My Unwanted Transition - Cover

My Unwanted Transition

Copyright© 2020 by Terrafic

Chapter 14

Erotica Sex Story: Chapter 14 - A guy has to change from male to female due to a freak condition. This is a first-person account of their struggles, failures and triumphs as they adjust.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Reluctant   Heterosexual   TransGender   Fiction   Science Fiction   Cream Pie   Masturbation   Oral Sex   Safe Sex   Slow  

(Jenny)

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.

(Skylar)

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.

(Leslie)

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.

(Skylar)

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.

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