My Unwanted Transition Ch. 07

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Before heading back to the apartment, I got a copy of the house bills, so I'd know roughly how much money I'd need to pay them. At my current salary, I knew that I wouldn't be able to afford it, but if I got the promotion, then I could. Moving back to the house also meant that I'd be leaving Andy without a roommate again. Of course, I did have the option of having him move in with me as my roommate instead.

I waited until the weekend before bringing it up with Andy. It gave me time to think about it myself and if I really wanted to own my own house. When Saturday came, I had made up my mind that I wanted to have the house. Its where I grew up, so there were many fond memories.

As I had done all week, I made breakfast, even though Andy was off from work. We both took our time eating and being lazy in our pajamas. I waited until we both finished eating before bringing up the offer of the house.

"So, my parents told me that they're moving to Florida. And they offered the house to me," I said.

"Whoa man, getting a whole house, nice," Andy reacted.

"Yeah, it is," I said, smiling. "And since I know you needed a roommate here, I wanted to ask if you'd like to move in with me," I offered.

"Um, I actually don't know if I'm ready for that," Andy answered.

"What do you mean? It'll be just like here, except in a house," I asked.

"A house is a big responsibility, especially taking it on with someone else," he explained.

"It's not like we're strangers, though," I said, wondering why he thought it was such a big deal.

"I know, I guess I always thought my first house would be with like a girlfriend or wife or something," he said.

"Oh," I said, then remaining quiet with my thoughts.

"We'll still be close to each other, though," he said, smiling.

"Yeah, I guess you're right," I answered, trying not to sound upset.

( Skylar )

I went back to my room after cleaning up so that I could think about things. Since Leslie was at work, she wasn't responding to my texts. Finally, I decided to text Skylar, whom I had been neglecting. He responded almost immediately as usual. I asked him if he wanted to hang out, and he said that he would pick me up soon. With him coming to get me right away, I didn't dress fancy or anything, just a pair of jeans, a shirt, and flats. I also put on the necklace he had given me. When Skylar arrived, I went out and got in his car.

"I see you're wearing the necklace," Skylar said with a smile on his face.

"Yeah," I answered as I reached to fiddle with it.

"Anywhere you want to go?" He asked.

"Um, it doesn't matter," I answered. "I just wanted to get out of the house.

Skylar started to drive, and we talked some. I told him about my job training and the possible promotion I was up for. He spoke about himself briefly, but kept the conversation mostly about me, asking me questions. Eventually, we pulled up to a park with a long trail and a lake. We walked the complete length of the path, then found a bench to sit by the lake.

"So, you'll find out Monday if you get promoted?" Skylar asked.

"Yeah. I have a final interview, then they'll let us know which of us gets promotions," I answered.

"I'm sure you'll get it," he said assuredly.

"I hope so, then I can finally get my own car," I said.

We talked a while longer, then when we came to a quiet moment, Skylar reached his arm around me on the bench. It was a super cliché move, but I didn't mind. Slowly, he pulled me closer during the conversation. He started to toy with my hair as we got quiet again.

"You're absolutely beautiful," he said.

It felt like my heart skipped a beat from his sudden compliment. As I looked at him, he leaned in and began to kiss me. There was no one around to interrupt, so we made out with each other for quite some time. I started to feel weird about doing this with a guy again, but at the same time, my arousal was growing. My thoughts shifted from it being strange to thinking about how it would feel to have sex with him.

"Why don't we get out of here?" Skylar said as he stopped kissing me.

"Yeah, sure," I answered, almost in a daze.

Skylar drove us back to his place, and we went inside. The moment I stepped through the door, I felt nervous. Each time we had been alone together resulted in us almost having sex. Now, there wasn't anything I could think of that would stop it from happening this time. A horny pulsating was already going between my legs. Before anything could happen, I went straight to the bathroom so I could clean myself up. I checked to make sure there wasn't anything wrong and that I didn't somehow start my period.

To my surprise, Skylar didn't make a move on me right away. Instead, he put a movie on in the living room, and we watched it on his couch. He kept his arm around me most of the time, his hand either lightly running over my arm or playing with my hair.

"You can get more comfortable if you want, like put your legs up," Skylar offered about halfway through the movie.

I took him up on the offer and slipped my shoes off, then turned and put my legs across his. Shortly after, he began to massage my legs, at least doing the best he could since I was wearing jeans. I continued to watch the movie while his hands attended to me, moving back and forth between my calves and thighs. My attention turned to him as he ran his hands down and pulled my sock off, one, then the other. I braced to feel that tickle sensation, but his warm hands and fingers felt good. His thumbs pressed into the sole of my foot, then circling before moving up to my toes.

He rubbed both of my feet thoroughly for much longer than I expected. By the time he finished, I had lost focus on the movie and was entirely laid back on the sofa. Skylar went for my jeans, unbuttoning them, then pulling them down my legs and off. I watched without saying a word as he removed my panties next. He adjusted himself on the couch so he could get between my legs, lowering his head down until he was able to reach me with his mouth. I tensed as his tongue touched my clit, that wet muscle teasing me slowly. He took his time, letting each motion linger before moving to the next. His finger touched my folds, running between them to check how wet I was before pushing into my slit. He drove in and out while keeping his mouth on my sensitive button.

Each time I opened my eyes to look down at him, he was looking up at me. I pumped my hips every so often as the pleasure filled me, but no matter what, he continued to take his time. Sucking, licking, licking, and sucking, his finger gliding in and out of me.

"Skylar!" I moaned, realizing that he was going to make me cum.

My orgasm arrived slowly, then exploded once it reached me. I moaned out and grabbed the sofa on each side with both of my hands. My body was shivering, and my toes were curled in pleasure. I finally opened my eyes when it was over to see Skylar with a satisfied look on his. He stood up and undressed, removing all of his clothes right there. I followed his lead and removed my shirt and bra.

I was ready to suck his dick, wanting to make him feel good too, but once we were both nude, he moved me toward the couch and pushed me to bend over. He placed one hand on my hip, and the other he used to guide the tip of his cock toward my very wet pussy. There was no excuse, no time limit, no period, nothing to stop him from having me. The tip spread my folds, followed by many inches of his manhood filling into me. His hands gripped my hips as he pushed in, then pulled out to push into me again.

"This pussy was well worth the wait," Skylar groaned.

My hands held on to the couch in front of me for balance as he started to fuck me hard. Due to the difference in height, I found myself on my tiptoes often to make the angle better. He pushed me forward until my knees found the couch, his hands moving from my hips to my breasts, squeezing them as he continued to drive his cock into me. From there, he turned me some to face longways on the couch, then pushed me down onto my hands.

He leaned over me more, my breasts still in his hands, his mouth now biting my shoulder. It was a pleasurable pain, one that made my insides throb. His hand moved from my breast to my hair, his fingers wrapping it just enough to tug on, making my head pull back.

"Does this dick feel good in you?" Skylar asked, holding my hair firmly.

"Yes," I answered softly.

"Does it feel good?" He asked again, pulling my hair even more.

"Yes!" I moaned loudly.

Skylar pressed his body against me, pushing me lower until I was almost flat against the sofa, my hips being the only part raised since he was still inside me. His hand pressed against my back, keeping me pinned down as he fucked me roughly. His second hand moved between my legs so that he could rub my clit. I moaned into the sofa, my toes curling again as I started to cum. His hand moved from my back, then I felt a powerful slap land on my rear, which echoed in the room. I barely finished my orgasm before he pulled out of me and exploded his cum all over my butt and back.

I was so warm and tingly that I didn't want to move or get up. Skylar lifted my legs and sat down, then started to massage me again. Finally, I decided to get up and did so carefully, since I had his cum all over me.

"Do you have a towel I can borrow, so I can take a shower?" I asked.

"I do," he said, smiling, then went to retrieve one. "Here you go." He handed me the towel and leaned in to kiss me.

In the shower, my mind kept replaying it all. The way he touched me, the way he handled me, the way he fucked me. It was like he gave me a whole lot of things I never knew I wanted. I stayed in the shower until the water started to turn cold, mostly because I didn't know what I could say now. He had ravished me. It felt incredible, but I also felt like a large chunk of my remaining masculinity had been stripped away.

As I opened the door, I found my clothes stacked in front of it that I had left in the living room. Instead of having to walk out in just a towel, I dressed in the bathroom, then went back to Skylar.

"You should stay the night. I'll order us some food, and we can actually finish the movie," Skylar offered.

"Yeah, I'll stay," I said after thinking about it shortly.

We ate and watched the movie, then watched random things on t.v. That continued until I eventually fell asleep due to the gentle touching Skylar was giving me with his hands. When I woke up, it took me a moment to remember the day before and that I agreed to stay over. I remembered falling asleep on the couch, but as I sat up, I realized I was in a bed. When I turned to look, I saw Skylar beside me, already awake.

"Good morning, beautiful," he said as he moved close enough to kiss me.

"Mm, good morning," I responded.

"Does this mean we're official now?" He asked.

"I suppose it does," I answered.

"That definitely makes my day," he said with a grin.

I turned to put my feet, finding that I didn't have my jeans on. If he was able to take my jeans off, I must have been sleeping good. I saw them across from me and went to get my phone out of the pocket. Since I hadn't looked at it while I was with Skylar, I needed to see if I missed anything important. There was a missed call from Leslie and a couple of texts from Andy.

"I thought about the house thing all day, and what I said. I know this might sound stupid, but what if we were like boyfriend and girlfriend?" If it's dumb, just tell me," Andy texted last night.

I felt a surge of emotion that took everything I had to contain it, which was interrupted by Skylar putting his arms around me from behind.

"Why don't we get some breakfast?" He said.

"Actually, I think I should head back home," I responded.

"Why? Is everything alright?" He asked.

"Yeah, I just have that big promotion interview coming up, so it's distracting me," I said, using that as an excuse.

"Okay, if you want to go, I'll give you a ride back."

12
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6 Comments
CharletteCharlettealmost 2 years ago

GIGGLES,

Again, we all knew it was going to happen !

But I am enjoying the working up to each of the major happenings.

This author is pretty good at surprize turns in the story.

The conflicting feeling Jen is having about which guy she wants is starting to drag on and on.

I feel this subject needs to come to an end. There have been plenty of other setups to expand on.

That is my opinion anyway !

AnonymousAnonymousover 3 years ago
dam so hot

I really wish I was jenny but she now has to decide which guy she really wants to be with my choice would be andy if he really wants to be boyfriend and girlfr

TerraficTerraficover 4 years agoAuthor

I like your insight and the way you seem to understand Jen!

AnonymousAnonymousover 4 years ago
Confusion

There’s no option at this point in that the transition can be denied so better to go with the new then hang onto the old, meaning not sure how this character would feel it’s best to stay with a guy who knew she’s a guy and just using for selfish reasons. This character owes it to herself to know be fully treated as a girl and what comes with being an actual girl

TerraficTerraficover 4 years agoAuthor

I'm not sure if I'll expand on the cam girl thing yet. I do have some ideas involving your second idea though, which will most likely be included in the future.

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