, which is supposed to flow into her reproductive organs. The machine sends the video images to the screen, which pops up with a diagram of her tubes and ovaries. She grabs my hand with her fingers, so I hold her hand in mine as we watch.

“Everything appears to be in working order,” the doctor says. “Please keep in touch should you become pregnant so we can monitor you for any irregularities. You are the first for all of this, Jenny, so it’s a new world for us.”


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