Roommate’s Girlfriend Has A Surprise pt.2 Sex Story

#Bisexual #Group #Trans

By Dubya

The morning after Mark’s first time with a beautiful trans woman gets even more interesting…

So after a night of hot fucking with Trina, the trans girlfriend of my roommate Tim, we awake to find him and my girlfriend Shellie standing over us, totally nude themselves.

“So, Mark, did you enjoy fucking my girl? I’ll bet she fucked you good too! Didn’t she?”

Tim moved around to my side of the bed and spread my asscheeks to inspect my abused rectum. He was taking liberties that would’ve gotten him knocked out the day before. I guess he was entitled now since I had fucked, and been fucked by, his girlfriend Trina. I really wasn’t surprised to find him in my room and we lived together. Why my girlfriend Shellie was there was the real mystery. And why was she nude? And why didn’t either of them seem mad?

“Yep! From the looks of your poor hole, you got reamed pretty good, buddy! Are you sore?”

“Ummm… I haven’t really… checked.”

I felt around, and yes, my asshole was pretty tender.

“Yeah, I guess I am. She has a pretty big cock.”

The day before that, I would have never thought those words would come out of my mouth. “She has a pretty big cock.” I mean, really! I never had gay or bi tendencies, but I had a marathon fuck session with a trans girl with a big cock and loved it! I guess that would make me pansexual.

“Were you surprised by what Trina was packing, buddy? Did you have any idea that she was trans?”

“No, I didn’t have any idea. Yeah, I was pretty surprised. I… I never had intentions of… sleeping with her either way. It… it just happened.”

I looked at Shellie, who had sat on the bed next to Trina, and said, with all sincerity, “I’m sorry, Shel, really. I…”

Shellie cut me off with, “Forget it, babe. We both have our little side adventures. My girl’s night out last night was really a girl’s night in. We had had a lesbo threesome, complete with strapons. I just didn’t think this would happen. You really didn’t realize Trina is trans?”

“No. Really. I had no idea. She’s so pretty… I noticed that there was something different about her, but I never knew what.”

Trina was lying there quietly, not saying anything. Then Tim said with a chuckle, “Don’t lie there acting all innocent, Trina. I know you wanted it to happen. You even cleared it with me first.”

Trina finally spoke, “Yeah, I did. Something about Mark just turns me on. If I really had a pussy, it would be wet around him. Since I have a cock, he made it hard… and wet.”

Then she turned to Shellie and said, “I’m sorry, sweetie. I just couldn’t help myself. And by the way, you are even hotter naked than I thought you would be! Damn, girl! I like girls too, ya know!”

“Sure, sure,” Shellie giggled, “you’re just trying to distract me from the fact that you fucked my boyfriend by flirting with me, you slut.”

“That’s me! Trans slut! I’ll fuck anything that moves! Just like my slutty boyfriend!”

Tim laughed and said, “Yep. I like it all. Pussy, cock, ass. Doesn’t matter girl, boy, trans. I got a blow job from a female stripper last night. You had no idea about that, did you, Mark? Honestly, I’ve thought about fucking you myself!”

I answered, “I knew you were horny, but not how horny! I guess I might consider that now that I’ve tried cock. Thanks for sharing Trina with me! Uhh… have you two… shared… each other?”

Shellie popped in. “This morning. Tim found you two all cocooned together like this this morning. I came over earlier than intended, and he brought me in here to show me. So we figured, what the hell, and went at it ourselves. You two must have really worn each other out! We made enough noise to wake the dead, and you still didn’t wake up.”

“Well, I guess all barriers have been broken down between the four of us. What now,” I asked.

“Well, buddy, I asked if you two were ready for more fun,” said Tim with a grin. “So how about a foursome?”

I looked at Trina. She smiled and nodded, saying, “Yeah, I want to fuck Shellie.”

“That’s good, honey, because I want some of that big cock myself. You’ll be MY first trans too. I want to play with those cute titties while I’m riding that monster!”

“We’ll make that happen, sugar, just let me clean up first. I felt asleep right after fucking Mark’s sexy virgin hole. I didn’t get the chance to wash up. Neither did he, and he ass fucked me too.”

“Well, get your sexy ass in there and get to it!” Shellie playfully swatted Trina’s pert ass as she passed her.

Trina looked over her shoulder at me and said, “I’ll bring you a wash rag, Mark.”

“Okay, sweetie,” I answered. Sweetie? Did I really just say that to her? I looked back and forth at Tim and Shellie. Neither of them seemed to notice, so I didn’t say anything more about it.

Tim asked me, “So, how surprised were you when Trina’s big cock sprung out? Did you think about running away?”

I replied, “Strangely, no. I just grabbed hold of it as we kissed. I had never thought about touching a cock before that, but I just… needed to feel it I guess is the only way I can describe it. Like I was possessed.”

Tim smiled and said, “I get it. I was a teenager when my cousin and I started playing with each other’s cocks. The first time, I felt compelled to touch it and suck it. I always liked girls, but after that, I knew I’d like cock the rest of my life too. I’ve been with other trans girls before Trina, but she’s the first one I’ve had a relationship with.”

Shellie popped in with, “Yeah, I felt the same way about my first pussy. It was a friend that was sleeping over. We were 10 at the time. We were talking about sex and masturbation. We took our panties off and started diddling ourselves. Next thing we knew, we were diddling each other. Then French kissing while we finger banged each other. That led to licking each other. Like Tim, I knew I loved boys and cock, but I’d love pussy and titties after that too.”

“I guess I led a sheltered life. I never had any cousins or friends approach me for anything like that.”

Trina came back in with a warm wash rag and washed off my cock. We all sat there for a minute quietly before Trina asked, “So, how are we going to do this?”

Shellie spoke up first. “I know what I want! I want all three of these beautiful cocks in me at the same time! Trina, I said I wanted to play with those cute titties while I ride your girl dick, so you get my pussy. Tim, I’ll blow you. And Mark, baby, you know how I love when you shove that hefty cock up my ass. So, sound good, kiddies?”

The three of us looked at each and nodded enthusiastically.

“Yep,” I spoke for the three of us.

Trina got on the bed on her back. She and Shellie made out, getting Trina’s girl cock nice and hard. She had two fingers in Shellie’s pussy, ensuring that it was nice and wet. I had no desire to kiss Tim, but I did play with his cock, and he played with mine. After a few moments, I bent over and took him in my mouth. My second cock. It wasn’t as big as my first one, and Tim didn’t shave his like Trina, but I enjoyed sucking it.

After a few minutes Shellie announced, “Okay, boys, let’s do this!”

She straddled Trina and impaled herself on her huge girl cock. Trina immediately started sucking on Shellie’s huge tits as Shellie ground herself on that beautiful girl cock. Tim got into position and Shellie started blowing him. I grabbed the lube and greased up my cock and Shellie’s puckered asshole. I lined up, then shoved my dick home in the ass that I had come to know so well.

I always did love fucking Shellie’s ass, but she was really the one enjoying herself. Her mouth was full of Tim’s big cock but her moans were still filling the room. The squishing sounds of Trina’s 9 inch cock filling Shellie’s wet cunt were almost as loud as her moans.

The four of us got a good rhythm going. We were like one big literal fucking machine. I could feel Trina’s cock through the membrane separating Shellie’s cunt and asshole. That felt amazing! I’d fucked Shellie up the ass dozens of times over our two year relationship, but it felt so much better with that cock in her pussy at the same time.

Tim was the first to cum, shooting his load all over Shellie’s big tits. She held them up and together for him as he wanked his orgasm to its finish. She then fed those cum covered monsters to Trina, who greedily licked them clean.

To my surprise, Tim got behind me and started licking my asshole. I groaned at the pleasurable feeling of it. After it was nice and wet, he shoved his middle finger, then index finger in it. The stimulation on my prostate put me over the edge. I blew my load up Shellie’s shit hole in no time after that. I pulled out of her rectum and saw it was still gaping open. Tim then went after her asshole, sucking and licking my cum from it.

Then it was just the two girls fucking. Shellie increased her speed and momentum as she rode Trina’s monstrous girl cock. For her part, Trina matched Shellie’s efforts with harder thrusts up into the pussy engulfing her dick. Now that Shellie’s mouth was free of cock, she became very vocal instead of just moaning.

“Yeah, baby! This big girl cock is filling my pussy! I can feel you all the way in past my cervix! I love it! You’re so good! So big!”

“Oh, yeah! Ride my girl cock, Shellie! Slam that ginger pussy on me! You’re so tight! So wet!”

They were pinching and squeezing each other’s tits as they started tongue kissing. Trina grabbed hold of Shellie’s ample ass cheeks and and started shoving Shellie down even harder on her cock as she increased her thrusts. Shellie broke the kiss and actually screamed as she hit her climax. Tim and were sitting back watching the spectacle before us. We could see my girlfriend’s juices flooding Trina’s belly and crotch as she had a squirting orgasm.


This must have triggered Trina’s own orgasm as she started yelling, “YES! YES! YES! I’M CUMMING TOO! I’M CUMMING IN YOUR TIGHT PUSSY, YOU FUCKING SLUT!”

Both women went limp, Shellie collapsed onto Trina’s chest. Trina wrapped her arms around the redhead, stroking her back and hair, kissing her sweetly, whispering in her ears. I couldn’t hear what was said, I just saw the contented smile on Shellie’s face. She then lifted herself up off Trina’s softening cock, and fell back on the bed.

“Whew! Holy hell! I’ve had a lot of DP’s but never a gang bang! Damn! Three big cocks too! And the biggest one is on a sexy girl! Thanks! All three of you! Thank you for this! I’ll always remember this feeling!”

Trina replied first, “You’re welcome, sweetie. And thank you for letting me be part of this. I’ll always remember it too. I’m sure these sweet boys will too. Right, boys?”

Tim and I answered simultaneously, “Oh, yeah! Absolutely! Thanks, ladies!”

After a short rest, a shower for each of us, and a bite to eat, the four of us went back to our fuck fest. We tried pretty much every combination we could think of. Tim and I did a 69 as the girls did the same. We fucked each other in the ass. The girls enjoyed watching us for a while as they rested. It was a great day, one of the best of my life.

Over the next couple years, the four of us fucked regularly, even when it was two or three of us. Tim and I even fucked without the girls there. I came to love cock and man ass as much as I did pussy and woman ass.

Eventually, Shellie and I broke up, but stayed friends, occasionally friends with benefits. I grew closer to Trina. She and Tim split, and with his blessing, we became a couple. I didn’t want her to hide who she was, and I came out to my family. They were more accepting of her than her family was of her.

Tim and I both continued to climb the corporate ladder. He eventually left the company we started at, while I became a manager there. He moved to another state, but we stayed friends. Trina and I married and bought a house. Tim was my best man, Shellie was Trina’s maid of honor.

After a couple years, Shellie ended up moving in with us. It was a sort of three-way marriage. When she and I were together, it was never a big love affair. But after she moved in with us, the three of us really came to love each other. She even bore two children, a girl fathered by me, and a boy fathered by Trina. We remain a loving family, raising our kids together.

Some endings are happy…

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By Dubya
#Bisexual #Group #Trans