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My Unwanted Transition 12


My plans to see Jenny soon were foiled by increased workloads at my job. A sudden spike in cases put most of us into working overtime. When I did manage to grab a free moment, I spoke with her on the phone. She told me about her visit to see some others that were going through the same thing she had. I could tell she was happy about the visit.

My workload broke a couple of weeks later, and I asked Jenny out on a date, but instead, she invited me to her place. I hurried home and freshened myself up, giving my face a shave, then taking a shower to wash the grime of the day away. It wasn’t often that I stopped to decide what to wear, but looking good for Jenny was important. I put on a soft, button-up shirt and picked out a pair of fashionable jeans. To wrap things up, I dabbed on a little cologne, then did a final check before departing.

Jenny greeted me at the door, wearing a black dress. It hugged every curve of her body perfectly, the bottom just overlapping with her stockings, and those gripped her soft, strong legs all the way down to where her slender feet tucked into heels. I put my arms around her body, drawing her closer, so I could kiss her lips. If it wasn’t for the smell of the food she obviously prepared for us, I had the mind to fuck her right in the doorway.

“Everything looks delicious,” I say as we sit. “Did you cook all of this?”

“With the help of Google, yeah,” she answers and smirks.

“Anyone can find a recipe online, but that doesn’t make them a good cook,” I say, then take a bite. It’s delicious. “And, this is obviously made by a good cook,” I add. “Or maybe I’m just saying that so I don’t ruin my chance at sex tonight,” I say again, laughing.

“I’m glad you like it,” she says, ignoring the joke at first. “I don’t think you have to worry about ruining that,” she adds, her eyes looking at mine, appearing to contain the same lust I have for her.

Halfway through dinner, I feel a warm touch slide up to my crotch. It takes me a moment to realize it’s Jenny’s stockinged foot. She doesn’t say anything and continues to eat normally. I feel her toes press forward, seeking until she can feel my cock start to grow in my pants. Once she finds it, her attention focuses there, her foot rubbing up and down. My appetite for food is quickly replaced by a hunger for her. Without thinking, I reach down and unzip my jeans so my dick can push through the opening and into the free air. Still, Jenny isn’t dissuaded nor distracted. I feel the softness of her stockings touch my bare cock now.

“Oh, hi, Skylar,” I hear a voice chime in. Leslie’s voice. “I won’t disturb you guys, just getting a drink.”

Leslie passes the table and walks into the kitchen, but Jenny doesn’t stop. She continues to press and move up and down, doing anything she thinks will make me feel good. Leslie gets her drink then stops by the table as she comes back. Jenny still continues.

“The food looks awesome; I hope ya’ll leave some leftovers,” Leslie says.

“I’m sure there will be,” Jenny responds, her foot still teasing away at me.

When Leslie finally heads back upstairs, I feel Jenny pull her foot away, leaving me at full mast. She stands now, then walks around the table toward me. She places one hand on my shoulder for balance and sits down on my lap with one leg on either side of me.

“Leslie’s just upstairs,” I say, more as a caution to Jenny and not a protest.

“I don’t care,” she says back.

If she doesn’t, then neither do I, and our lips meet. Her breasts touch my chest, and I notice they aren’t as full as before. It then dawns on me that they were probably swollen while she was on her period. That’s something I remembered from sex ed. Bigger or not, I still love them. When she starts rotating her hips against me, it’s the last straw. I push my plate out of the way, then lift her onto the table. As I spread her legs open, she lies back, then I quickly push my jeans down just enough to free my cock.

Jenny lets out a moan as I shove myself inside her. She’s wet, warm, and tight around my throbbing erection. Her legs hook around me, spurring me to continue, and I do. I put my hands on her shoulders, holding her against the table, and slam my hips forward to drive dick into her waiting body. Her tight, silky walls stretch to accept me, and she moans again. When I pull out, I feel her pussy grip my cock like it doesn’t want me to leave. Again, then again, I hammer my hips into her. Her eyes, the pleasure in her face, her scent, it overwhelms me, and I feel my orgasm approaching quickly.

I want to slow down to recover myself, but Jenny pleads for me to keep going. The urgency in her voice tells me she’s close too. I’m not going to last much longer, not with the sexual intensity between us, built up from our mutual abstinence, and the rush from fucking on the dining room table. Her legs pull against me, and I can feel her high heels tensing just behind me.

“I’m about to cum!” I groan out as a warning.

“Don’t stop, please!” She begs again.

Jenny’s fingers dig into my arms, then I feel her insides clench around my cock, pulsating in her orgasmic release. The excitement and the sensation of her throbbing walls bring me over the edge shortly after. I let out a pleasured huff as I start to cum, my seed being emptied and milked by her hot pussy. We both look at each other, then smile and laugh as we think about what just happened. I slide my arms around her back, then sit in the chair with her on me, and we kiss.


The way Skylar plunges into me with fury is amazing. I started retaking birth control in anticipation of this day, so I urge him not to stop. Most of the time, I’m okay with not reaching my orgasm during sex, but I want it this time, need it. Not only because I want to feel good, but I also need my pleasure to belong to him, to help erase what happened to me. Before my orgasm finishes, I feel his cum spurting powerfully inside me. It’s a silly thought, but I smile as I think of him marking his territory, his thick, sticky seed laying claim to my womanhood.

He pulls me into his lap, and I feel hot, satisfied, and safe. I’ve never felt this before when having sex with anyone else. After we kiss, I tuck my face into his chest, near his collar bone. His body is firm, warm, and he smells good. He puts his arms around me and runs his hands up and down my back. I slide my face up and into his neck, enjoying his scent and the comfort it gives me. I begin kissing his neck, but that isn’t enough, so I lick his skin, then suck on it. I feel his dick firming up inside me again, which is fine because I’m still very horny.

I pull my head back, leaving behind a deep, dark spot on his neck, a mark that he’ll have to live with for at least several days. He’s mine, I think, as I look at it. I placed my heeled feet correctly on the floor then push myself up and down. The friction of our genitals is almost non-existent now, with our cum making a mess of things. It makes for good lubricant, and I slide him wetly in and out of me. He pulls the straps of my dress to the side, and they fall from my shoulders, then his hand tugs it down until he can see my breasts.

As I ride him, my tits bounce openly. He then places his hands on my butt and helps guide my movements. I’m not going as fast or rough as he was, but his hands are telling me to go faster. His cum, mixed with my creamy wetness, is leaking from me and all over his pants. I stop to give my legs a rest, and he reaches up to give my breasts a firm squeeze. I unbutton his shirt and place my hands on his chest, letting my fingers run over his skin. He does the same, and we explore each other.

His fingers tease my nipples until they’re hard again, then toys with them for a while. I watch his face as his attention is on my body, our genitals still connecting us. Behind me, our remaining food is most likely cold now, but that isn’t on either of our minds. Skylar leans forward and kisses the flat part of my chest, just below my neck, then slowly moves down. His mouth latches onto my flesh just above my right nipple, and he sucks hard. When he finally pulls away, he leaves a wet spot, and my skin is a deep color, just like the one I made on his neck.

“You taste good,” Skylar says, smiling.

“So do you,” I say back with a smirk.

“I want to take a picture of you, just like this,” he says, his voice firm, almost like he’s giving a command.

“Okay,” I respond, my insides throbbing some at the thought and sound of his voice. I wonder if he feels it.

Skylar pulls his phone from his jean pocket, then snaps a picture of me. I lean back and pose for him, which seems to motivate him to take more pics. Maybe it’s a bad idea to have such exposing photos of myself in another person’s hand, but it feels good. The more pictures he snaps of me, the more aroused I become, and I don’t know why. I tell him to keep going, then I put my hands on his shoulders and begin to ride him again. I don’t hear the snapping anymore, so I assume he’s recording now. When he aims the camera lower, I lean back more, using the table behind me for support. I try to make sure he can record the way his solid dick vanishes into my body, the way his girth stretches me open. Every intimate moment of ours being saved to his phone. I think about us watching it together in the future. Maybe even years from now, when my body isn’t so tight and fit and when he gains a dad's body.

His free hand finds my clit and rubs it, giving me a sudden increase in pleasure. Each touch of his finger is telling my orgasm to hurry up, and it does. I feel the heat gather in my center at the beckoning of his skilled finger, and I cum. The heat feels like it falls right out of me, dropping down in an orgasmic release. It isn’t until I come down from my climatic high that I realize he made me squirt. We’re both surprised, and it makes my cheeks heat up in embarrassment. His pants and lap are soaked, and so is the chair.

“I didn’t mean to,” I say lowly.

“That was fucking incredible,” he says with an eager voice.

In a flash, his mouth rushes up to mine, and his teeth bite hungrily on my lip. His hand clashes with the flesh of my rear, my dress doing little to protect against the sting. The pain makes me moan, makes me horny. I can’t help but think that my squirting awakened something in him. He pulls back, shoving his phone into my hand, telling me to hold it. I feel him lift me, then we both fall hard to the floor. The arousal overrides any pain from it. He leans into me hard, my legs propped up on his shoulders, and he begins to pound me with absolute ferocity. I try to keep the phone steady, recording each thrust of his hips, which slams his dick deep in me. With a groan, he pulls out, and suddenly I feel thick warmth splattering over my breasts, neck, and face.


The way Jenny squirted, the look on her face filled with pleasure, it turns me on immensely. She appears to be shocked by it, so it’s probably her first time, making it even better. I want to fuck her and need to feel every inch of her slit. Without thinking, I carefully slam us both to the floor and just start banging her as hard as I can. I’m already close and ready to explode, so I pull out and let my cum fly all over her without care. When my cock finally stops, I take my phone back and take a final picture of her. I’m spent, and I can tell she is too.

I lie down on the floor right beside her, both of us downright messy. The chair is wet, and the floor below it has droplets of her squirt too. Several minutes go by before we decide to try and get back up. I get up first, then bring her towel to clean her face with. I wipe the drying cum from her skin, especially around her eyes. There isn’t much I can do to help the parts stuck in her hair. I take her hands, then lift her to her feet. We undress, and she puts our clothes in the wash, then we go to the shower.

I’m surprised that the sight of the water running down her naked body doesn’t make me hard on the spot. Maybe it’s because I’m exhausted, or perhaps it’s because I’m feeling love for her more than anything right now. We take turns washing each other, lathering soap over one another’s skin. This is the first time I’ve ever showered with a girl, and I can’t believe how good it feels to have her washing my body. She leaves my genitals for last, then renews the soap lather before carefully washing me. She looks back and forth from the task to my face, probably making sure I’m okay. I try my best, but there’s nothing I can do to prevent myself from getting hard, not when it’s her touching me.

Jenny continues to clean without a word, bringing the soap over and around my now solid shaft. Even though I’m hard, I don’t feel the urge to have sex, but the way she touches me still feels nice. She rinses me with the water after doing my cock and between my legs and my sack. I then take the soap from her so I can give her just as much attention.


I feel warm and happy, content with being able to wash and touch every inch of Skylar’s body. He takes the soap from me and does the same in return. His hands are firm yet careful with me, cleaning my skin but not hurting me. He follows my pattern, saving my womanhood for last. When he does reach between my legs, I spread them some, allowing his hand to pass easily. I remember how much easier it was to wash between my legs as a guy. Feminine hygiene is a project that never ends. I bleed down there, have to pee from there, and I get wet there. Skylar seems to know this too, and he takes his time washing between my folds, rinsing me often.

To my surprise, he moves on to my hair, taking and applying a generous amount of shampoo to my head. The way his fingers knead and pull through my hair, massaging my scalp, makes me close my eyes. This comes in a close second to the best thing I’ve felt today, right behind my squirting orgasm. It takes a lot of time and patience to wash my hair all the way through, but he does it. He takes the showerhead when finished, then rinses the shampoo from my locks. We turn the water off, and I lay my head against him.

“I love you, Skylar,” I say, hoping that I’m not premature with it.

“I love you too, Jenny,” he responds to my relief and holds me in his arms.

Skylar is stuck wearing one of my girly robes with his clothes in the wash. We go back downstairs and clean up the food and the other mess we made. I make us some tea, and we sit down and talk for a long time. Our relationship took a gigantic step tonight, so we discuss a lot about our future. It’s almost midnight by the time we finish getting a serious feel for each other, our goals, wants, and needs.

“Am I the biggest you’ve had?” Skylar asks, breaking from the adult conversation.

“Why does that matter?” I ask back. Though, I’m sure Nate was about an inch larger.

“Just be honest,” he says.

“Your dick is the only one that’s made me squirt,” I answer.

“Good to know, but that doesn’t answer my question,” he says.

“Fine,” I say. “Nate was a little bigger than you,” I say, trying to get the words out of my mouth as quickly as possible. “You have a thicker head and girth, though, so it feels way better.”

“Okay,” he says. “Why don’t you ask me something personal?”

“Have you ever washed another girl’s hair before?” I ask, hoping that it’s something that can belong only to us.

“You’re the only girl I’ve ever showered with,” he answers, smiling, then I smile too.

We eventually go to bed, and I don’t wake a single time until the sun is on my face. I’m on my side facing away from Skylar, so I roll and place my head on his chest. He wakes a few minutes later and begins to stroke my hair. Each second is a countdown for us having to get up and go to work, leaving each other once more until our schedules line up again. I move closer to him, so my leg can hook his, and I run my fingernail over the skin of his stomach.

I can see him getting hard inside his boxers. With each touch of my fingertip, I move my hand lower, then drag my finger along his stiffening dick. I’m still quite satisfied from our playtime last night and sore too. Even so, I touch him until he’s fully hard.

“It’s just morning wood,” he says.

“Does that mean you don’t want me to do this?” I ask, then move down and wrap my lips around his shaft.

Skylar’s response is only a low moan, followed by his hand resting on my head. I feel butterflies in my stomach and a content warmth around me. I’m not aroused; I don’t crave sex, but I want to make him feel good. I want him to think about me all day when he leaves. Up and down I go, sucking his sexy dick, licking it, and kissing it. His dick is mine, every inch of his hot, solid, veiny shaft with a perfect round tip. I don’t stop until he blows in my mouth, and I swallow it.

“I hope we can see each other again soon, I say,” as I lie down beside him.

“As long as we don’t get a spike of cases at my work, then I’d like to get together in a couple days,” he says.

“I just hope it isn’t weeks,” I say, then I move my eyes to his face as an idea surges in my mind, and I say it without further thought. “You could move in with me,” I say, the words spilling out of my mouth like a full glass. My heart starts to pound.

“You want me to move in with you?” He asks as if seeking clarity.

“I mean, I have a whole house, so I’m just offering,” I say again, trying to tone it down.

“Do you mean move in like, as your boyfriend, or like as a roommate?” He asks.

“As my boyfriend,” I answer, after a brief pause.

“Just so I’m clear,” he says, then sits up on the bed. “You want me to move in and sleep in this bed with you every night. The thought makes me feel warm and tingly, the same thing that would have scared me years ago.

“If you want to,” I say, my voice coming out softer.

“Is that what you want?” He asks, pressing for my true thoughts.

“Yes,” I say, feeling like a vast wall just crumbled into pieces, and Skylar walked over it to seize my heart.

Without a word, he leans into me, his mouth capturing mine. I can feel his energy change as he pulls my body, putting himself on top of me. It’s the same feeling I had when he slammed me into the floor last night. His carnal side erupted again, the part of him that wants nothing more than to have all of me, or at least that what I hope it is.

I imagine that my offer to move in with me has turned him on. He moves down, and I see his dick is hard already. His fingers curl under the waistband of my panties, and he yanks them down roughly. Heat starts to pool in my loins, making me wet just from the anticipation of him being inside me. He moves over me again, his hands on either side of me, holding up the weight of his body. He looks at my face, pausing just for a moment as our eyes lock, then he kisses me—his phone rings, and the dreaded ringtone that’s assigned to his work hits our ears like a water hose on two dogs.

I let my head fall back as I feel the cold air stir back over my body when he moves away from me. By the expression on his face when he answers, I can tell it’s important. I don’t think he even notices when I exit the room to get his clothes. When he finishes the call, I already have his shirt and pants in hand. He tugs me in for a kiss again, then gets dressed. He hurries away, even without eating breakfast, which makes me feel sad. I wonder how long he’ll work without eating today. I lock the front door, and I walk over to flop myself down on the couch. The thoughts of our time together make me smile again, but then I remember he never gave me an answer, not a verbal one anyway.


Skylar and I squeeze in three more dates before he finally moves in with me. He doesn’t do it halfway by splitting time between our places, either. Everything he didn’t need, he sold, gave away, or tossed it. I find space in my house for everything else. I get into the routine of packing food for him to take to work, so I know he can eat. Days pass, then weeks, and months. He makes me happy, and I think I do the same for him. Time also brings us disagreements and arguments. After one particularly bad fight, we discuss ways to prevent them from ruining our relationship.

We take turns, and he goes first. I agree with his idea to never walk away from each other or otherwise give the cold shoulder. My first idea is that we should never call each anything disrespectful, and he agrees too. We continue to exchange ideas, some good, some bad, some ideas coming faster, others taking some time to think about.

“And, we should never tell or ask the other to leave the house or sleep on the couch,” he says, even though that’s never happened. I want him to be with me, even if I’m mad.

“No using sex for leverage over each other either then,” I add.

“What if one of us isn’t in the mood anyway?” He asks.

“Well, we have sex a lot, so I think we have to be with each other at least twice a week, no matter what,” I say. “Except when nature visits me.”

“Why don’t I get a week’s pass too?” He asks with a small smirk on his face.

“Do you want one?” I say, raising my eyebrow, and he digresses. “Thought so,” I say again, trying to sound as snippy as possible.

“Anyway,” he says, pausing to pivot the conversation. “How would you feel about making sex videos?”

“We’ve already made loads of those,” I say.

“I know that. I mean more along the lines of selling some. People, especially couples, can make good money doing that these days.”

“So, you want to put our videos online for people to buy and see?” I ask.

“We can make new ones, just for the purpose of selling. We can probably make more than Leslie,” he says, trying to sell the idea.

“Leslie’s asked me to be in a video before, actually plenty of times, but I always turn her down,” I say.

“Is that a no then?” He asks.

“I mean, is it about the money or the excitement? We’re bringing in good income between both of us,” I say.

“Both, I suppose,” he answers. I think about it for a bit.

“I’m curious now. Which parts of it turn you on? The voyeur? Getting money from our sex acts? Having other guys seeing me?” He hesitates before answering.

“Honestly, and please don’t think I’m weird,” he says. “The thought of other guys seeing you makes me hot. Don’t you have any fetishes?” He asks.

“You already thoroughly fulfill two of them. In fact, you gave me one,” I say, smiling. “You got me into being recorded, and I love being on camera for you.”

“What’s the second?”

“The way you handle me. The way you take everything you want. The way you give me both pain and pleasure,” I answer, looking at his face.

“I’ll keep that in mind,” he says, making a devious expression.


I take a few personal days off from work, but I don’t tell Jenny. She thinks I’m at work and even makes me lunch before I leave, just as she always does. I visit several jewelry stores in my free time, with a specific item on my mind. I want to ask Jenny to marry me, but I want a ring suitable for the way I feel about her. On the third day, I finally commit to one of my potential choices. It’s an expensive ring, but I already cashed in some additional vacation hours to help cover the cost. It’s a black, center stone diamond with white diamonds accenting either side of it along the band. I know she loves the color black and that she doesn’t prefer gold.

I spend a week thinking about how I want to propose. Jenny has never talked about getting married before, so I have no base to start with. At first, I think about having a party, then I remember she isn’t into parties all that much. By the end of two weeks, an idea comes to me when we plan to work out together at the gym. I go over it in my head, what I want to say, when I should ask, and what to do if she says no.

I worry all the way until the day comes, and we arrive at the gym. I keep playing out the plan in my mind. If she keeps to the same routine, she’ll do sit-ups as part of the rotation today. That’s when I’ll make it happen.

Jenny starts things off a little differently, so that makes me worry some. I start to contemplate a different plan in case she doesn’t do sit-ups. That worry goes away when we make our way to the aerobic area. As she gets the mats together, I excuse myself, so I can retrieve the ring from my gym bag. My shorts have pockets on them, but I didn’t trust them enough to keep the ring while we worked out.

My heart is pounding as I walk back to her. I’m so hot it feels like I could pass out. She waits for me, then settles herself on the mat. I look down at her, and even with her hair pinned up, sweat coating her skin, and no makeup, she’s perfect. She asks me if everything is alright, and I nod, then move down to hold her legs. I feel her body tense each time she lifts her torso. Her abs flex as her muscles contract, a view I never get tired of. She finishes the first set, which means it’s time.

I reach in my pocket, taking the box in my fingers as she lies on the mat. I press my thumb against the case, which flicks the top open. I hold it below her leg so she can’t see it just yet. A minute passes, then she’s ready for the next set. She pulls herself up, and I have the ring on display in front of her. She pauses, her eyes confused, then they widen in surprise. She looks at my face, and I feel her legs tense up.

“Jenny,” I say, my voice low and deep. “Will you marry me?”


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