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Roommate’s Girlfriend Has A Surprise

3601 words | 17 |4.87

My roomie’s flirty girlfriend has something extra in store for me…

My name is Mark. I’m in my late 20’s, working my way up the corporate ladder after completing college. To help keep down costs, I moved in with a coworker, Tim. We share a 2 bedroom apartment in the city where we work. It’s in walking distance from our office, so we don’t have to worry about transportation, another way to save money.

Tim and I don’t work in the same department, so we’re not all over each other 24 hours a day. We can commiserate with each other about the company, and keep up with gossip, but not be in each other’s way all the time. We’re friends outside of work now, but not best friends. We work out together in our building’s gym and have a beer together occasionally, but we have our own social circles. It’s been a great situation so far.

We’re a lot alike in many ways, being the same age and in the same field of work, but different in others. We’re both fit, Tim being pretty tall at 6’3″, and pretty slim, while I’m 6′ and more stocky. He played basketball in school, whereas I played baseball and football. Tim has dark hair and eyes, and I have sandy blonde hair with hazel eyes. We’re both considered good looking.

We both have girlfriends. My girl’s name is Shellie. She’s a long-haired ginger hottie, standing about 5’5″ with 38DD tits and a nice round ass to go with them. She fucks like a wildcat and isn’t afraid to try anything. We hadn’t yet had a threesome before the events I’m about to describe happened, but I knew she was bi and open to it.

Tim’s girlfriend is Katrina, or Trina as she prefers to be called. She’s a slim, petite blonde with a pixie haircut and perky titties to match her pert ass. She’s a real cutie, and flirty too, but I had always thought there was something different about her. Maybe it was her voice or just the way she acted, but she was definitely different.

The apartment Tim and I shared was spacious, with the bedrooms situated on either side of the living room and kitchen/dining area with a half bath inside the entrance foyer. Both bedrooms had en suite bathrooms, so we didn’t interfere with each other much.

One Saturday night I was home alone. Shellie had plans with friends, and Tim was out with his buddies. I decided to just chill and enjoy some peace and quiet for a change, when there was a knock on the door. I opened it to find Trina standing there.

“Hi, Mark,” she said in that slightly husky yet sexy voice of hers. “I know Tim is out. My roommates are having a party but I just want to chill for a change. Is it okay if I hang out here? I texted Tim and he said it’s okay. I can just hang out in his room, you won’t even know I’m here.”

“Of course. Come on in, Trina,” I replied. “You don’t have to hide in Tim’s room. You can hang out with me out here. We can watch a movie and have some wine if you’d like. I have a pizza on the way.”

She let out a little squeal and said with a flirty tone, “Oooo, a little Netflix and chill! I love it.”

I took her coat and she went to Tim’s room, closing the door. A few minutes later, she emerged wearing sweatpants that hung low on her hips, and a tight crop-top t-shirt that showed she obviously wasn’t wearing a bra. The nipples of her perky B cups were hard and stood out. If I didn’t know any better, I’d think she had something in mind.

“I hope you don’t mind that I slipped into something more comfortable, as the cliche says,” she giggled.

“Not at all,” I replied with a grin.

Just then the door buzzer sounded, announcing the arrival of the pizza. I paid the delivery guy, plated up some slices, and poured a couple glasses of wine. I brought them out to the living room where Trina was scrolling through movies to watch. Tim and I each had TV’s in our respective rooms, but we had a nice wide-screen in the living room where we usually watched sports.

“Do you mind something… romantic, Mark? Or would prefer some… action… movie,” Trina asked with a sly smirk.

I smirked back and replied, “Romantic is good. Maybe some action later.” I figured two could play this game. Like I said, Shellie is a hottie that is a firecracker in bed, but I’d be lying if I said my eye didn’t wander occasionally. Shellie was cool with it as her eye was known to wander occasionally too.

Trina picked some ensemble love story that had a couple LGBTQ subplots. Amongst the straight couples in the movie were a lesbian couple and a man with a trans girlfriend.

“Is this okay, Mark? If the queer stuff bothers you, I understand. We can watch something different.”

“No, no, it’s fine. I’m a modern guy. I’m good with people being who they are.”

I wasn’t lying. I’ve never been inclined toward homosexuality or bisexuality, but I’m certainly not bothered by it. I was being more tolerant of the movie being a rom-com than it having queer content; I do prefer action or comedy movies.

Trina shocked me when she leaned over to peck me on the cheek. I could feel my cock starting to stir. She rubbed the spot on my cheek that she had kissed, I guess to get the lipstick off. She smiled and almost whispered, “You’re sweet… and cute.”

My cock responded more. I wondered if she noticed it through my loose shorts. A little bit of conscience crept into my mind then. This was my roommate’s girlfriend, I didn’t want to screw up our situation by screwing her. But damn! She was obviously coming on to me! And she was sexy as hell! Maybe she was just messing with me, I thought. I decided to see how far things would go.

After finishing the movie, more pizza, more wine, and some chit-chat, Trina announced that she was going to take a shower. I cleaned up while she was gone. After I finished, I sat back on the couch and scrolled through the TV menu, hoping Trina would come back out in something even more comfortable. She didn’t disappoint.

Tim’s bedroom door opened, and there she stood, wrapped in a towel while drying her hair with another one. But the towel was wrapped around her waist like a guy would do, exposing her perky tits and luscious pink nipples.

“Oh! You’re still up! Sorry, sweetie, I thought you might have gone to bed.”

She gave me a smile that let me know that that wasn’t the case. She also made no move to cover her tits. She turned and went back to the bedroom, leaving the door ajar. I took this as a signal, and followed her in. She was facing away from me, but looked over her shoulder with a look of longing, biting her lower lip. That made me weak in the knees and my cock hard as a rock.

She let the towel around her waist drop, exposing her perfect, pale white ass. She held the towel in front of her crotch as she turned to me. I took her in my arms and kissed her tenderly.

“Mark, before we go any further, you have to know something…”

“What? Is it about Tim? He doesn’t have to know. But I need you now…”

“No, that’s not it. Tim and I have an open relationship. He’s already told me it’s okay if we fuck, but…”


At that, she looked down and let the towel drop. I was astounded at what I saw! Instead of a tight, little pussy, Trina was sporting a huge cock!

She looked back up at me with what I can only describe as fear in her eyes. She bit her lower lip again, this time with trepidation instead of longing. I just stood there aghast. My mind was reeling! I had always thought of myself as open-minded although I never felt any curiosity about bisexuality. But here I was with this beautiful creature offering herself to me.


I responded by grabbing her girl cock and pulling her into a passionate kiss, tongues entwined, probing. I stroked her cock to full hardness, the first one I had ever touched besides my own. It felt incredible! My other hand found her ass. It was soft yet firm, just the way a girl’s ass should feel.

“I’m so glad you’re not freaked out. I didn’t know if you were into t-girls or not, but I’ve been wanting you since you moved in.”

“I… I’ve never been with a t-girl or even another guy before, never even thought of it, but I want you too!”

I led her to my room, stripping down once in there. She sat on the edge of the bed as I approached her. She looked up at me with doe eyes as she reached for my 7.5 inch uncut cock. She never broke eye contact as she stroked my erection, then took it in her mouth.

She was an expert at giving head, licking, sucking, nibbling, stroking my crown, shaft, and balls. All those sensations combined with the eye contact drove me crazy! I could have cum right then, but I wanted to hold off. I wanted to explore this new world that had opened up to me. I pulled my cock out of Trina’s luscious mouth, then bent to kiss her again.

I got on the bed and we embraced, rolling around in the throes of passion as our tongues explored each other’s mouths. I took hold of her cock as she took hold of mine. We jerked each other while we continued to kiss. Then I couldn’t help myself anymore, I needed to suck her cock!

I kissed my way down her neck to her chest. I squeezed her little titties, finding they were real, not implants. I sucked her nipples, which were surprisingly large. I bit them, flicked my tongue over them lightly, sucked hard, back and forth to each tasty morsel. She was going wild, pushing my head down.

I traced my way down to her navel with my tongue. I circled it and poked my tongue in it, eliciting squeals of delight from her sexy mouth. She pushed harder on my head, encouraging me to move down to her cock. I finally got there.

My cock is fairly sizable at 7.5 inches and very girthy, but hers was even bigger. There should be no way that a person so petite should have a cock almost 9 inches! But there it was, hard as a rock, cut, and completely hairless. No stubble was apparent so she must wax instead of shave.

I was mesmerized! It was big and beautiful and I wanted it in my mouth! I wasn’t sure what my plan of attack was but I knew what I liked done to mine. I started by licking around the crown and down the shaft as I stroked it. Finally, I worked up the nerve to take it in my mouth. Thankfully it didn’t have as much girth as mine.

I took in as much as I could, going slowly. I got about halfway down when I started gagging. Trina coached me, telling me to breathe through my nose and not worry about going all the way down, just jerk what I couldn’t take. I did as she told me and I seemed to be doing well from the reaction she gave. She was moaning and talking dirty as she wrapped her fingers in my hair.

She pulled her legs up to her chest, exposing the pucker of her hairless asshole. It looked tight and inviting.

“Please, Mark! Please eat my pussy! Eat my boy pussy! Please!”

Boy pussy and girl cock were all new to me but I was happy to eat both! I had eaten ass many times in my day, Shellie particularly loved it, so I had no problem eating this one. I did eat it like a pussy too, licking all around it, flicking my tongue lightly across it, shoving my tongue as deep as it would go into it. She squealed and squirmed as she shoved my face deeper into her ass crack.

“Baby, I’m getting close to cumming! Do you want me to cum in your mouth?”

I enthusiastically replied, “Yes! Fuck yeah!”

I took her cock back in my mouth as a torrent of creamy spunk shot out of it, filling my mouth. She was still shooting when I took my mouth off her monster member, getting all over my face and hair. I’d never even tasted my own cum before but I absolutely loved it! And the texture of it in my mouth felt amazing! This may have been my first time sucking a cock but it certainly wouldn’t be my last!

“Fuck, baby! Have you sucked cock before,” Trina asked breathlessly. Her chest was heaving like she had just run a marathon.

“No. I swear. Never.”

“Well, sweetie, you are a fucking natural!”

She pulled me up to her and licked all her cum off my face before kissing me again. My cock was throbbing as she again took hold of it.

“How would you like to fuck my tight, little pussy, baby? I want to feel your big cock stretching my hole!”

I didn’t have to be asked twice. I kept a bottle of lube in my nightstand since Shellie loved a good ass fuck. I retrieved it and greased us both up. Trina held legs back again like she had when I ate her pussy. She looked so damn sexy in that position, her pussy exposed as her half hard cock laid against her belly. I never thought something like this, someone like this could turn me on so much.

I lined my raging hard cock up with the puckered rosebud of her oh so pink asshole. I pressed the head of my dick against her sphincter and pushed. It took me in easily. This was a well used hole, after all. She encouraged me to put it all the way in, wrapping her legs around me and pushing her heels into my ass.

I bottomed out in Trina’s pussy ass and held there a moment before starting to thrust in and out with animal lust. This t-girl definitely wasn’t a virgin, but she was still tight as hell! I pumped and pumped and pumped. Damn! She felt so good!

Trina wrapped her arms around my neck and kissed me again, her hot, talented tongue danced in my mouth. She alternated between the kisses and whispering in my ear about how much she loved the way I fucked her, how good my cock felt in her pussy, how long she had wanted this. She kissed and bit all over my neck and shoulders and chest as I pounded her relentlessly. She sucked my nipples, which drives me wild.

That put me over the top and I grunted, “I’m cumming, baby! I’m cumming in your pussy, Trina!”

“Yes! Yes! Fill my pussy with your cum, baby! Do it! You’ve got my girl cock all hard again! That’s how good you are! Fuck me! Cum in me!”

I was very vocal as I climaxed, yelling out her name, and a lot of other unintelligible nonsense. I don’t think I had ever cum so hard in my life! My toes curled, my body quivered, my eyes rolled back in my head. I was drained, spent. I went limp and collapsed on top of Trina’s petite body. She didn’t seem to mind. Her legs were still wrapped around my waist, my softening cock still in her ass. She ran her fingers through my hair as she covered my face with light kisses.

“Are you all right, sweetie?”

“I’ve never experienced anything like this, Trina! It was… amazing! You! YOU were amazing! Are amazing! Holy fuck! I can’t believe I just sucked a cock, a girl cock, and fucked a pussy ass! You are so beautiful! So sexy!”

She giggled and said, “Well, thanks, stud. You’re pretty sexy yourself. You know, there’s one more line you haven’t crossed. Are you up for it?”

I felt her push her hard cock against my belly. This had definitely not occurred to me. I wasn’t sure about that. Getting fucked in the ass? With a cock that big?

“Ummm… I don’t know…”

“Come on, big boy. You can take it. You wouldn’t be the first virgin I broke in. I’ll be gentle. Whadda ya say?”

I finally relented. She told me to get up and follow her. We went to Tim’s bathroom where she pulled out a contraption with a nozzle and squeeze bulb. She explained that it was an anal douche. She filled it with warm, soapy water, lubed up the nozzle, then stuck it in my ass as I bent over the sink. The water filled me cavity. It felt strange but not unpleasant.

Trina instructed me to sit on the toilet and empty myself. After I did, we repeated the process. After drying off, we went back to my room. I asked what position she wanted me in.

“Lie on your back, sweetie. I want to see your face as I fuck you the first time.”

I got on the bed, lied on my back, and pulled my legs back like she had done.

“Well, look at you! You are ready, aren’t you?”

She grabbed my bottle of lube and greased my virgin asshole, then stuck two of her delicate looking fingers up in it. Then she greased up her big fuck stick and lined it up with my boy pussy. She pressed the head against the untested ring of my tender asshole.

“You ready, baby?”

“As ready I’ll ever be!”

She told me to bear down like I was pooping as she gently pushed. Suddenly the head of her girl cock popped through the sphincter of my boy pussy and she was in.

“Hey! You’re no longer a virgin, baby boy! Are you ready for more?”

I gritted my teeth and said, “Do it!”

She only had about 2 inches in, then slowly pushed in more. She told me to tell her when to stop. I couldn’t believe how wonderful it felt! I was so full, so fulfilled! I didn’t want her to stop! This was my last frontier! My last taboo! I was getting fucked in the ass! By a girl! A girl with a real cock, not a dildo!

“Keep going! Keep going! Wait! Stop,” I exclaimed when I felt like I couldn’t take any more.

“Would you look at that! I can’t go any more, baby, I’m all the way in! I guess you can take it all!”

I was astounded! My first time getting my ass reamed, and by a monster cock, and I took it all! I realized then that I had been missing out my whole life on this wonderful way of pleasure!

“Are you ready for me to start really fucking you now, baby,” she asked with that husky voice that I was coming to love hearing.

“Yes, baby! Do it! Fuck me!”

She started thrusting gently, in and out, in and out, whispering words of encouragement.

“You look so cute like this. I’m glad we did it in this position this time. I’m glad I got to see your face as my cock entered you.”

In response, I wrapped my legs and arms around her, pulling her face down to mine for another spit swapping kiss. She fucked me gently like this for a while before pushing herself up on her arms and thrusting harder. I could feel the head of her dick bouncing off my prostate. This made my dick get hard again. She grabbed the lube and poured some on my dick, then jerked it for me as she fucked me.

She picked up speed and momentum as she continued her assault on my bowels. I was in ecstasy! My head was reeling in a fog of bliss! I was getting close to blowing my load again and I told her.

“I’m close too, baby! Let’s cum together! Come on! Cum for mama!”

I let loose then. I couldn’t believe I could cum that hard again after having already had a massive orgasm. My ass muscles clenched down on Trina’s girl cock as she emptied her second load of the night inside me. Like I had when I came inside her, she went limp and collapsed on top of me. I held her and stroked her hair, kissing her face and neck. She seemed dazed.

When she had regained her composure, she turned to me and smiled sweetly, then said, “You were the best virgin I ever had, darling!”

Then she snuggled into me and we both fell asleep. We were in the same position come morning when we were awakened by someone talking. I opened my eyes to find Tim and Shellie standing over us, smiling. As the sleep left my eyes and I was able to focus, I saw that they were both also nude. I nudged Trina awake.

“Looks like you too had fun,” Tim said, still smiling. “Ready to have some more?”

What happened next will be in part two…

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  • Reply Bob ID:1dt2wzqeekjx

    Now that’s the kind of roommate to have. Who would know that he had a trans gurlfriend!!! Nice way to get introduced to a big cock on a trans!!! I’d love to be a roommate with those two.

    I hop you have a number of parts on this series. I love masturbating as I enjoy the reading.

    Love, sucks and fucks,

    [email protected]


  • Reply Tyra ID:bhr2s6zr9

    Banging story, who’s down with me should text ( [email protected]) let’s get freaky

    • PrettyToes ID:zdbeleyd3

      @Tyra I refuse to chat or have anything to do with google. They used to be my favorite chat, mail, voice, photos, etc. I sent a person a draft of one of my stories and google intercepted and refused to send it indicating that it was inappropriate. That should have been a red flag for me as I found that they monitor every platform. Your email, phone, chats, photos, location, eating, driving and shopping habits, basically everything that you do is monitored and stored by Google forever.

      Last year I visited a family nudist site and took some SS’s because I was interested in joining. I uploaded them to my G-drive and the next day I was locked out of my account citing that I am a child abuser.

      Jan 16 of this year I received a phone call indicating that the food I ordered was outside in front of my truck. So, I went outside to look and all of a sudden 9 police units with 12 detectives drive into my cull de sac with their lights on. The lead approaches and handcuffs telling me he has a warrant to search my home. By the police presence, you’d think that I was operating a child trafficking ring. They tossed my house, collected two Chromebook’s, two iPhones and an iPad.

      I was embarrassed and humiliated before all of my neighbors. The warrant was sealed for thirty days, meaning I was not told the circumstances of the search.

      After 30 days I read the warrant affidavit, and I couldn’t believe what I was reading. Google reported me in possession of child pornography labeling me a child abuser, provided them with my IP address, and all of the meta data for the SS’s.

      So, I now have Proton mail and storage, a VPN, and Session’s chat platform. I would suggest you reconsider your relationship with Google and take the same precautions. Download the sessions app and I will chat and get freaky with you.

      If charged it will cost me $7500 to retain an attorney and I am facing jail time of up to 5 years

      Sessions ID: 05ffae827a1e4f0743bf0cc7c1dc0220cf1f3fe978ea8ce68bd0bb4c89585cfd3a

    • PrettyToes ID:14grun306ib


      I refuse to chat or have anything to do with google. They were my favorite chat, email, voice, photos, etc. I sent a person a draft of one of my stories and google intercepted and refused to send it indicating that it was inappropriate. That should have been a red flag for me as I later found that they monitor everything. Your email, phone, chats, photos, location, eating, driving and shopping habits. Basically, everything that you do is monitored and stored by Google forever.

      Last year I visited a family nudist site and took some SSs because I was interested in joining. I uploaded them to my Google drive and the next day I found my account had been locked citing that I was a child abuser. I lost access to everything!

      On Jan 16 of this year, I went outside and all of a sudden 9 police units with 12 detectives drove into my cull de sac with their lights on. The lead handcuffs me saying he has a warrant to search my home. With the amount of police, you’d think I was operating a child trafficking ring. They tossed my house, collected two Chromebook’s, two iPhones and an iPad.

      I was embarrassed and humiliated before all of my neighbors. The warrant was sealed for thirty days, meaning I was not told the circumstances of the search.

      After thirty days I read it, and I couldn’t believe it. Google reported me in possession of child pornography labeling me a child abuser, provided them with my IP address, and all of the meta data for the SSs.

      I switched to Proton mail and storage, a VPN, and Session’s chat. My suggestion to you and everyone else is to get rid of Google. Download the sessions app and I will chat and get freaky with you.

      It cost me $2500 already and if charged it will cost me another $5000 to retain an attorney and if found guilty, I am facing jail time of up to 5 years for storing SSs of underage nudists playing volleyball.

      Session ID:


    • Dubya ID:7l5pq5d8qyu

      Tyra, do have the Session app?

  • Reply Bolou ID:53dpnkj41

    Great story, made me explode thinking about that huge cock smashing his virgin ass! 😮

    • Dubya ID:7l5pq5d8qyu

      I’m glad you enjoyed!

  • Reply BRITNEY ID:1df0k80uvhff

    Oh Dubya your story really turned me on !! Now I feel like a cat in heat !! Thanks for the turn on !! Britney

    • Dubya ID:1cyit7b0r2hz

      Britney, I love hearing that from a hot woman like you!

  • Reply Empty balls guy ID:2kyhpc18rd

    So did my landlord s wife last night. She’s 47 and got cerebral palsy and in a wheelchair last night her husband Mark had cards night we got drunk and then started sniffing loads of coke and then he suddenly said that he wanted our help. So he called Sally his wife she came in and he told her was horny she started sucking him off and then he said gangbang her

    • Dubya ID:1cyit7b0r2hz

      Sounds like a fun time! You should write a story about it.

  • Reply hammer ID:16m9jekyf6ns

    Love this story

    • Dubya ID:1cyit7b0r2hz

      Thanks! Glad you enjoyed!

  • Reply Jack45 ID:19u48dkzj

    EXCELLENT Thanks

    • Dubya ID:7l5pq5d8qyu

      Thank you!

  • Reply Jarrbo ID:1ck8ojvmnlmi

    I DEFINITELY feel like my name is Mark. Is there any Trina around here?😊😊😊 Because I would love to recreate this great scenario in real life…😋😋😋

    • Dubya ID:7l5pq5d8qyu

      You are my number one fan!