My Unwanted Transition Ch. 03

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"I guess we can take our clothes off," I finally said.

We stood and started to undress, both pausing in our underwear. I could tell Andy was already hard from his cock pointing against his boxers. I had on matching bra and panties, which I had gotten used to until my best friend was looking at me. It suddenly felt weird to be wearing girl's underwear, except Andy didn't seem to be thinking that way. His eyes were gazing at me like I was some cute girl.

"Can I touch you?" Andy asked.

"Well, we have to touch to have sex," I answered.

"I'm gonna touch you then," Andy stated, then stepping forward.

I wasn't sure what to do, so I just stood there. Andy reached his arms around me, then I felt his hands come to rest on my butt, his fingers squeezing some. It felt incredibly weird, and I avoided eye contact, keeping my head lowered and my eyes toward his body. His hands didn't linger too long and moved up, grazing my back until he found my bra and started to unhook it. Once it was undone, my bra loosened and he pulled it away, exposing my breasts to him.

"Nice tits," Andy complimented.

"Are we gonna do this?" I asked, changing the subject to avoid blushing.

"Okay okay. How do you want to do? On your back, doggy, on top?" Andy asked.

" So romantic," I joked.

"You said just sex, nothing else." He rebutted.

"Yeah, but you don't have to be so formal," I clarified.

"So picky, just like a girl, jeez," he laughed.

"We don't have to do it at all," I chimed back, feeling my emotions getting hot.

"Yup, just like a girl, getting all cute when you're mad," Andy teased.

I blushed, feeling a slight flutter inside and some anger building at the same time in a rush of emotion. Andy's hands came back to my hips before I could walk away and pushed my panties down. When they hit the floor, he took his own underwear off and quickly embraced me, leading me to the bed. I fell on back with him between my legs and felt the tip of his cock touching my pussy. It wasn't until he talked that I realized how fast I was breathing.

"Are you okay?" He asked.

I tried to calm myself, feeling a throbbing tingle between my legs. Arousal was flooding my body, and I felt so hot, it was like we had a blanket over us. I didn't want to sound shaky, so instead I talking, I nodded to him. There was some pain, which took me a moment to realize it was Andy's cock pushing into me. I could feel it inside of me, making me stretch. The pay dimmed away slowly, but there was still a pressure feeling, like a rubber band around your wrist.

"You're so wet," Andy groaned lowly.

I still didn't say anything. He was starting to move now. I felt his cock sliding out, then before it went all the way, it pushed back in. The sensation made me tense up, and before I could try and comprehend it, Andy pulled back and thrust again, giving me the same feeling. Over and over, I felt his cock take my pussy. My head was turned, and I was looking at anything but him. It was so embarrassing.

"Does it feel good?" Andy asked.

The new sensations had overwhelmed my mind, and somehow I hadn't processed if it did feel good or not until he asked. I focused on each thrust, the way it felt and the sensation it gave me. It felt good, very good, so much so, that the very next thrust caused me to let out a quiet moan. That must have given Andy some encouragement because he grabbed one of my breasts and started to touch my body. His hips began to move faster, causing a reaction in my own body that made me lift my hips toward him.

I felt him embrace me more and increase his effort. Without realizing it, my legs were up and partly around his waist. I could feel a faint hint of my orgasm in the distance, but every thrust didn't bring me closer which was frustrating. I tightened my legs a little more around him, trying to angle my body so that his cock would enter me just the right way. As I moved my hips around some, I felt that stronger sensation more often, which pushed me closer each time. I looked down at his cock moving in and out, still unable to believe that I really had a cock inside of me, inside of my pussy.

"I'm gonna cum!" I moaned out.

The feeling of my climax was building steadily now. I reached down and rubbed my clit to help my body along. Andy started to get faster and rough, which set me back rather than help me finish. I reached my hands to his waist, trying to signal him to slow a little, which he did. He looked down at me, driving his hips firmly into my body. I was very close now, and I could feel my body starting to shiver. My arms reached around his body, my legs clasping tightly around him as well. My orgasm flushed through my body, making me tense. In that rush of pleasure and emotion, I leaned up and kissed him. It was a wet kiss, his tongue entering my mouth as his body came to rest on me. When the kiss finally broke, everything felt hot, and I realized he had stopped.

"What are you doing?" I asked.

"Just enjoying the moment," Andy answered

"Yeah but, why did you stop? You're making it weird." I said, our faces still only inches apart.

"Your throbbing pussy made me cum," he said, giving my lips another kiss, but I didn't kiss him back.

"You came inside me?" I asked, feeling my heart starting to pound against my chest. "Let me up."

"Whats wrong, didn't it feel good?" Andy asked, moving to the side.

"It did, but I don't want to get pregnant." I got up and went to clean myself up.

"How are you going to get pregnant?"

"Um, I'm a girl remember?" I said sarcastically.

"I know, but you don't have all of that, right?"

"Yes, I do. I have it all, everything. I get periods too, remember?" I was starting to get a little upset.

"Fuck. I'm sorry. It just felt really good, I completely forgot."

I was pacing back and forth some, getting more nervous and upset by the minute. My mind was just picturing my future with a baby and having to dedicate all of my time to that. It all boiled up inside of me and quickly.

"I don't want to have a baby!" I said in frustration, feeling tears welling up in my eyes.

"You're not gonna get pregnant," Andy said, sounding confident.

"How do you know?" I asked, responding sharply.

"They have morning-after pills, you know? In the morning, we can go and get some." Andy stood and walked over to me. "Does that sound good?"

"Are you sure that'll work?" I asked, feeling some relief.

"It should." He confirmed.

"Okay," I said, wiping my eyes.

( The morning after. )

When I woke up in the morning, the bed was empty, and Andy was already up and about. I couldn't believe I slept so good with what happened. The bed felt comfortable, so I didn't get up right away, even though I wanted to go and get the pills, and maybe even some condoms. Eventually, I sat up and stretched, then put a hand on my stomach to make sure it wasn't getting bigger, even though I knew it was silly.

"Good morning sleepy head," Andy said.

"Good morning," I replied.

Before I could get up, Andy tossed a box at me. I clearly saw it gliding through the air, and tried to catch it, but it hit me right in the chest. I was surprised to see that it was the pill. The pack only contained a single tablet which was weird, but I guess it made sense since it was for emergencies and not for actual birth control.

"The pharmacist said you should take something for nausea too since it's common. I have some Pepto and stuff in the bathroom."

"You talked to the pharmacist?" I asked, thinking how sweet the effort was.

"Oh yeah, I wanted to make sure I got something good because I don't want a baby." Andy laughed.

I shook my head, feeling that moment go down the drain. It was for the better anyway, I thought to myself. I didn't need to have those kinds of crazy thoughts and feelings. In the bathroom, I found some nausea medicine and took it along with the pill, then joined Andy for breakfast, which was cereal.

"I really liked it last night," Andy said.

"I did too, except for when you tried to get me pregnant," I said sarcastically.

"Next time I'll just cum on your face," he snickered.

"Or you can just wear a condom. No glove, no love as they say." I smirked. But seriously, we need to talk about this if we're gonna keep doing it," I said, looking at him, expecting a joke.

"You're right. How do you think we should handle it?" Andy responded very maturely.

"I don't know really. I guess I could talk to my doctor about getting birth control. I don't know anything about this stuff, and I don't want to ask my parents because that would be weird." I sighed.

Our conversation carried on for quite a while, discussing a lot about avoiding babies, how often we should have sex and even where he was allowed to cum. Even after talking for over an hour, we didn't really agree to anything in stone. Andy didn't mind having a list of some sort, but I thought it made the whole thing too formal.

"Anyway, what do you want to do today?" I asked, moving on from the subject.

"All this sex talk makes me want to have sex again!" And answered.

"I think I rather wait until I get birth control or something. I'm still nervous about this whole thing." I looked at him.

It went quiet for a minute, and I knew Andy was trying to think of some way for us to have sex again. I could see it in his face that he was thinking, so I just shook my head at him.

"Don't worry, we will do it again," I said, trying to assure him so that he would drop it.

From there, Andy did leave it alone, and we went on to play some more games. It was different hanging out with him now that we had sex though. I kept thinking about how it felt to have a guy touching me the way he did, the way he felt inside of me and even how we kissed. My mind held on to how wrong it is that I had sex with a guy and that I'm not gay. Everything that happened felt good though. I enjoyed every moment of what happened except for the little incident. This was going to take time for me to adjust to, with my mind having been trained as a guy my whole life. I didn't know if I ever would get used to it, but at least I did feel comfortable about being a girl these days.

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CharletteCharlettealmost 2 years ago

WELL ?

We all knew it was going to happen eventually !

I so hope Jenny does not have to pay the price of her first time sex, for the rest of her life !

Also I hope we get to read more about her friend from work. That nail experience can lead to so many wonderful new joys, excitement and happy things that seem to be restricted to the female members of humanity .

This author seems to miss some good opportunities to transition from one paragraph to another by simply leaving gaps of unexplained time which disrupts the flow of the story.

AnonymousAnonymousover 2 years ago

Brilliant! I read it for 2nd times.

I love whole Jenny story an I am little bit envious for her... Hot & desire. Really very good job #Terrafic.

AnonymousAnonymousover 3 years ago
dam so hot

I really want to jenny or find away to go through that surgery too

LisaBrooksLisaBrooksover 5 years ago
Benefits Being A Female!

This has moved on to another moment in Jenny's life! I envy her for being a female every day! I wish when I was 20 ish I had what Jason had to become Jenny! I sit here wondering about myself and how a Jenny could become me! It all intrigues me!

AnonymousAnonymousabout 6 years ago
Please keep it..."cumming"

Amazing story keep it up

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