Your erotic stories

Jason is my jack-off buddy. We had dated for a little while, when we were both seniors in high school, but it hadn’t worked out. I hadn’t seen him for years, and then he moved to the city. He looked me up, and we discovered that we were still really good friends. We still fool around once in a while, but mostly we just masturbate together. Once every couple weeks, sometimes more often, sometimes less, I go over to his apartment, and we watch porn, drink beer, and masturbate.

It’s a pretty good arrangement. Its fun watching him handle his sizeable cock, watching his balls tighten and his fist blur before he shoots off. I know he likes watching me, and I enjoy putting on a show for him, fucking myself deeply with a dildo while strumming my clit and twisting my nipples.

Once a month we get together to play scrabble. We are both really competitive, especially with each other. We’re both good at scrabble, but I win a little more often than him. We play best two out of three and the loser has to accept a punishment decided on before the game. The penalties started out pretty mild (for us): the loser would have to masturbate while the winner watched, and couldn’t come until she (or he) said. Or the loser had to give the winner head. Stuff like that.

As the months passed, the stakes got higher, the penalties stiffer. Jason suggested that the loser have to masturbate with a dildo in their ass. I won that night. I got the big blue dildo out of my backpack. Jason brought out a small bottle of Astroglide. He got naked while I lubed up the dildo. His cock was rigid as he bent over the couch, presenting his tight little ass to me. “Go slowly” he said.

I went slowly, as gently as I could. I didn’t want to hurt him; I wanted him to enjoy this as much as I was going to. I spread his cute butt cheeks and pressed the dildo against his tiny puckered hole. He groaned and pressed back against me, arching his back. His asshole opened up, swallowing the tip of the plastic cock. He looked so sexy like that. I was incredibly turned on at that point.

“More” he whispered. I pushed my toy deeper inside him. “Fuck, that feels incredible” he said. It was almost completely inside him now. I couldn’t wait; I pulled down my pants and let my free hand find my engorged clit. I was soaking. His little brown hole was stretched wide, his balls were drawn in tight, his eyes closed in rapture. I started fucking him, gently at first, and then as he started to hump back, I fucked his ass harder and harder. He was stroking his cock, and I knew neither of us would last much longer. I was burying the dildo up his ass all the way to the base, then pulling it out and slamming it back in. I couldn’t believe how rough I was being, and how much he liked it. I lost track of time as I fucked him like that, bent over in front of me. When he came, squirting gob after gob of hot semen, my cunt spasmed, and I fell onto him, still fucking him as I came, wave after shattering wave of orgasm. It was great.

The next month, I suggested that the winner pee in the losers’ mouth. Jason agreed to the stakes. It was close; we each won a game, and then I eked out a win in the third game. We stripped, and Jason lay down on his back in the bathtub. I squatted over his face. We both got the giggles. At first, my bladder was shy, but I had had a beer and a couple glasses of water, and it didn’t take long. I let go with a long clear stream right onto his face. I managed to direct the stream into his open mouth, and he took it all. When I was done, he licked my pussy clean. We were both so turned on we masturbated right there in the tub, me squatting over his face, with an excellent view of his cock and balls.

The next month, his sisters’ young friend, Jill, was in town. She was 18, a senior in high school, and thinking about going to NYU next year. I knew Jill was staying at Jason’s’ apartment that week. I asked him if we should maybe play our monthly tournament at my place, but he said not to worry about it. “Come on over.” He said.

The three of us had had lunch earlier that week. She was a cutie, tall and slim, with lots of dark curly hair and enchanting brown eyes. She seemed all girly and innocence. I admit that I had wondered what was under her faded blue jeans, her oversized sweat shirt. Now I was surprised to see her sitting at the table with Jason next to the scrabble set up. They were in the middle of conversation, and Jason had just said something that made her laugh uproariously. She had a great laugh; I believe you can tell a lot about someone by the way they laugh.

I had expected Jason to send Jill out on the town while we played, but to my surprise, he started racking the tiles right away. I wondered what he was up to.

“What should the loser get this time Jason?” I asked him pointedly.

“Well” he drawled “I thought that this time, the loser has to masturbate while Jill watches. What do you think of that?”

I looked over at Jill, who was grinning. “Oh that’s fine by me” I said, “But what does Jill think of that?”

Jill said “Oh that sounds fine to me.” So that was that.

Jason won the first game easily. He drew great letters; I couldn’t find a word to save my life. I didn’t mind the idea of the penalty… Jill could watch me masturbate any day she wanted; but I was proud and competitive and not about to lose if I could help it.

The next game was close. I was behind for most of the game, but I rallied near the end, and sealed it by finishing with “qat” on a triple letter score. I won by 20 points.

As we cleared the board and scrambled the tiles, I asked Jill who she wanted to win.

“It doesn’t matter to me.” She said and gave me her sweetest smile.

It was a very close game. The room was silent; Jason and I were both concentrating intensely. As I have said before, both of us are highly competitive.

The score was 296 to 290, and I was behind. Using my last tiles, I played “rat” for three points. Jason’s last letter was an “n”, worth one point. Add one to my score, subtract one from his and the final tally was 294 for me, 295 for him.

“Looks like we have a loser.” Jason deadpanned. Jill only smiled a secret little smile. “Shall we move to the couch?”

I was pissed that I had lost, but that doesn’t mean I wasn’t looking forward to getting naked for young Jill. On the contrary, my nipples were already pointy hard with the idea.

Jason went to the kitchen to get beers for each of us, while I stripped down to my bra and panties. I sat on the couch, thighs apart, while Jill knelt on the floor in front of me, watching me with the intensity of a cat watching a fish tank.

I could almost feel her breath on my inner thighs, and it made me super horny. I traced my slit through my panties, feeling the soft material press against my wetness. My clit was already throbbing. I slid my hand inside my bra cup, tweaking my nipple.

“Show me your tits.” Jill whispered. I was happy to comply. I unsnapped my bra, setting my breasts free. They’re not all that big (I wear a 34b), but I don’t think Jill minded. I loved being on display like that. Jason had come back, and handed me an open beer. I took a long cool drink, and then slid my fingers down inside my blue panties, dipping them in my wetness and lazily circling my clit.

“No fair” moaned Jill “I want to see!” I loved teasing her, but the time for teasing was rapidly coming to an end. I rolled my underwear off and spread my wet cunt wide.

“Do you like it?” I asked.

“Oh yes.” She replied. I pulled back the little hood, displaying my red hot clit for her. I desperately wanted to feel her tongue on my sex, but a deal was a deal. “Finger yourself for me.” She said.

I did. I spread my labia, slipping a finger inside, spreading my wetness all over my pussy. By this time I had made quite a puddle on the couch. I spread my legs as wide as I could, and circled my clit. I wasn’t going to be able to take much more of this before I came.

Jason handed me the blue dildo from my backpack. “Use this.” He said “She’ll like it.”

“Yeah.” Jill said “Use it.”

I closed my eyes and slid the big plastic toy up my pussy. The feeling of fullness was incredible. Slowly, wanting to enjoy every second, I started fucking myself with it. When I opened my eyes, Jill had unbuttoned her jeans, and had a hand down the front of her panties. But her eyes weren’t just fixed on me anymore. Jason had taken off his pants, and was stroking his big cock as he watched me fuck myself. I smiled. So Jill was getting a double eyeful tonight.

I felt my orgasm coming, and suddenly that was the only thing that mattered. I started fucking myself furiously hard, enjoying the feeling of the base of the dildo slamming into my clit as I pulled on my nipples. I knew I was making noise, but I wasn’t really conscious of it. I just needed to come. Then I felt a finger between my ass cheeks, tickling my anus. I realized that it was Jill’s long finger invading me there. As she penetrated my asshole, I came, thrashing and moaning. It kept going, wave after wave, as Jill’s finger penetrated deeper and deeper inside my ass. I closed my eyes and let the orgasm wash over me. Finally it was done, and I could breathe again.

I let the dildo slip out of my gasping pussy, and opened my eyes. Jill had her pants down, her hairy bush on display. She had a beautiful triangle of curly dark hair covering her mound. She had taken her sweatshirt off, and her smaller tits were jiggling as she moved. One hand was busy between her thighs. The other hand was occupied with Jason.

Jason, still wearing his t-shirt, was sitting next to me on the couch. Jill’s hand was wrapped around his rigid cock, pumping him for all she was worth. Her hand was moving so fast it was almost a blur. He was swollen; his cock head was bright purple and leaking clear precome. I knew he was about to come. Jill’s breasts were shaking in time with her hand. Suddenly Jason shouted “Fuck!” His back arched, his ass raised up off the couch, and jet after jet of pearly white come shot out of his cock, splashing all over his stomach and chest. Jill milked every drop from his wilting penis. There was a lot of come. I dipped my finger into one of the large pools of come on his stomach, and licked his salty essence off. He’s a vegetarian, and I’ve always liked the taste of his come.

“Wow.” Jill said, still fingering herself. “That was a lot.”

It was too much for me. I had to lick her pussy, I had to taste her. I came at her from behind, burying myself in her soaking wet folds, licking and sucking and drinking her. I was overwhelmed with her scent; the intoxicating mixture of sweat, sex, ass and pee that was now all over my face. As I slurped, her fingers were busy with her clit. She was surprisingly rough with her little button, grinding it with two fingers. Then she rolled over, kicking off her bunched up jeans and panties and spreading her legs wide, giving me full access to her pussy and clit. Her labia were purple and swollen and glistening with wetness; her clit was bright pink and swollen. I attacked her sex with a vengeance. I slurped her swollen clit with my tongue while I fingered her pussy and her little asshole. Jason watched us, playing idly with his still soft cock, as his little sister’s friend squealed and wiggled as she came on my face. She squeezed me tightly between her thighs, pulling my hair, pulling me into her. I couldn’t breath. I was covered in her wetness. When at last she was still again, we kissed for a long time.

We all got dressed and finished our beers. I went home, Jason went to his bed, and Jill to an air mattress on the floor. I don’t know if anything else happened that night, but I am certainly looking forward to our next scrabble night.