My Unwanted Transition

(Jenny)

My day at work felt like it lasted forever. The only thing I could think about was seeing Skylar. I rushed home as soon as I could and prepared for him to pick me up. Leslie helped me get ready too. I did my eyebrows, eyelashes, cheeks, and lips. He didn't say where we were going, so I was unsure of what to wear. To try and compensate for any outing, I picked out a tight shirt and skinny jeans, along with a pair of heeled boots.

Skylar arrived to pick me up just before I finished getting ready. After a final check by Leslie, I made my way downstairs. It felt like a cliché scene out of a movie or tv show as he stood not far from the bottom of the steps waiting for me. His face lit up with happiness when he saw me, which made me happy too.

"You look beautiful," he said.

"You look good, yourself," I respond with a smile, looking over his button-up shirt.

He moved closer to me, his hands reaching to settle on my waist, his fingers gently rubbing my sides. I stood there silent, nervous, just as each time before. As the moments passed, I expected him to lean in and kiss me, but we just looked at each other.

"Are you sure you want to do this?" Skylar asked. "I mean, giving this, us, a serious chance."

"Yes," I said nodding. I didn't even need to think about it.

"I'm happy to hear that," he said. "Shall we?"

Skylar turned and stepped to the side, gesturing with his hand to have me walk in front. I stepped around him and went outside with him right behind me. He took me to a restaurant, and during dinner, we talked about everything that had happened in the last couple of years. I told him about my job, working out, my new social media craze, and even about getting with my boss. If I was going to be serious with Skylar, I didn't want to keep anything back. In turn, he told me about his job, making detective and the one girl he was with.

"So, are you like some kind of social media celebrity?" He asked.

"No, not really. I mostly just upload post-workout pics," I answered. "I did put up a couple more risqué pics when I reached a hundred thousand followers."

Instead of trying to explain, I pulled my phone out to show him. He took my phone and scrolled through them. I sat there and waited, wondering what he thought since he didn't comment at first. His finger continued to swipe the screen, going through months worth of my pics.

"You have some thirsty guys following you," he said.

"Yeah, I do," I said in a lower voice, realizing that might be a problem. "I can stop if you want," I offered.

"I don't want you to stop if you enjoy it," he said. "I get to have you in person."

"Yes, you do," I said, feeling the heat rush to my face, probably making me blush. "Here."

I got up from the booth and scooted in beside him. I put my left arm around him and held my phone with the other hand. He leaned into me, and I snapped a picture of us, then uploaded it. It was true that I liked sharing on social media, but I wanted to be Skylar's girlfriend too, and I wanted everyone to know.

We walked back to his car after dinner, and when we stopped by the door, he gave me a small kiss. His lips touched and pressed to mine for a brief moment, then pulled back. His eyes looked at mine as the kiss broke, which left me wanting more. Instead, he turned and made his way around the car to the driver's side.

"I have one more thing planned," he said, smiling as he got into the car.

Not long after we pulled away from the restaurant, we arrived at a massage and spa place. I looked around to see if there were any other places he could be taking me, but since we parked right in front, I assumed this was it. The other thing I noticed is that the place looked closed.

"I think they're closed," I said.

"They are closed, but don't worry," he responded.

I got out of the car with him and walked up to the door. Just as we arrived, a lady opened it and stepped out. She gave Skylar a hug, then turned to look at me with a smile on her face.

"You must be Jenny," she said.

"I am," I answered, wondering who she was.

"Aunt Angie, this is Jenny, and Jenny, this is my Aunt Angie," Skylar introduced. "My Aunt Angie owns this place."

"This is indeed my baby," she smiled. "Anyway, come on in."

Angie led us inside, through the empty lobby and into the back. She showed me into a cozy room with a massage table in it, scented candles lit, and a small dressing room in the corner. I assumed that this would be a couple's massage, but Skylar didn't come in, and there wasn't enough room in here for two tables.

"Okay, dear, I'm going to step out, and you can undress to your comfort level. Most people like to remove all their clothes and use towels to cover their bits. When you're ready, go ahead and lay face down, and make yourself comfortable."

I waited for Angie to leave, then I began to undress. The dressing room had hangars to hang my clothes on and a selection of towels. I took one of the smaller ones, which was plenty to cover my bottom. The room was empty as I walked out, so I positioned myself face down on the table just as she explained. There was a cushioned spot at the end to rest my face on.

After a long day of work and a good meal, lying on the table made me sleepy. It didn't take long before I could feel myself almost falling asleep. Before I drifted all the way off, I felt a bit of warm oil being poured on my back, followed by a pair of hands smoothing it over my skin. Their fingers pressing and kneading into the muscles of my back. It was a little weird that there was no introduction, but with me being sleepy and the massage being so relaxing, I didn't care enough to say anything. I closed my eyes, enjoying the feel of their hands, the scent of the oil, and the sound of the rubbing.

Their fingers traveled up and down, from my shoulders and neck to the small of my back where the towel was resting. There was a short pause, then their hands returned and began on my legs. They did each leg from my thigh, calve, and ankle, then did my feet. After another pause, I felt their hands return to my thigh, this time moving up and went under the towel. It made me open my eyes, and my heart sped up from the sudden and unexpected touching of my butt. This was my first time ever getting a massage, so I wasn't sure if this was normal or not.

Either way, their fingers felt good, the way they kneaded and squeezed into my soft flesh there. Their hands moved back down, lowering to the inside of my right thigh. With each press and squeeze, their hands moved higher up my leg until they had to push the towel to continue. As their hand pushed the towel some, I audibly cleared my throat to show a sign of discomfort, hoping they would take the hint.

They pressed into my flesh again, then moved even higher. Another move followed, and their fingers touched where my thigh and crotch meet. They continued to massage, then I felt a light brush against the folds of my vagina, or at least I thought I did. When I felt it again, I moved my hips to shift some. Once I settled, their hand turned and directly cupped my vagina, with a finger sliding up between the folds. I pressed my legs together, but there was no way to guard myself in this position.

"No, I don't need it there," I said, trying to be polite. The only person I wanted to touch me there was Skylar.

"I want to make you feel good," I heard them say.

I lifted my head from the cushion so I could turn enough to see. Just as the voice alluded to me, it was Skylar. I smiled at him and laughed a little, both relieved it wasn't some stranger trying to touch me and that it was him trying to. Without saying anything, I carefully turned over, pulling the towel away from my body at the same time. Skylar's eyes looked away from my face and down my body. He always looked at me like he couldn't get enough.

He put more oil on me, right on my chest, just above my breasts. His hands then rubbing into me just as he did on my back. He moved across my chest, covering my shoulders and collar bone area. I kept looking at his face, and he looked back. His hands moved lower, between my breasts then over them, his fingers gripping my flesh firmly. My nipples were brought to attention by his touch, with the tip of his finger circling them both.

"You've got a lot bigger since the last time I saw you," he said as he squeezed.

"I thought they were never gonna stop growing," I smiled.

"They're perfect," he added before moving his hands down further.

I watched as he touched my flat stomach, his fingers still pressing into my skin. My skin was soft, but the muscles in my abdomen were firm. I could tell he was surprised by the resistance he received when he looked at my face again. It was hard to know if he liked it or not, though. Not all guys were fans of women with fit stomachs like mine. My abs didn't show unless I flexed them, which was the way I wanted it to be.

"You have a tight tummy," he said.

"I've been staying in shape," I responded.

"I can tell. I felt the muscles in your legs too," he said. "Please tell me you have abs."

I smiled, then looked down as I flexed my abdominal muscles. They weren't as defined as most guys would be, but undoubtedly visible as I held them taut. He touched them with his fingers, sliding the tip between each small crevice. Then, despite the oil on my skin, he bent over and kissed my stomach. When I started working out, it wasn't to impress him or any other guy. Now that he was admiring my hard work, I'm glad he liked it.

Skylar kissed my neck, then my lips. I moved my hands up, placing one on his arm and the other behind his head, urging him to kiss me more. I wondered if he was as aroused as me. In fact, if he took me right here on the massage table, I wouldn't stop him. Fortunately, and unfortunately, he stopped. The fire that he ignited inside me wanted to continue, but my mind knew that his aunt was still in the building too.

When we pulled up in front of my house, Skylar smiled at me. I smiled back, happy with the night we shared. His eyes looked at my face the same way he looked at me back then. The same look he had when he put the necklace on me. It made me nervous, but underneath that, I now realized that it feels good too.

"Do you want to come in?" I ask, my question driven by the warmth in my loins.

"I want to," he answers with a half-smile. "But, we are just getting back together, so I think we should take it one step at a time."

"Okay," I say, worried by his answer. I can't help but think he's still wary of me, which he has good reason to be.

He reaches his hand and touches my cheek, giving me one more kiss before we leave each other for the night. It's a soft kiss with just our lips, but a lengthy one. I wonder if he can feel the sexual tension in my body, the urge to have him against me, in me.

(Skylar's Mind)

It takes everything I have to pull away from the kiss with Jenny and not follow her inside. I watch as she leaves my car and enters her house. Even as I drive home, the solid erection in my pants doesn't subside. Jenny's scent, skin, eyes, everything turns me on so much. I think about how she used to be a guy, and the thought should make me feel grossed out, but it doesn't. When I talk to her, look at her eyes, touch her, there's nothing there to resemble a male.

When I get home, I take a shower and continue to think about Jenny. I had fallen for her ever since that night in the mall parking lot. Even when she broke things off with me, I had never gotten over it. I wondered if it was fate that brought us back together at the party. The party wasn't something I wanted to talk about, though, or even think about for that matter. It made me hurt to think about what happened to her.

I shifted my thoughts to our date tonight, from dinner all the way through to giving her a massage. Her skin so smooth and soft, and how much restraint it took to keep me from going too far. I walked to my room, almost finished drying myself, my dick growing hard with every thought. The way she willingly turned over, letting me see her naked brought me to a full hard-on.

I got into my bed, pulling up her social media on my phone as I began to stroke myself. She had given me permission to keep her nudes before, but it didn't feel right, so I deleted them after breaking up. Jenny had plenty of photos online that showed skin, so I scrolled through those. I eventually found a photo of her that was just an ordinary selfie. She was lying in bed with her hair a little messy and wearing a simple t-shirt. My hand moved faster and faster, my fingers gripping. I kept my eyes locked on the screen of my phone as the picture of her looked back at me. All of the intense arousal in me welled up in one spot, then exploded in a cascade of cum, which made of mess of my bare body.

"I had a great time tonight, and I hope I can see you soon," my phone beeped with a text message from Jenny before I could clean up.

(Jenny)

It's late now, so I'm not sure if he'll text me back tonight or not. I know he said he wanted to take it a step at a time, but I can't help but think about him as I touch myself. I lie on my bed fully nude, wishing he was here with me. I reach my phone out with my hand, then snap a picture of my naked body, wanting to send it to him, wanting him to see me, and how turned on I am. It's a terrible idea, though, because it would betray his wishes to take it slow. Even so, I continue to snap more pictures myself, each one a treat I'd like to send but won't.

Before long, I have probably two dozen nude pictures of myself, which I put into a new album called 'for Skylar.' I smile to myself, thinking about the time in the future when he's comfortable again, and I can send these to him. I think back to the ones I sent him a couple years ago before I probably shattered his heart. I wondered if he still has them, looks at them, or even masturbates to them.

Even though I'm still aroused, I decided to finish getting ready for bed without getting myself off. With Skylar so heavily on my mind, I know it will be one of those nights where I can't make myself cum anyway. Though, my decision to go to sleep horny haunts my dreams.

I'm on my knees with a hard dick in my mouth. I look up and see my boss looking down at me from his office chair, his hand on my head. I push down, then pull up with my lips sucked firmly around his shaft. I do it again, then again, moaning softly. I'm the best in my position, not only for work but also in sucking dick. Seven other female managers are trying for the double bonus, each having their own day and chance to give him a blowjob. Only one of us will win, though. I'm the youngest of the managers, and I know I have the tightest body.

The competition is supposed to be only giving head, but I decide to take the initiative. I stand, then turn around, lifting my skirt as I guide his saliva-covered cock inside me. I put my hands on his desk for balance and bounce my body up and down.

I wake up to Leslie standing beside my bed, asking if I'm okay. Apparently, I was moaning and groaning in my sleep. I vaguely remember my dream about so eagerly sucking and fucking my boss. Leslie is quiet, and I realize she's looking at the wet spot between my legs, which stained the bed.

"Girl, you went to bed horny, didn't you?" Leslie asked, but I don't answer. "Here, lemme help," she says, taking my hand.

I follow Leslie back to her room, where she removes my gown. She kisses me as she lets her own gown fall from her body. Her body pressed into mine, her smaller breasts grazing my larger pair. I'm confused, but her lips are soft and taste good. We eventually move into her bed, and I notice the camera on us. The screen on her laptop shows thousands of people watching. I keep looking at the video of us on the computer.

Leslie kisses me as she has me lie back, then moves down, pecking her lips across my skin, my breasts, until she finally reaches her goal, my clit. The camera zooms in on her mouth, focusing on how her tongue flicks my most sensitive spot. The viewers increase each moment, and the chat room seems to get busier as I get closer and closer to cumming.

I open my eyes, and this time I know I'm awake for real. There's a wet pressure I can feel between my legs, and as soon as my fingers graze my clit, I cum. My orgasm is soft, much less intense than the ones I've had in the past, but it still feels good.

(Skylar)

The days at work feel longer now, especially when planning days to see Jenny. Three months went by since she came back into my life, and we've managed to go on six dates. Three others I've had to cancel because of work. Tonight will be our seventh date as long as my job doesn't get in the way again. We won't be going out for dinner, a movie, or to get a massage. Instead, I decided to go to the gym with her. She posts pictures after every visit, making it easy to see how important it is to her. If it's important to her, I'd like to try and be a part of it. Seeing her working out in person, especially anything with her abs, is definitely going to make it challenging to keep from having sex with her.

On the drive home, I think about Jenny. I can tell she wants to have sex, and I appreciate the effort she has put in to respect my request. I still don't know if I'm ready to take that step, though, maybe I am. When I get home, I change my clothes, then drive to the gym, where we planned to meet. I decide that if sex happens naturally today, I will go with it.

Even with my police training, it's hard to keep up with Jenny. The two things I do manage to beat her in are pushups and pullups. Her training routine isn't focused around her arms, though, but rather her mid-section and legs. Tonight is an arm day for her, so I get the pleasure of spotting as she does weights. I notice as she lifts that her breasts seem bigger. They had grown since the first time we dated, but they definitely look even larger now.

Jenny spots for me once she finishes her reps. At the end of the session, she takes a few pictures of herself, then we both go to our respective locker rooms and change. We meet back up after and walk to our cars. It's clear to me after the last few months that Jenny has changed from back then. She seems to have focus and less confusion about her. I hope that it means she's ready to commit fully to this relationship like I am.

"Do you want to come back to my place?" I ask, but she hesitates briefly.

"Um, I mean, I guess I can," she starts, then pauses a moment. "It's that time of the month for me."

"Oh," I say, though not too disappointed. "I'd still like you to come over."

When we get back to my place, I pick out a random movie for us to watch. It doesn't matter to me what it is as long as I get to spend time with Jenny. Truthfully, I was hoping to get more physical with her tonight. It was my choice to abstain from sex for the last few months so that we could build the other parts of our relationship, but my desire to have sex with her is burning deep now.

At the start of the movie, we're sitting upright on the couch, still talking. She shares some things that happened at work, and I do the same. Our conversation fades away as the movie progresses, and we move closer to each other on the couch. We go from sitting upright to lying down on opposite ends. I don't realize how it happened, but I find myself giving a massage to one of her feet. It's hard to tell if she likes it or not since her eyes are focused on the t.v. Either way, I continue to rub, pressing my thumb against the arch of her sole, through her sock.

Without a word, she eventually turns and positions herself on her side in front of me. She then nestles her soft body into mine, facing away. I put my arm over her, which causes us to lock into one another firmly. After a few minutes, I realize how her shapely butt is pressed right against my crotch. I manage to keep myself under control for nearly thirty minutes, then Jenny adjusts, which makes her body rub me. The contact pulls memories of us forward in my mind. I remember our naked bodies against each other, being between her legs, my cock stuffed in her tight pussy. I remember the way her toes curl when she cums, and the way her cheeks flush.