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I Never Saw This Coming Sex Story

#Gay #Group #Mature #Trans

By Chucky Sue

A wild night of kinky fun lead me to a life changing decision.

I’ve been a cross dressing bisexual freak since I was 13. I absolutely love being with women. The feeling of my cock sliding in and out of their warm wet pussies is unrivaled. However, I get more satisfaction from being with a man. It goes back to my obsession with my mom. Since I was old enough to get a hard on I wanted to fuck my mother. It was my soul purpose as a teen. So much so, that my cross dressing comes from my mother. I couldn’t have her so I started dressing up in her clothes and eventually began having sex with men all while fantasizing about me being her while I was being fucked.

I’m in my mid 40’s now, still a momma’s boy and still a bisexual cross dressing freak. I am definitely a BBW when I dress up. I weigh 310 pounds and have B cup boy boobs. I have long natural red hair, pale skin (I’m a ginger) and aside from a little patch of red pubic hair, I’m completely hairless.

About 6 months ago I was at a gay/trans friendly bar dressed up in women’s clothes and I noticed a tall black man that I recognized from work. His name is Marcus and he just started working at my workplace. I didn’t want anyone from work to know my secret but before I could make my escape, he had noticed me and made his way over.

At first he didn’t recognize me so I decided to play it cool like I wasn’t interested in him but as we chatted for a few minutes and I saw him up close for the first time I realized how fucking hot he was!

Marcus is 6’2”, 46, divorced, and has the sexiest mustache! He’s also in good shape, and well dressed.

We talked for over an hour and he didn’t say anything about recognizing me and I just kind of lost myself in the moment and eventually I agreed to go back to his apartment.

We had sex twice that night, and I ended up spending the night with him. I thanked him for a fun night with a morning blowjob and then I went home.

The following Monday I was terrified to go to work. Certainly he would see me. And of course as soon as I walked in the front door, there was Marcus talking to the receptionist about, of all things.. me!

I stood behind him for a minute or so eavesdropping on his conversation before he finally noticed my presence and turned around. Had he been talking about anything else I would’ve avoided him but I knew as soon as I heard his voice what and who he was talking about.

As he turned towards me he instantly recognized me and I asked if he wanted to go talk somewhere. He agreed and we worked everything out quite easily. We also agreed to meet up that night after work for drinks. We then agreed to go back to his apartment again. We then had sex 3 times! We then continued to hook up every night after work the rest of that week. By the end of that week, we had sex at least 20 times, and we ultimately decided to be in a relationship together.

Suddenly, unexpectedly, and not even considered a possibility, I was his girlfriend. Whenever I was with him, I was dressed as a woman, except for when I was at work. It wasn’t long before I had clothes and toiletries at his apartment since I was spending almost every night with him.

It’s been six months and we’re still going strong. Truthfully I have never been so sexually satisfied. I no longer fantasize about being my mom. I only think about Marcus’ 8” cock inside me!

A couple nights ago we were having drinks at the same bar we met at. We had a few drinks already when two guys approached our table. A thin but athletic white guy and a taller equally athletic black guy. Immediately it was obvious Marcus knew them as they began talking like bros. They were talking sports for a few minutes before Marcus finally introduced me as his “girlfriend” (which made my boi pussy wet). Apparently the two guys went to the same gym and play basketball together on weekends.

The night and conversation progressed as the two guys had joined us now. Despite feeling a bit out of place it was still fun. We continued to drink and talk. There was even a bit of flirting and sex talk, well more like boys talking like boys.

“Your friends are kind of hot.” I whispered in Marcus’ ear feeling unbelievably embarrassed as soon as I said it.

Apparently Marcus’ alcohol was working as well as mine was because he smiled at me, rubbed my thigh under the table and leaned over and whispered in my ear.

“I agree.”

Before I could even think and or respond, Marcus leaned across the table towards his friends…

“My girl thinks you guys are hot.” Marcus said with a smirk.

“Oh yeah?” The two guys reacted with smiles and laughter

“Whaddya say babe, are the hot enough to come home with us?” Marcus asked me

I knew exactly what they had in mind. Honestly I didn’t hesitate. I was drunk for sure but not to drunk I couldn’t make decisions. I said “absolutely YES!”

We all made our way to what Marcus and I now call “our apartment”. There was no small talk or drinks. We went straight to the bedroom.

I was the last to enter the bedroom. They were all lined up waiting for me. Marcus in the middle, and the other two guys on either side of him. I approached them and put my hands on Marcus’ hips and we began to make out. Within seconds the other two closed in and surrounded me. I had six hands groping me and three mouths kissing my lips and neck. I also felt three hard cocks pressed against me!

Marcus and his two friends began to ravage me. First they removed my clothes aggressively. Marcus and I were still kissing passionately. The white guy was kissing my neck and stroking my throbbing erection. The black guy had his cock pressed against my hip, groping my tits and squeezing and slapping my ass. I had never had so much attention! Suddenly I felt the black guy toying my ass with his finger and then it slid inside my hole. I gasped as I had begun sucking on Marcus’ neck. I instantly lost it. I came like a storm!

Despite cumming I was still unbelievably turned on. All I could think about was pleasuring these three men! I got on my knees and all three of them pulled their cocks out. I opened my mouth and Marcus slid his cock inside. I reached up and took the other two dicks in my hands and began stroking as Marcus fucked my mouth. I began to gag a bit and tears started rolling down my face.

The white guy was the first to position himself behind me. He splashed some lubricant on my hole and then his cock and pushed himself inside me effortlessly. I don’t know if I was so turned on and relaxed that my hole was already loosened up or what but I’ve never had a cock slide inside me with such ease the first time.

As the white guy began to pound my ass very aggressively, squeezing my hips as hard as he could, I was still sucking Marcus’ cock. The black guy stood next to Marcus and dangled his cock in my face. He had a beautiful cock! Holy shit! It was at least 9 or 10 inches. Skin was super tight and his veins were huge! I began to switch back and forth between their cocks. I was being spit roasted by three guys!!!

“Lemme see if that ass is as good as her mouth.” The black guy said

I was never more excited to get a cock inside my ass!

The black guy got behind me and pushed his beautiful dick inside me. I gasped! It felt incredible! For the next hour, Marcus’ two friends switched off and fucked me as played with and sucked Marcus’ dick. Marcus seemed far more interested in watching them fuck me. He was encouraging them and intently watching them. His friends each came inside me twice in that hour, Marcus didn’t cum once.

When the black guy was done fucking me for a second time, then Marcus got behind me and began to fuck me. He was only inside me for 10-20 seconds before he let out a load moan and came inside me! The other two congratulated him as he pulled his cum soaked cock from my exhausted ass.

We all sat there and calmed for a few minutes before I got up and headed to the bathroom to clean up. As I entered the bathroom I noticed all three men were following me.

“Get in the bathtub and get on your knees.” Marcus said squeezing my chin and kissing me. I did exactly as he told me. As I got on my knees and looked up towards them, they were all lined up. A warm stream of piss hit my face from the black guys dick. Then one from Marcus and finally a third from the white guy. Three streams of hot piss now hitting my face. I opened my mouth. They all pissed in my mouth.

When they were done, Marcus instructed me to get up. As I stood up drenched in their piss, the black guy grabbed me by the hair and lead me back to the bedroom.

“Get on your knees” the black guy said

I got on my knees and I couldn’t believe they all were hard as a rock again! I began sucking and stroking all three of them. I was exhausted but I wasn’t going to stop! I was having too much fun!

Each man took turns fucking me until the came inside me again. First the black guy. He sat on the edge of the bed and I rode him reverse cowgirl for what felt like forever. In reality it was more like 10 minutes before he finally pushed me off and sprayed his cum in my face. Immediately after the white guy got behind and fucked me from behind. He went quickly. After just a minute or two, he stood up and added his spunk to my cum and piss covered face.

Marcus wanted me to ride him. I straddled him and began to grind on his cock! He reached up and fondled and pinched my nipples. I love having my tits played with! It made my cock hard!

As I continued to ride Marcus, my cock got harder and harder. It slapped against his stomach.

“I’m gonna cum!” I shouted

As I began to explode all over Marcus’ stomach, he began to fuck me as hard as he could. Before I could finish cumming, he had thrust himself as deep inside me as possible and exploded! He let out this primal grunt!

My ass hurts like a motherfucker!

I realized I’m in love with Marcus and I think he is in love with me. I think I’m going to start living as a woman all the time for him. We’ll see how that goes….

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By Chucky Sue
#Gay #Group #Mature #Trans

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