My First Time Getting Fucked

I had fucked girls and even fucked my best friend in the ass but now it was my turn to get fucked.

As a kid and into my teen years I had a kind of boyfriend. His name was Jayson and we would masturbate together and then it progressed to giving each other blow jobs and ultimately it lead to anal sex. All of that took 7 years to progress to. Jayson and I would continue this secret sexual relationship well into our 20’s and I always was the top and he always the bottom.

There was a kid in my neighborhood that I also fooled around with when we were in high school. He was 2 years younger than me and we would just watch porn together and Jack off. His name was Jo. The furthest thing we did was, kissing, I would Jack him off and I’d grind on him with no penetration until I came. It was entirely because he didn’t want too because he was too scared I guess.

Jo had a sister that was my age and I was more or less in love with her but despite being in most of my classes and living 2 houses down from me for 12 years, she didn’t know I existed. Jo and I would have sleep overs once in a while and he’d steal some of his sisters bra and panties. I’d sneak into my mom’s drawers and swipe a pair of bra and panties or a couple pieces of lingerie she had. We’d wear them all the time when we’d masturbate or he’d dress up in his sister’s stuff and I’d pretend he was her or vice versa.

Nothing ever really came of it and I moved away after high school. I was gone for 3 years and decided to move back home. I was 21 now and starting to understand myself sexually more and more each day. I knew I was bisexual at this point, no more denying it. While I was away I had some interaction with a couple guys. Never anything more than exchanging blowjobs.

About a week after I moved back home I saw Jo in the neighborhood and we had a little conversation. It started as a “hey, what’s up?” and “whatcha been up to?” kind of talk.

That night I laid in bed, horny as fuck thinking about Jo. Being bisexual is kind of weird sometimes. Some days you wanna fuck a girl silly and some days you just want some guys dick in your mouth.

I had been away for 3 years and Jayson was always an option, but something was different about this night. I had been thinking more and more about being fucked in my ass. I had always fucked Jayson’s ass and he never mine. Jayson’s dick was as big as mine and kind of scared me.

I was so horny and turned on in recent days about being fucked in my ass. I decided to go to the sex shop and I bought 3 different dildos. A small, medium and large sized one. The small one was only about 5”, the medium 7” and the large was a thick 10”.

I got home and used the small 5” one. It was uncomfortable for sure at first but I got used to it and it felt amazing. I advanced to the 7” and it felt amazing as well but I had reached my limit. That was about Jayson’s size and I wasn’t sure if I could handle it.

Jo had a smaller dick and I immediately turned my attention towards him. I called him and we made some small talk and I casually steered the conversation towards “the old days”. That’s what we called the times when we’d fool around.

I was surprised to find out that he was openly bisexual as well. I had always thought he was straight and just fooling around with me because it felt good. He admitted that he had never had anal sex but he was getting better at oral.

I had enough talk, I wanted him and I wanted him now!

Jo came over and I opened the door, grabbed him by his shirt and pulled him inside. Closing the door with one hand and leaning in I kissed him. He was taken back a bit but then realized how turned on I was when I kissed him a second time this time with my tongue. We had never done that before. I lead him to my bedroom and my mom passed us in the hallway and said hi to Jo. When we got into my bedroom I closed the door and blocked it with a milk crate I had full of junk. It was at least 50 pounds of crap blocking the door.

I pulled Jo’s pants down and started sucking his cock. Jo’s cock wasn’t very big, less than 6” and it wasn’t very thick either.

“I’m gonna cum!” Jo mumbled

I didn’t want him to cum in my mouth, I wanted it in my ass but before I could spit his dick out and tell him to stop because I had bigger plans, I felt a spurt of hot cum hit the back of my throat and I just finished him off.

“Oh my god that was insane!” Jo said seemingly very relaxed

“Well, I have had some practice in the last few years.” I answered

“Want me to suck you?” He asked

“Yeah if you’re willing.” I responded

“Definitely.” Jo said with a smile

He sucked my cock for about 10 minutes. He wasn’t very good at it, there was some teeth involved, not much hand work and even less tongue. It wasn’t going to make me cum and he had already said that I couldn’t cum in his mouth so I lied and said I was gonna cum and then just jacked off into his hands.

It was kind of a good thing that he came as fast as he did because as soon as his cock hit my lips, I started getting nervous as fuck and I would’ve chickened out for sure.

Jo spent the night, and we slept naked in my bed together which was a nice surprise. We masturbated together once more before falling asleep and then again in the morning. During the night we talked a bunch and I told him about how I still loved wearing womens clothes. I had a small collection of bras and underwear, a pair of jeans and a mini skirt. I had a couple tops and a full dress. I also had some lingerie.

The next day Jo and I had nothing to do so we hung out together and I had decided that tonight was the night, no matter what!

Jo told me he wanted to see my womens clothes so I modeled them for him for a bit.

“You look hot in those clothes!” He said obviously turned on.

At that moment I had decided that the best way to avoid chickening out again would be to tell him. Less likely to chicken out if he’s expecting it and knows about it I thought.

“You like seeing me in women’s clothes?” I asked

“Oh yeah!” He answered back eagerly sitting forward and running his hand down my thigh.

I felt something I had never felt before. I felt what it was like to be a woman when a man looks at her with that lustful eyes. I could see he wanted me now as much as I wanted him.

I couldn’t leave him hanging so I pulled his cock out and sucked him off once again. He came just as fast this time as well.

Once we settled down he mentioned how hot it was to see me sucking his cock dressed as a girl.

“Tonight I’m gonna let you fuck me!” I blurted out

Jo’s jaw dropped and was speechless. I was embarrassed for sure but now it was out there. I thought, of course there’s a way out but I pretended there wasnt.

“Do you want me to dress up for it?” I asked

He was obviously excited and agreed to seeing me dressed up. The more I thought about it the more excited I got. I went as far as suggesting we went shopping and get some more stuff and a new outfit. He was unbelievably excited about that idea.

We had to do this carefully so not to let people at the stores know what we were doing. We had talked about what to get and he mentioned that he was really into a more business look.

We went to the mall and walked awkwardly into a womens clothing store. I told the older lady that we were brothers and looking for an outfit for our moms birthday. It was stupid, I doubt she believed it but nevertheless helped us. Of course she asked what size our “mom” was and I told her she had a similar frame as I did.

In the end I got a white silk blouse, a black jacket and skirt to go with it. The rest we’d have to get at the sex shop.

We walked into the sex shop much more relaxed and not worried about people staring or criticizing. I got a black garter belt and black stockings, a pair of black lace panties and a matching bra. I thought it was enough but then we saw this chest piece deal that was fake silicone tits. They looked kind of stupid but I figured why the hell not.

We got back to my place and I was slowly going over everything I had and just how expensive this was. Kind of beginning to regret it until I started putting the stuff on. I looked amazing and felt amazing!

We had to wait a few days before we could do anything with it, I didn’t want to dress up like a woman and get fucked with my mom in the next room.

My mom went out with some friends on a Saturday night and we had our chance. I called Jo that morning and told him to come over for our date at 8pm. As the day went on I got more and more nervous and more and more excited. My mom noticed my behavior was a little off and asked why I was being weird. I just mentioned I had a date that night.

Mom left around 7 and it gave me an hour to get ready. I feared it wasn’t enough time as I had a few more ideas that I wanted to try.

I rushed to the shower and cleaned myself as fast as I could. Dried myself, checked the clock, 7:14. I put on the black lace panties and the garter belt. Pulled the black stockings up to my thigh and clipped them to the belt. The bra I had bought was too small for the fake boobs piece that I bought so I had to run to my moms room and find a bra that matched my panties. I had one in mind but when I got there it was gone. Mom must’ve been wearing it. I just grabbed the next best thing, a plain white bra and put it on. Struggled with fitting the fake chest piece in but eventually got it. Checked the clock. 7:41!

Quickly pulled the skirt up and zipped it. I went into the bathroom and reached into my moms makeup drawer. Quickly put on some red lipstick and black eyeliner. That was extent of my makeup abilities at the time. 7:50! Please don’t be early!

Threw the white blouse over my shoulders and buttoned it up and tucked it in my skirt. Threw the jacket on over it and buttoned it as well. I had picked up a black wig the day before as a surprise and threw a pair of my moms high heels on. 8:02! Gave myself a quick look in the mirror and got unbelievably turned on! I was so hot! I’m not the most attractive guy, not ugly by any means but damn I made a hot woman.

I heard a knock on the door and my heart skipped a beat! It was pounding so hard I thought I was gonna pass out. I quickly reached in my skirt and pushed my cock and balls between my legs and answered the door.

“Who is it?” I asked just in case it wasn’t Jo.

“It’s me.” Jo replied

I opened the door but stayed behind it so he couldn’t see me just yet. As I closed the door he turned towards me and again, his jaw dropped.

“Oh my god!” He yelled. “You look gorgeous!”

“Thank you.” I said back in my softest voice.

I locked the door and took his hand and lead him to the living room. I was surprised at how well he looked. He cleaned up nicely. He had shaved and combed his hair. He smelled nice and was wearing a nice button up collared shirt. I knew then that this was important to him as well as me. I calmed down a bit then.

I sat next to him on the couch and placed my hand on his leg.

“You look nice too.” I said softly. “You smell like a man and it’s sexy.” I added as I put my hand on his cheek and kissed him as soft as I could on the lips.

I wanted to go all out for this now that I saw him and saw how serious he was as well so I got up and made us a small dinner. It was nothing special but it added to the mood.

When we were done we went back to the couch and started kissing. As my tongue broke the barrier of his lips and began swirling with his, my nerves began to get to me again. It was getting more real and progressing now.

His hand began to rub my thigh and slide up my skirt a bit. I stood up and took his hand and lead him to my bedroom. I closed the door behind me and he sat down on the edge of the bed. I went to my moms room and grabbed a few of her candles and brought them in and lit them. I shut the light off and sat next to him. The candlelight was the perfect amount of light and set the mood exquisitely.

We returned to making out and groping each other. It was getting too much so I got down on my knees between his legs. I began to unbutton his pants but he pulled me up to my feet, grabbed my arms and kissed me again. He unbuttoned my jacket and blouse and I removed them and threw ‘em on the dresser top. My fake tits were revealed to him now and his kissed my cleavage and worked his lips up to my neck and nibbled my ear.

His hands reached around and squeezed my ass a bit and then he unzipped my skirt. I shimmied a bit and it fell to my ankles. I kicked it aside and then did the same thing with my panties. I returned to unbuttoning his pants and pulled them down. As he kicked them off, I ran my hands under his shirt and lifted it off him. The tips of our dicks swung a bit and hit each other causing a chill thru my body.

“Lay down.” Jo said as he steeped aside and took my hand. “Do you want me to eat your pussy?” He asked

I loved that he was so into this that he said pussy. Even though the last time he sucked my cock it was less than impressive, I was so happy he called it a pussy that I let him.

I laid on my back, and he grabbed the base of my shaft and put the tip in his mouth. I immediately felt his tongue swirl around the tip and his hand started stroking the shaft.

“Oh wow, that feels amazing!” I moaned out absolutely NOT faking it.

“I’ve been watching videos on how to do this better.” Jo said as he spit my cock out for a second.

“Oh god it shows!” I moaned

It still wasn’t a world class blow job but it was definitely an improvement from the one a week earlier. I was so lost in the moment though that it felt incredible.

“I’m gonna cum!” I moaned out and this time I meant it. He was gonna make me cum!

He didn’t stop sucking and I thought maybe he didn’t hear me so I tapped the back of his head. He didn’t even take my dick out of his mouth, he just mumbled.

“Just cum in my mouth this time.” He mumbled

I couldn’t believe he said that. I lost control of everything at that second and shot a hot, huge load of cum in Jo’s mouth. He gagged on it a bit and spit it onto my balls and legs a bit but immediately put my cock back in his mouth until I was done cumming. It wasn’t picture perfect but again, it was so far beyond my expectations. Jo stood up and spit the rest in the garbage.

“I can’t believe you did that.” I said surprised. “How was it?”

“Not as good as I hoped, better than I thought.” He answered. “I could get used to it I think.”

“Awesome! You did a really good job.” I told him

I was off topic with my surprise but quickly regained focus. I sat up and started kissing him again.

“You ready to fuck my wet pussy?” I asked in my most seductive voice

“I haven’t stopped thinking about this all week. I’m so ready!” He replied eagerly

I reached into my side table drawer and grabbed a tube of lube. I laid down on my back and took his hand and pulled him on top of me. We started kissing again.

Over the past few years I had wondered more and more what it was like to be a woman and have a man inside me. Now there was a man on top of me and it was about to happen.

“Do you want me to wear a condom?” He asked

“No. I think we’ll be ok.” I answered

I pushed him up off me and grabbed the lube. I squirted a big glob into my hand and began stroking it all over his cock. I rubbed what was left on my asshole and slid a finger of it inside as well.

“Just do what I say and nothing more ok?” I said

I laid back down on my back and lifted my legs up exposing my asshole to his cock. He scooted closer to me and I felt his cock hit my hole.

“Put the tip against it and push gently.” I told him.

He did as I asked. He put the tip against my hole and pushed. He was hesitant to push I could tell.

“Push a little harder.” I said to him but nothing happened. “Harder, get just the tip in. I can handle it.” I explained

He did push harder and his tip slipped inside me. I gasped and put my hand against his stomach signaling for him to stop pushing. It was at that moment that I felt he had some decent abs. Not chiseled but I could feel some definition for sure. Suddenly that took over my mind and I relaxed a bit. I had been practicing quite a bit with my dildos and once I calmed down, it was smaller than the 7”. He felt just like my 5” dildo.

“Go for it! Fuck me!” I said as I wrapped my legs around his waist.

I thought he’d be gentle at first and work his way up to harder as he came closer and closer to cumming but he just went for it. His hands wrapped around my thighs holding me in place and he started pounding my ass.

I felt so incredibly happy. I was fulfilling a sexual fantasy that I had for a while. I knew what it felt like to be a woman, kind of. I was dressed sexy, and I had a man inside me for the first time.

I felt beads of sweat dripping from Jo’s nose onto my stomach. He was doing a great job!

“Oh my god I’m gonna cum!” He shouted

“Cum inside me! Get me pregnant!” I yelled back trying to stay in the moment but instantly thinking that was weird.

He had one final hard thrust as deep as he could go and I could feel cum spurting into my hole. I pulled him down by the neck and started kissing him as passionately as I could. I was so unbelievably turned on!

As he pulled his cock out, I felt cum trickle out of my ass. I couldn’t believe how perfect this night went. Everything went exactly as I wanted it to. I got my cock sucked adequately and I got fucked for the first time.

“That was so hot when you told me to get you pregnant.” Jo confessed

“Really?! It felt weird.” I responded

“Anything to keep us in the moment and not thinking about anything else is good.” He said

“I need a shower. I’m covered in sweat and cum.” I said laughing

I jumped in the shower and began cleaning myself again. A minute later, Jo joined me. We kissed a bit, washed each other’s backs and despite each of us having erections we didn’t do anything sexual.

We dried off and put on some comfortable clothes. He had a pair of shorts and I told him not to wear a shirt. I wanted to smell him and feel his abs some more. I put my fake chest piece back on and wore my blue silk nightgown. We cuddled on the couch and watched a movie until I heard my mom pull into the driveway. We raced to my room and shut off the lights and got into bed.

“Is there any way we can continue doing this?” Jo whispered

“You mean the role playing or just having sex?” I asked

“I love the role play! I want that!” Jo said excitedly

“Are you asking me to be your girlfriend Jo?” I said with a giggle

“Yes.” He answered

“Good, because I’m pregnant with your baby.” I said laughing.

This got much longer than I thought it would. Thanks for finishing it, there’s more, WAY more. Jo and I got weird for a long time.

To be continued….

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