I’d been with my girlfriend, Anne, for a long time, and I’d known that she was bisexual almost as long. We wanted to be an extremely open and kinky couple but we were only that way with each other. Outwardly we were very reserved.
We told ourselves that things would change when we went away to college, but they didn’t. And it was frustrating. Anne had a roommate that can safely be described as insane. She was older than we were and smoked an amazing amount of pot. She was also very open about sex. Almost obnoxiously so. She would leave her sex toys out in the main room, or leave porn playing on the TV even after she’d left. Anne was quietly determined to fuck her before graduation.
We had a party at the house one weekend. A ridiculous rager where we bought a keg, then sold drinks to anyone wanted to drop by until we made enough to buy another keg. The house was trashed, it was amazing. We partied, fell asleep, woke up and partied some more. Ultimately we ended up in Anne’s bedroom. The two of us, Jim, a friend we’d both known since elementary school, and the roommate. Both Jim and Anne were flirting with the roommate. But badly, neither was good at it. Sort of randomly, the roommate got up and wandered out.
“Damn.” Anne was pissed. Jim was startled.
“What?” Jim asked. Anne only blushed.
“Didn’t you notice?” I was very drunk when I said it. “Anne was trying to hook up with her.” Jim was stunned. Anne blushed even more and got embarrassed, then confrontational.
“What?” She demanded.
“I guess I just never thought of you sexually. I mean, I know that you and Greg…” he gestured lamely at me. “I mean, I’ve known you since before you had boobs.”
“Well, I’ve got them now.” Anne sort of thrust her chest out, in possibly the least sexy pose she could achieve. Jim made fun of her posing. Then he asked about her and the roommate and then her bisexuality. I was pretty quiet. Anne was unexpectedly forthcoming and after a while I noticed that Jim was very hard. He started to look uncomfortable and when a little wet spot started to appear on his pants he covered himself and stood to go to the bathroom.
“Are you going to jack off?” Anne asked him. It was extremely out of character and Jim was shocked into honesty.
“Yes”
“Can we watch?” She asked. Jim looked at me, startled.
It sounds harsh to say it but Jim was the most non-threatening man I’ve ever known. He was…fine. Not unattractive, but not anyone’s idea of hot. He was slim, pale and pretty nerdy. But he was also well kept and charming.
I shrugged my shoulders at his questioning glance.
“I’m not bi.” I told him. “But it would interesting to watch.” If anything he was more surprised than before. He stood there for a minute. It was obvious that his erection had disappeared.
“Not right now.” He said, sitting down again. He drank some more. Anne drank some more. I drank some more. “Maybe some time.” He was embarrassed. Anne was embarrassed. I was painfully horny.
“When her roommate comes back, let Anne have her.” I said. “Maybe she’ll let us watch.” Anne blushed. I went on. I talked about how badly Anne wanted to eat pussy and discover how a different girl tasted. Jim perked to attention. Anne was really embarrassed now and hiding her face a little. I was horny and drunk and I kept pushing. I talked about how I would sometime finger Anne and she would lick my fingers clean and we’d pretend it was from her girlfriend. Jim started shifting uncomfortably again. Anne noticed. She drank heavily for a while. Then got brave. I could tell she was pushing herself a little.
“Jim” She asked. “If I show you my boobs will you jack off for us?” She didn’t actually wait. I think she was scared to hesitate. She pulled off her shirt. She had on a plain bra, clearly not intended to be sexy. She quickly popped it off. Her breasts were amazing.
Jim stared. He was obviously rock hard. Precum was starting to soak his jeans. That pushed Anne out of her embarrassment. Once she was horny boundaries always seemed to disappear.
“Do you need more incentive?” She slid her hand into her jeans and pulled them out again. Her fingers were glistening. She slowly licked them clean. Jim moaned in arousal. She lay back on the bed popped the buttons on her pants and pulled them off along with her underwear. She always shaved a little landing strip.
“Show me your cock Jim.” He stood up and unzipped his pants. He glanced at me. He was horny. Very horny. But this was a huge step. He quickly pulled down his pants.
His cock was a surprise. It was hard and very long, longer than mine. But it was also very thin, about half the girth of mine. The head was very red, straining with arousal and soaked.
Standing, he started to stroke himself. He stared intently at Anne. She was slowly playing with her pussy. As his movements got more frantic hers slowed down. I was watching her face and it was clear she was thinking about something.
“Jim.” Her voice was soft, but commanding. Jim stopped stroking and looked at her face.
“Jim. We’ve known you a long time. We trust you completely, otherwise we would never have done this. I want to ask something but I’m really embarrassed.”
Jim was panting. He had been close. His cock started to deflate in his hand.
“Will you fuck me up the ass?”
Utter silence. Anne covered herself with a pillow and looked down. She glanced up after the silence became uncomfortable.
“I’ve only had sex with Greg. I would like to try another man. But my pussy is his alone. Will you fuck my ass?” I was a little startled. We’d talked about her fucking another man, but we had never said that her pussy was off limits. Her eyes were fixed on his cock and I realized. We’d tried anal before but, no matter how much she wanted to, she had never enjoyed it. It was always painful. Jim’s narrow cock would be easier, but she didn’t want to hurt his feelings.
Jim looked at me and I looked back. I was excited, but didn’t know what to say.
“Jim.” Anne’s voice was more confident. “It’s my ass and I want to share it with you. Will you take my anal virginity?” That was a lie, but it seemed to push him over the edge. His cock was harder than it had ever been.
“Yes.” He was extremely excited.
Anne smoothed out the bed and slowly rolled on to her stomach. Her ass was as amazing as her breasts has been. She pushed pillows under her hips until her ass was raised. She buried her face in the bed, simultaneously excited and wanting to hide in embarrassment. I was the only one who had ever seen her ass. Jim and I stared. She reached back and slowly spread her cheeks. Her asshole was glorious.
“Greg?” Her voice was extremely muffled. She wouldn’t lift her head. “Can you get the lube?” I got the bottle off her nightstand and slowly spread the lube into her ass. I slid a single finger deep into her. She grunted. A visceral noise. She was burning hot inside. I always loved the way it felt inside her ass, like a raging inferno. I couldn’t help myself and started to fuck her ass with my finger. She thrust back for a moment, then stopped me with her hand.
“No.” She still wouldn’t look up. “Save it for Jim.” I pulled out and stepped back. Jim looked at me. He eyes were feverish. He stepped forward. I held Anne open for him and he slide in. Instantly he went deeper than I ever could. Anne yelped in pain and he stopped. She held up a hand.
“Give me a second.” He held perfectly still. She lay beneath him, panting hard. Her breath slowed after a minute. “OK. But slowly.”
Jim slowly pulled out, almost all the way, then slowly pushed in again. Holding her open I saw the puckered skin of her asshole tighten as he moved. Anne made soft noises.
He began to pick up speed and Anne began to push back against him. I slid my fingers around to her clit and made small circles. Her hips began to buck. Jim moved faster. He was gasping now, holding her hips tightly. Every muscle in his body was straining. He was desperate to fuck but still holding back, afraid of hurting her.
Her pussy was soaked and I rubbed harder against her clit. She gasped and I rubbed harder. She gasped again and I rubbed faster. Her body seized and began to convulse, throwing off Jim’s rhythm. Every muscle in her body clenched, relaxed and clenched again.
“Do it. Hard.” She shouted into the pillow. Jim lost all semblance of control. He grabbed her hips and slammed forward, driving her forward on to the bed, wrenching my fingers away from her pussy. He seemed to go wild against her. He tensed.
“Where do you want me to come?” He asked, between clenched teeth. She lifted her head for the first time and looked over her shoulders.
“My ass. Greg wants to see you fill my ass with cum.” I did. At that moment I wanted it more than I’d ever wanted anything. Jim surged forward and exploded. He pumped into her, hard. Over and over again. Finally he finished. Slowly he pulled out. Anne gasped.
I didn’t know what came over me. The second Jim stepped away I moved behind Anne. I grabbed her cheeks roughly and spread them apart. As far apart as they would go. Cum dribbled out of her. It was the most erotic thing I’d ever seen.
I quickly undid my pants. Not even bothering to take then off. I rammed into her ravaged ass. Even dripping with lube and cum, stretched by fucking Jim, she was still too tight. She shouted in pain. I was beyond caring. I fucked her hard.
I grabbed a fistful of her hair.
“Say his name.” I demand.
“Jim.”
“Again.”
“Jim!”
“Say his name.” I pulled back on her hair. Her head came up and her body slammed against me.
“JIM!” I exploded. Every fiber of my being emptied into her. For a moment it felt like I transcended this mortal plane.
Eventually I came back to myself. I slid out of her and lay on the bed. Jim was beside me. He had been watching the brutal fucking and jacking off. He came softly on her back.
Eventually Anne rolled over and lay there, legs splayed. A smear of cum and lube around her crotch. Utterly unashamed. Absolutely beautiful. She was gorgeous.
She never did fuck that roommate though.
[The Chronology of Anne](https://old.reddit.com/user/LordUnderTheMountain/comments/ue7sn8/the_chronology_of_anne/?ref=share&ref_source=link)
Source: reddit.com/r/eroticliterature/comments/uf082e/the_wrong_threesome_mfm