Cuckold arrangement leads to girlfriend making me question myself (MF, Cuckold, Gay roleplay)

>So I told Dave that I was thinking about letting you watch and he had a few demands. That you don’t talk, and that whatever he says goes. And no matter what, you can’t walk out. Would you do that?

She said as she tugged gently at me with her hand up the leg of my shorts. I got hard just thinking about it.

Dave was her ex, her former dom and she had a deal with him they could fuck whenever he wanted. She lied about it the first few times when we first started dating. She claimed to be going home to her parents house but one of my friends working at a bar across town saw her and tipped me off. When I confronted her she confessed to me and for some reason I begged her to stay with me. Lisa was probably the hottest girl I’d ever date in my life and I needed to keep it going. And we did so on the arrangement that if she needed to see someone else for sex she could.

Jen’s strapon part 2 (mf pegging, mm gay)

[part 1](https://www.reddit.com/r/eroticliterature/comments/l3s84j/jens_strapon_pegging_mf/)

Jen got behind me on the couch and wrapped her legs around me and opened her phone and told me we were going to make some ads. (This was in the days of craigslist).

She slipped her hand into my shorts and felt my small erection.

“Which one should we start with?” She moved her hand to my taint and pressed towards my ass. I told her either. “Here you write it and I’ll encourage you”.

She handed me her phone and moved her other hand through my legs to my ass and used her other one to take my dick out. She was grinding me a little from behind and kissing my neck and ears.

I began to write. “Hot girl seeks cute guy to peg”.

“In front of her bitch boyfriend” she whispered. I edited the title.

“What do you want him to look like?” I asked. She told me it was my fantasy and to write what I wanted.

“Athletic soccer type body, clean, and clean shaven, must have muscles and look good naked, decent cock, cut”.

Jen’s strapon (pegging mf)

Jen and I met at a bar and were just getting to know each other. She was tall and a little muscular from being on the rowing and swim teams, but other than that she was an average looking girl with big tits and a filthy mouth.

Being in our early twenties we always met at bars and went to one of our apartments to fuck. She had made a bunch of strapon jokes and it had me interested but I didn’t want to volunteer or anything like that. I played it cool.

But one night after a few drinks we were back at my place and she was blowing me and then she licked my ass.

“Holy shit”. I gasped. “Wow”

“There’s a lot more where that came from” and she went full on rimming me for a few minutes. It was a weird feeling as a dude, not the butt licking. That felt great. But laying there like a girl getting my ass licked. Then she lifted my legs and started to hump me with her pussy.

After the sword fight (part 3 the end) (cuckold, bi, MF, MMF, MM, Pegging)

You don’t need to read the other two for this story to work but you may like them. This is the end of the series.

[Part one](https://www.reddit.com/r/eroticliterature/comments/ku2pl1/sword_fight_mfmmf_bi_cuckold/)

[part two](https://www.reddit.com/r/eroticliterature/comments/l01pez/after_the_sword_fight_part_2_mf_mmf_bi_cuckold/)

For the last week, my girlfriend Alissa has been blowing my roommate Kevin anytime he asked for it. They had an agreement they wouldn’t have sex without my consent and me being present. It felt like my life was spiraling out of control and I was losing her and myself.

Both times I was involved I was humiliated, made to suck cock and took him in my ass. I hated it. But I was jerking off more than I ever have. I couldn’t stop thinking about taking cock.

Alissa came over early one afternoon. She was wearing short mesh shorts and a tiny white tshirt that showed her flat and bare midriff and her underboob was very close to showing. She had a full b cup with perky tits, her short hair was up with some clips and wore her librarian glasses. It looked like an outfit she should wear to bed and not around town, but whatever. She was my girlfriend, kind of.

After the sword fight (part 2) (mf mmf bi cuckold)

[Part 1](https://www.reddit.com/r/eroticliterature/comments/ku2pl1/sword_fight_mfmmf_bi_cuckold/) – not required reading for this story

I woke up to my girlfriend spooning me from behind. She was running her hands down my stomach and grinding into me.

I started pushing back into her and when she knew I was awake put her hand down my shorts and pulled me out.

The morning light was coming through the shades as she moved the sheets and took me in her mouth.

Alissa looked like a mess. She had deep bags under her eyes and had a big hickey on her neck. She was wearing Kevin’s 76ers basketball jersey so I could see her side boobs which was pretty hot as she furiously sucked on me.

As this was happening, everything from last night came rushing back into my head. I still couldn’t believe how far things went last night and how they humiliated me. I was hoping I was just waking up from a bad dream but it was very real. My girlfriend picked my roommate, specifically his cock over me. Not only that, he fucked me, figuratively and literally.

Sword fight – (MF/MMF bi cuckold)

Alissa was a little flirty that night. She showed up to our college party house with her tight white tshirt ripped down the middle so her cleavage was out all night. Alissa was about 5 foot 2 and skinny. She wore dark black glasses that gave her a Librarian look. We were both 19 and I was living with a few buds at a college house in Maryland.

She didn’t wear a bra and had small boobs and short hair and we had been seeing each other for six months or so.

She was especially flirty with my friends that night but I never thought twice as she always came upstairs with me. She nudged me to go upstairs with her and I followed obediently.

Instead of going into my room, she pulled me into the single bathroom on the second floor. It was kind of naughty because we still had a handful of people downstairs drinking and carrying on.

She turned the shower on and got me undressed told me to get in. Alissa quickly stripped and joined me. I reached out of the shower and locked the door when she got on her knees.