The Third Date
The next week end, I went to see my folks in the next state over, a five hour drive. I needed a break from the sexaholic woman, Jill, who’d worn me out over the period of only two weekends. While there, I got a long email from her, asking for her understanding in the following matter. She wrote that she was obsessed with having a threesome with me and another man. And that she’d contacted an old boyfriend who was up for the action. But he had conditions. First, he wanted to fuck her, and that he wanted pictures taken of the sex act and sent to me. Now, I’d only known her for a few weeks; I couldn’t say I was in love with her, as I wasn’t. The sex was great, but I had doubts as to this relationship ever blossoming. I truly think she was addicted to sex. It seemed to be always on her mind.
I wrote back that I would be good with it, if that was what she truly wanted to do. And I was okay with it, oddly. I suspected her ole boyfriend wanted to make sure I wouldn’t be jealous. She emailed me back with a dozen pics of this guy fucking her in various positions, and of her giving him a blow job. Actually it was kind of hot. It made me hard. I wrote back to set up the threesome for the next weekend.
I’d never had another man see my erection, and I was nervous about doing this and being able to perform in front of another guy. And another troubling thought seeped into my consciousness. Maybe she wanted to get back with this guy, and was just using me for her own sexual needs. Whatever, it was too late now, I’d let the chips fall where they may. When the two of them arrived at my apartment, he seemed a nice enough guy. Tim was his name. It was Saturday night, and I dimmed the lights in the apartment. We each had a few beers to loosen up.
To get the ball rolling, Jill performed a strip tease, a kind of a lap dance as she slowly stripped her clothing off. She’d donned some sexy lingerie with a thong, and she luxuriated in showing us her ass. Finally naked, she drew both us down on the carpet. She made both of us undo our pants and pull our cocks out. She took us one at a time into her mouth and made us hard. Once that was achieved and my initial embarrassment over, she playfully jacked us both off at the same time. “Two cocks, twice the fun,” she joked. “Tim, I want you to fuck my pussy while I suck Ted off. Then you two can switch ends.” She giggled.
She got on her hands and knees and spread her legs. She took my cock and put it in her mouth and began to suck me off. Tim positioned himself behind her and stuck his cock in her pussy and began humping her. She reached under herself and tickled her crack, rubbing her clit. She released my cock for a second to say, “Thank you guys. This is a dream come true. Thank you both soooo much.” For the next ten minutes, we worked her holes, and she worked our cocks. Tim was slamming her hard from behind, and periodically slapped her cute ass. Tim withdrew and jacked himself a few times and shot his wad onto her ass crack. Tim stood with his flagging cock and sat on the couch watching Jill suck my cock. Actually, it was quite erotic, having another man watch my stiff cock being serviced by Jill’s mouth. She let my cock out of her mouth, and said, “Cum in my mouth.” I jacked my cock twice and spurt my cum into her open mouth. She could have just let me come in her mouth as she sucked me off, but she apparently wanted either to watch me come, or for Tim to see me cum. Maybe both. It was shaping up to be an interesting night.
We sat on the couch and relaxed, all three of us buck naked, Jill sitting between us. We drank another beer and talked, joking some about our sex act. A half hour later, Jill began playing with our cocks, making us hard again. “Okay guys, round two. This time, Ted, you got my pussy, and Tim, I’m sucking you off.” Jill assumed the position, and began sucking Tim’s cock. I mounted her from behind, ramming my hard-on deep into her love hole. She moaned in pleasure. We fucked her for about ten minutes. Jill released Tim’s cock and told me to stop fucking her. I withdrew. Jill stood up. “Ted, stick your cock back in my pussy. Tim, lube your cock up with the Vaseline, and fuck my anus.” All three of us standing, we did as she directed. I entered Jill’s wet pussy and drove my cock all the way home. Tim was making progress up Jill’s ass, much to her discomfort. I could feel his cock on mine through the thin membrane separating us as he pushed it all the way in. We had her sandwiched. We began fucking her. Jill began to relax as her anus loosened up, and began moaning in pleasure. We continued in this fashion for about another ten minutes. I for one knew I wouldn’t orgasm so quickly after the first, and I was confident Tim wouldn’t either, though I kinda wanted him to so he would call it a night.
“Oh god, you two fucking me; feels soooo good. I’m gonna come.” She reached down and played with her clit. I felt a gush of her feminine emissions run down my balls as she came.
“I can feel her come,” Tim exclaimed. I could feel her pussy pulse on my cock also. It was erotic having a woman orgasm as I fucked her. She humped us madly now, our cocks sliding past each other in her hole.
A few minutes later, she exclaimed, “I’m gonna come again.” she moaned loudly. She worked her clit, sawing it furiously with her fingers and touching my hard cock in the process, feeling it slide in and out of her steaming pussy. “Ohhhhhh,” she wailed in ecstasy. She lost all control of her body as spasm after spasm wracked her. “Enough, please.” She pleaded. We withdrew from her abused holes.
We took turns in the bathroom cleaning up and resumed our positions on the couch, each of us guzzling another two beers down. I had a good buzz going, beyond being bashful in my nakedness in front of Tim. I was sure he felt the same way. After a fashion, Jill said, “It would be so sexy to watch you two do each other.” Whoa, this was an unexpected turn of events.
Tim asked, “What do we get in return?” I thought to myself, it had better be good.
“I’ll masturbate with my dildo while I watch you two take turns fucking each other in the ass. You can do it right here at my feet.” She dug into her purse and pulled out her battery powered dildo, and played the tip over her pussy opening. To my utter surprise, I was getting hard. Tim was also as he watched Jill masturbate.
I got on my knees and presented my ass to Tim. Now, to the reader of this story, I’m not gay, but I would only allow another man to put his cock in my ass while a woman watched. There must be a woman or women in play. That way the act is justified, in my mind. So anyway, Tim knelt behind me and lubed up his stiff cock. He put it to the pooper opening and shoved it in. It slid right past my sphincter and he rammed it home, and began fucking me in earnest. “God, that’s hot,” Jill moaned, her dildo sliding in and out of her engorged pussy lips. “Watching you to men have gay sex.” I was hard as a tree trunk. Tim picked up the pace, then withdrew and spurt his cum on my back and butt. I could feel his warm essence sliding off my skin. Jill moaned she was coming. “Watch me, I’m gonna come. Watching you fuck his ass and then spurt on his butt, Ohhhh shiiiiit!” She convulsed, spraying some of her cunt juice out. That was hot. Tim got up to retrieve a wet wash cloth and he wiped me clean of his jism.
I stood up in front of Jill as she continued to work her pussy, not content to have come only twice. “Tim, jack Ted off. Make him come on me.” Tim seemed happy not to have my cock up his ass, so he gladly wrapped his hand and fingers around my shaft and rub me. I bucked my hips. He put some lotion on my cock and resumed jacking me off. That’s hot, guys. Make him come,” she moaned. I wanted to spurt at the moment she had another orgasm, which shouldn’t be that far off. Jill teased me further to heighten my sexual excitement by saying, “Did you enjoy the pics of me and Tim fucking? Of Tim’s cock fucking my pussy? Of me giving him head? Did you? Tell me the truth.”
I moaned and nodded. “Yes, it made me hard, seeing someone else fucking you.” She came then a third time, and I spurt my cum out. It plopped onto her thighs and pussy.
“Oh god, that’s so fucking hot, watching you come.” Her spasms dying, she put her dildo down and relaxed. It was over. What an orgy. We cleaned up, got dressed, and said our good nights. Jill bid me a goodnight with a long French kiss. “I’ll see you tomorrow. I have something special planned.” Oh great. Jill just could not get enough sex.
I texted her after I’d showered and given her time to get home. I basically said I was concerned about her and Tim getting back together. I waited patiently for her to text me back. Instead, a half hour later, she called, waking me up. Apparently, I’d fallen asleep. It was Jill. “Hey,” I said in a way of greeting.
“You don’t have to worry about Tim. He’s engaged to be married next month. Besides, I don’t really like him. You, on the other hand, I do like. A lot. And it’s more than just sex and your luscious hard cock, Ted. Believe me. Okay?” I said okay, and that I enjoyed the night, and assured her again I wasn’t gay, that I did it to please her. “It’s okay to be gay, or have gay tendencies, Ted. I’d love you either way, strait, gay, or bi. But I really, really enjoyed watching you get fucked in your cute ass. That was smoking hot.” She giggled. “Save your strength for tomorrow, I got a big surprise. For you.” Oh great. What now?
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