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My Unwanted Transition 15


Leslie, Alice, and I are out looking at wedding dresses again. Its already been nearly six months since Alice and Andy were married, and the date Skylar and I set is quickly approaching. Each time I fit myself into a dress, my heart speeds up at the sight of me wearing it. I picture myself from years ago, still being a guy, imagining what it would be like to have a wife. Instead, I’m preparing to be a wife myself, about to be married to a man I love deeply.

It takes me weeks to settle on a dress, which I get my mom’s approval on before I finalize. My mom is ecstatic over the wedding, seemingly even more excited than I am. My dad is in full support of me too, which makes me feel relieved and happy because I know how fathers can be with their kids. Leslie makes sure the house is clear before we bring the dress in, and we store it in her room for now. Part of her room looks like a professional movie studio with lighting, cameras, and backdrop. My mind fills with thoughts of being in front of them, streaming and recording me for whoever wants to see.

“That’ll keep it safe until your big day,” Leslie says with a smile.

“Thanks,” I say, but my attention is still distracted by the cameras.

I hear my cell ringing, which brings me back to reality, and I go to answer it. My district manager is calling everyone together for a meeting this evening, so I let Skylar know I won’t be able to cook dinner. I shower and dress in a blouse, skirt, stockings, and heels, then drive to the meeting. All department specialists are here, seven of us in total, and Mike, the district manager, which makes eight. Five of us are women, which always makes me conscious of the fact that Mike has probably had sex with all of us. None of them have brought it up before, and I don’t plan to either.

“I know this is a late meeting, but unfortunate circumstances call for it,” Mike starts. “I will be resigning from my position and moving out of state, effective immediately. Before you ask, I have a very sick relative I will be caring for, and I don’t wish to go into detail.” He looks at the group. “Any questions?”

“First, I want to wish you well, but yes, one question,” one of the guys says. “Any idea who will be replacing your position?”

“Yes, that is one reason I called the meeting,” Mike answers. “The VP has picked my replacement,” he says, then looks toward Shane, the other guy. Shane is tall, probably a few years younger than Mike, but in good shape.

We all take turns giving him congratulations, though I’m sure I’m not the only one who feels cheated. Out of two men and five women, it feels like a slap in the face that one of the men get promoted. We begin to exit once all information has been given. As I’m about to step through the door, Mike calls me back.

“Jen, I don’t usually share my personal feelings about the company’s decision, but since I’m leaving, it doesn’t matter,” he says, leaning on his desk. “I wanted you to get the promotion, but the VP picked Shane.” I don’t know how to feel about it.

“Thank you for considering me,” I say. “And, I’m sorry to hear about your family.”

“You’ve also been kind and respectful to me,” he says with a small laugh. “No matter how perverted or disrespectful I might have been, you always remain professional.”

“Except for when you first offered a promotion in exchange for sex, I’ve never had an issue with you,” I say.

“What about when I took advantage of you while you were drunk?” He asks.

“I wasn’t that drunk,” I say. “I knew what I was doing, and I chose to have sex with you.”

“Fond memories,” he smiles. “I hope you have a happy marriage, Jen.”

He hugs me, and I hug him back, tighter than I usually would. His arms embrace my body fully, keeping me in place, his hand sliding down until it’s right on my butt. His other hand moves down as well, releasing his grip on me, but I don’t move. He squeezes my ass with both hands, which takes me back to our one-night-stand. I remember how he bent me over my own couch and fucked me like a slut he picked up from the street. If was I wasn’t engaged, I would likely allow it to happen again, but Skylar has helped me gain some self-control. I reach back and gently stop him until his hands pull away from me.


I see Jenny pull up in the driveway from where I’ve been sitting all evening, dreading the conversation I have to have with her. When she walks up to the door, I open it for her, then greet her with a kiss. Her smile makes me smile, too, giving me a moment of comfort before I have to give the news. I ask her to sit with me, and her changed expression tells me she knows something is wrong.

“I don’t know how to say this, so I’m just gonna be blunt,” I say. “I’ve been assigned to a special, deep cover assignment, and I’m probably going to be away for over a month.” I pause and wait for her reaction.

“A month?” She says, frowning. “I guess you can’t tell me what the assignment is either.”

“I can’t, but it’s serious business,” I say.

“I understand,” she says. “Please be safe; I want you to come home to me,” she adds, then notices my clothes. “You’re leaving tonight, aren’t you?”

“Yes,” I say.

She moves from her chair into my lap, placing her legs around me, her soft body sitting on mine. Her hands push under my shirt with cold fingers, then slide up my chest. I look at her face, seeing the slightly sad expression she has. Her eyes dark with makeup, accenting her beauty, though she doesn’t need it. Her hair smells like fruit, and I pull the tie from it so it falls down to its full length. I put my arms around her, drawing her into me firmly, holding her body against mine. I feel her relax, her shoulders become less tense, and she rests her head on my shoulder.

After a few minutes, she moves again, and I feel her lips touch my neck. The tip of her tongue is warm, soft, and wet, and it makes my cock jump. Her hands move down my chest, then pull my shirt up until I assist her in taking it off. I move my hands down her back and over her butt; she flinches some.

“Are you okay?” I ask, worried I caused her pain.

“I’m fine,” she answers. “My manager, Mike, announced he’s leaving today, and before we left, he decided to get a last feel in.”

“A last feel?” I ask.

“We hugged, then he grabbed my ass,” she says.

“Oh,” I say, pausing. I should feel angry, but I don’t. “Is that all?”

“That’s it. I pushed his hands away, then we parted ways,” she says. “I’ll never cheat on you, Skylar, ever.”

“What if we made it okay,” I say, knowing how sudden it would sound, and maybe it’s just my arousal talking.

“Made it okay to sleep with my boss?” She asks, furrowing her brows.

“I mean, what if we had an open relationship? Ever since we did it with Alice and Andy, its been on my mind. I’ve even watched your video with him several times.” She perks up on my lap.

“How would that work?” She asks, seeming more interested than upset by the idea.

“I think we could be with additional partners in a responsible manner. We just always make sure to share with each other what we do.”

“You like the thought of me with other guys,” she says, then smirks. “Do you jerk off while watching Andy and me?”

“No, but almost. I save my energy for you,” I answer. “Is that a yes, then?” I ask.

“You’re in charge of our bedroom,” she says, then leans to put her mouth by my ear. “And, my tight, wet pussy,” she whispers, then looks at my face.

Her voice and comment make my dick jump. With my time running out before I have to leave, I reach and pull her blouse open, then unhook her bra. Before long, she manages to pull my cock out, then stands up on her high heels before squatting back down and plunging my stiff phallus into her depths.


I wake up from a nap, then begin to prepare for my next cam show. Once my computer, mic, and camera are all ready, I head downstairs to get my water and protein shake. I hear Jenny and Skylar in the kitchen, but I don’t expect them to be naked and fucking when I walk in. I turn to walk away, but Skylar tells me to go ahead.

The chair is creaking as I go to get my drinks, making a sound every time Jenny goes up and down. Sex doesn’t make me uncomfortable, but I try to avoid looking out of respect. As I make my shake, I hear a mix of their moans, and in between that, Skylar goes on about how good Jenny’s pussy is, and she goes on about how good his dick is. They’re corny lines, but the real, intimate passion between them gets me turned on.

I take my shake and water, then walk past them again to leave, and this time, Jenny asks me to stay. Not only to stay but to watch, too. I’ve seen Jenny naked before, so that isn’t new. However, I do like the sight of Skylar in such a vulnerable position. He’s nearly naked with his shirt off and his pants around his ankles. Jenny stops and stands, then Skylar helps her remove her skirt and panties. I get a nice look at Skylar’s stiff dick, glistening in the light from Jenny’s essence all over it. She sits on him again, and that sexy rod vanishes into her body, then partially appears over and over as she rides him.

No porn I’ve ever seen is as hot as watching it live like this. They move from the chair to the table once Jenny’s legs get tired, and Skylar fucks her like a street slut. He thumbs her clit expertly, and her responses tell me he knows how to make her feel good. Despite not being attracted to other women, I’m sorely turned on by watching Jenny orgasm. She barely has a chance to finish before Skylar pulls out and blows a massive load on her body.

“Fuck! That was hot. Feel free to invite me to watch any time,” I say.

I don’t find out until the next day that Skylar will be gone for a while, so I do what I always do, and take Jenny for a manicure and pedicure. By the end of the second week, I can tell how much she misses him. She doesn’t have the same energy or drive when coming home from work, nor does she take the time to cook. I want to spend more time with her, but the guy I’ve been seeing and shooting videos with has been taking me out more often. His name is Samuel, or Sam for short. He’s a tall, black American that I met at the gym when he helped me with weights.

I’ve never invited him over, nor any guy for that matter since the incident with Nate and Jenny. I want to introduce him to Jenny soon now that I’ve committed to a relationship with him. A few days later, when Sam drops me off, Jenny comes home as we make out in the doorway like in a movie.

“Hey Jen,” I say. “This is Sam, and Sam, this is Jenny.”

“It’s nice to meet you, Jenny,” he says politely.

Jenny is happy to see me with someone, so she cooks dinner with me, and we invite Sam in. I take the time to catch her up on how we met, giving her all the details, except for the more juicy ones I’ll give her later. Jen leaves us after dinner, so I finally take Sam on tour in my room. Until now, we’ve made our videos at his place, and now that Jenny knows him, he’ll be able to come here.


My assignment leads me to the sister of a suspected human trafficker by the name of Claire. She’s in her thirties, no apparent job, but she likes to run on the track several times a week. Her hair reminds me of Jenny, who I miss deeply right now. I know the sooner I can retrieve actionable information, the quicker I can get back to her. I work up my approach, then initiate contact as a professional masseuse. It takes some work, along with some lingo I picked up from my aunt to get her to bite. After a long conversation, cautious questioning, and getting a feel for me, she schedules an appointment for Saturday.

I use my time between now and then to borrow gear from my aunt again. On Saturday, I arrive at her place promptly. She lives in the city, twenty stories up in a highrise condo. I lug the table and other necessary items with me, then find her door already open and her waiting.

She leads me to a mostly empty guest room that’s only furnished with a bed, dresser, and t.v. I set the table up and then ask her to get comfortable while I step out, wanting to use the precious minutes to conduct a quick search. She insists that I stay with her, so I do. I avert my eyes to the floor, wall, or anywhere that isn’t her getting undressed.

She finally settles on the table while wearing a two-piece bikini. I try to hold a careful conversation hoping that she might drop a clue to help my case. It isn’t until I reach her ankles that a topic of interest comes up, which is how she manages to live here without a job. She begins telling me about her brother and that he pays for the place in return for handling some finances. It occurs to me that she wouldn’t share this information if she knew what kind of business he was involved in. This information also means there may be some evidence present here.

Claire turns over, then I make my way back up her legs, body, and shoulders. That should be the end of the session, but she announces that I’m not finished just yet, then leads my hand to her breast. I steel myself, then massage both of them until she sits up and removes her top. I explain that this is outside my profession's duties, to which she tells me to do it or get out without pay. I can’t leave yet, nor can I blow my contact with her without finding evidence.

She lets out a soft sigh as I knead her flesh, and I focus my mind on Jenny. A bottomless, troubling pit of betrayal forms in my stomach. Claire urges me to continue, pushing my hand with hers until we reach her crotch. She warns me again that I need to finish or leave as my fingers are led inside her bikini bottom. Her fingers keep pushing mine until I’m rubbing a circle on her clit, eliciting a moan from her. I feel my dick spring up despite my feelings. She tells me how long it’s been for her due to her brother’s protectiveness; five long years without sex.

Another soft, pleasured moan fills the room and also fills my guilt. I pull back and stop, unable to go through with it any longer. Claire looks at me, anger slowly overtaking the pleasure in her eyes.

“I apologize, but I really need to use the restroom,” I say, trying to buy time.

“Well, hurry, it’s right in there,” she says, pointing to an adjacent door.

I step into the bathroom and take a deep breath before quickly looking around. There’s nothing of interest in here, except minimal toiletries for guests. Knowing my time is limited, I quickly text Jenny with a small summary of what happened.

“A strange criminal woman wants to have sex with you?” Jenny texts back.

“I don’t believe she’s a criminal, but her brother is, and she might have evidence here,” I say.

“Don’t take too long; I’ll be back in one minute,” I hear Claire call out. I call Jenny.

“If you tell me no, I won’t do it,” I say as soon as she answers.

“Did your job tell you to do this?” She asks.

“No,” I answer. “We aren’t supposed to have sex with suspects or leads, but I believe it’s the fastest way to get enough evidence for a warrant, then to rescue the victims.”

“What victims?” She asks, and I explain. “And this evidence will save a lot of people?”

“It could, yes,” I answer.

“Then you have to do it,” she says.

“I can’t if it means I lose you,” I say.

“Just come home to me safely, Skylar,” she says. “I love you.”

Claire comes back in just a few seconds after I go out of the bathroom. “I hope your tongue is as good as your hands,” she says. I find myself lying on the bed with her mounting my face. Her thick, warm thighs encompass my head as her womanhood inches up to my face. Even with Jenny’s approval, I still feel guilty, but I push ahead and begin to lick and suck, anything to make her feel good. Claire leans forward and opens my pants, then pulls my waiting, erect cock out. Again, she tells me how long its been, then sucks it into her mouth.

I find myself matching her speed, going faster or slower as she does with me. After only a couple minutes, she swings herself off me. She turns, then pulls a condom out from wherever she was keeping it. Her fingers tear the package to retrieve the rubber, then she rolls it down my shaft. Her phone rings, causing her to let out a very irritated screeching sound. She huffs that she has to take her brother’s call, then storms off.

I check to see if it’s clear, then hurry to look around. I go from room to room and cabinet to cabinet while naked with an erection and condom on my dick. In a random drawer, I find bank records containing account numbers, names, and more. I snap them one by one into my phone, then quickly shuffle back to the guest room.

“I hate to give you blue balls, but I have to leave,” Claire says as she comes back. “Why don’t you come back at the same time next week?”

“I’ll put it on my calendar,” I say.

I head back to the safe house used for cover and keeping files related to the case. Everything I managed to get on my phone I send over to the department for review, hoping it’s enough for a warrant. The next day, we get the warrant, which eventually leads to Claire being in protective custody, arrests, and the recovery of some trafficking victims. Claire’s brother, however, isn’t caught.

I share every detail of my encounter with Claire with Jenny as soon as I get home. She has me tell her the story several times, especially the part where I have to sneak around naked.


The days leading up to our wedding are busy. My parents are in town, I’m getting my hair done, my nails, toes, everything. I barely get any sleep the night before, yet I’m full of energy. My mom and Leslie help me dress, making sure everything is perfect. My heart is beating so wildly, I feel like it might leave my chest and go for a run down the street.

When the last preparations are made, my dad comes in and asks my mom and Leslie for a moment. He always has a poker face, making it difficult to tell what he’s thinking. His eyes move over me and my dress as he completes a circle.

“You know, I enjoyed having a son,” he says. “You were quite the kid, even though you never got into sports or other things dads cheer their sons on for. But, you were a good kid, always getting good grades and not getting into much trouble,” he says, emphasizing the word, ‘much.’ “I honestly didn’t know how to feel when you- changed. Now that I stand here and see how happy you are, it makes me happy. And before I give you away to Skylar today, I want to say how proud of you I am. No matter what, you’ll always be my daughter.”

Heat rushes to my face, making tears form in my eyes as he hugs me. He pulls a handkerchief from his pocket and catches my tears.

“We don’t want to mess up your makeup,” he says. I smile.

“Thank you, daddy,” I say.

The music begins to play, my dad secures my arm and leads me down the aisle. Our friends and family turn to look, all of their eyes gazing upon me like I’m a celebrity. It takes everything I have to fight back more tears, so I try to focus on Skylar. His face lights up when he sees me like I’m a gift under the tree on Christmas, and he’s just a kid.

I stand in front of him as the ceremony continues, but I barely hear anything being said. I’m stuck in an isolated world with him, and all the guests are outside of it.

“Skylar Mclean, do you take Jenny Clayton to be your wedded wife, to live together in marriage? Do you promise to love her, comfort her, honor and keep her for better or worse, for richer or poorer, in sickness and health, and forsaking all others, be faithful only to her, for as long as you both shall live?”

“I do,” Skylar says.

“Jenny Clayton, do you take Skylar Mclean to be your wedded husband to live together in marriage? Do you promise to love him, comfort him, honor and keep him for better or worse, for richer or poorer, in sickness and health, and forsaking all others, be faithful only to him, for as long as you both shall live?”

“I do,” I say as my lips pull into a smile wider than I could ever muster in the past or future.

Skylar takes my hand, wedding ring in the other, then looks at my face, into my eyes, into my soul.

“Jenny, may this ring serve as a symbol of my love, commitment, and bond to you, forever,” he says, then pushes the ring down my finger. I take his hand.

“Skylar, may this ring serve as my symbol of love, commitment, and my bond to you, forever,” I say.

“I now pronounce you husband and wife; you may kiss the bride.”

Skylar embraces me, leans me back as far as he can, his strong arms holding me with ease. His mouth seals upon mine, and we kiss. It’s such an intimate kiss that it provokes a variety of gasps and cheers from our guests.

“Jenny! That was amazing!” Leslie almost screams as she runs up to me afterward.

“It’s Mrs. Mclean now,” I say with a big smirk.

Being a bride turns out to be hard work, everyone wanting your attention, pictures, thoughts, and more. At our reception, I end up dancing with person after person, from Skylar to Andy and my dad to some of Skylar’s family. Skylar finds me taking a break from the crowd by a set of chairs tucked in a hallway. I smile at him, happy to have a moment with just us, and I rest my head on his chest, breathing in his scent, which relaxes me. His arms hold me against him, gently rocking both of us. This isn’t how I ever pictured my life being, but now that I’m here, I know it’s exactly what I want. Skylar encourages me with his words, then takes my hand and leads me back to the guests.

(To the future – Jenny)

I stare at the wedding ring on my finger, a symbol of my partnership and lifetime commitment to Skylar. He’s my husband, and I’m his wife. His wife, I say in my head a few times. The term makes me smile. I used to think about having my own wife, hoping that she’d be everything I’d want and that I could make her happy. Who knew that I would be a wife to another guy.

When I came home from the medical center after having everything about my manhood stripped away, I hated this body. I remember the new weight of my growing breasts being a constant reminder of my loss. The slit between my legs was another reminder, one that kept me aware of my missing penis.

Every day, week, and month brought more changes to me. I saw things differently, heard them differently, smelled, tasted, and felt them all differently. My body changed more and more, devouring my masculinity and slowly replacing it with the body of a woman. My thin frame filled out, shaping my figure into a series of curves with a small waist and wider hips. My fingernails grew longer, as did my hair.

I remember Andy being there for me, even if he did take advantage of the situation somewhat. He’s a guy, and suddenly his best friend was a very accessible female. Leslie definitely made my life easier, being a pillar of support and helping me learn to live a new life.

I smile when I think about Skylar. We met him at the mall, and even back then, there was some exhibitionism already waiting somewhere inside me. I was attracted to him right away, which I suppose is why I watched him masturbate in the parking lot.

The last important figure in my new life has to be my former manager, Mike. Even though he tried to blackmail me, the incident made me strong. I stood up to him and got my promotion. Despite all his faults, I learned a lot from him, and he treated me well outside the aggressive flirting. I’m still unsure why I decided to have sex with him, but I must admit I liked it quite a bit.

I look forward to my life with Skylar, the happiness we’ll bring each other, and the challenges we’ll overcome together. There’s still much more of my sexuality to explore as well, which he’ll help me unlock.

I’m Jenny Mclean, formerly Jenny Clayton, formerly Jason Clayton. This is my life, and I wouldn’t trade it for anything.

(Author’s note)

In February of 2017, I posted the first chapter of this series with the intent of doing a quick and fun story. I want to thank all of my readers for encouraging me to continue writing and building this into the largest story I’ve ever written. I hope everyone has enjoyed reading as much as I did writing it. With that being said, I will continue to add stories for Jenny’s world in the future under a new title, called “Jenny’s World.”

These stories will take on events in the past, present, and even adding more to her future. You’ll see more point-of-views from other characters, just as I’ve started doing in the last few chapters as well. Please let me know if there’s anything you’d like to see!

Thank you!



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