First Time Threesome

Years ago, before I was married, I was dating a girl named Wendy. Our sex life was great, and one night, I found a copy of Penthouse Letters tucked under her bed. Pages were folded over to mark a number of different stories, and they all involved three-ways with another guy.

I asked her if this was her biggest fantasy, and she said. "Sure, wouldn't you like to be with two women?"

I then asked if it was only a fantasy, or did she want to make it a reality. She said she might be willing to try it, and I told her I would make it happen, if she would, later on, invite another woman into our bed. She agreed, and we started talking about who the guy might be. She said she would be more comfortable with one of my friends, as opposed to a total stranger, and I had two friends who she found hot.

One of them was my closest friend, almost like a brother to me, so I knew I could trust him not to talk. She agreed, and I said I would approach him.

I called Bob up, and we both went out for a beer and bite to eat. Part way through the meal, I nervously told him of our plans, and asked if he would be interested. He seemed shocked at first, and seemed surprised that I would want him to fuck my girlfriend, but said he thought she was hot, and readily agreed.

When I let Wendy know that Bob had said yes, she became a little nervous at the thought of him actually fucking her, but excited and turned on at the same time. We set it up for the following Saturday. Wendy wanted me to invite him over for supper, and then said we would later go out dancing, before coming back home to play.

Bob showed up on the planned night, and we had a great dinner and normal conversation. Of the three of us, he was, by far, the most nervous. Wendy was wearing jeans, and a top with no bra. She has big nipples, like pencil erasers, and they were jutting out, the whole meal. I could see Bob stealing glances.

After dinner, Bob and I watched hockey on TV, while Wendy got ready to go dancing. She came out of her bedroom, in a body-hugging mini-dress, and looked sexy in her 4" stilettos.

We then hopped into my car, and drove to the nightclub. We met some other friends there, and enjoyed lots of laughter, and a few drinks. Wendy took turns dancing with both of us, while flirting nervously with Bob.

About 11:30, we decided to call it a night, and go back to our place. Once we arrived, no one seemed to know how to get the ball rolling, so I took the initiative. I told Bob, that to get ready, he should take a shower, and wash off the sweat from dancing.

Meanwhile, Wendy had dozed off on the couch, probably wondering if anything was ever going to happen. Once I found Bob a towel, I then sent him off to the shower. I gently shook Wendy awake, and told her to go join Bob , so that the two of them could have some alone time to get comfortable with one another. This way, they could start things off, without being having to be nervous about me watching them fuck.

She looked at me with her eyes bugged out, and said "Oh God, I can't do this."

I told her that if she didn't want to go through with it, I would understand. The night before, she admitted to being nervous, and said that though she thought she could fuck him, she wouldn't give him a blowjob, because that was getting much too personal, and it was reserved only for me. I told her that if she couldn't let go completely, and enjoy herself, then maybe we shouldn't even consider it.

Now here we were, at the crucial decision time. Wendy stared at me, not saying anything for about 15 seconds, and then quickly got up and walked nervously, to her bedroom.

I followed, and watched, as she stripped down to her undergarments, a matching bra, garter and stockings. Leaving them on, she walked, tentatively, to the bathroom, with me trailing behind, reached for the doorknob, and took a big nervous breath before opening the door, and walking in.

Like a pervert, I stood at the door listening. I heard her ask: "Mind if I join you?", then silence, as I imagined her doing a sensual striptease for him.

I heard her join him in the shower, then some nervous conversation, Bob nervously asking her all about her brother, then more silence, then heavy breathing and panting. God!!, I was so turned on, I thought my cock was going to poke a hole through my pants.

I reluctantly walked back to the living room, to give them privacy, and stripped down to my shorts. I then sat on the couch, and tried to watch TV, with very little success.

This is what happened in the shower, which I of course found out later from the two of them:

They stood under the water, soaping one another up, when Wendy lathered up her hands, and reached for Bob's, already hard, cock, and sensuously started stroking him. They locked lips, and started kissing. Bob then pulled back, bent down and took a nipple in his mouth, while also reaching for her pussy. At first he started to play with her clit, then slipped two fingers inside of her, and started sliding them in and out. Within a few minutes, Wendy's legs started getting weak, as she approached her first orgasm of the night. Bob spun her around, bent her over, with her hands against the shower wall, and plunged his cock deep inside of her from behind.

At this point, I could hear the slapping of flesh, all the way from the living room, as he drove in and out of her, bringing her to yet another orgasm.

After a number of minutes, Bob was ready to explode, and not knowing whether it was okay to come inside of her, he pulled out and shot his cum all over her ass and back. They stood under the shower, caressing and cleaning one another, rinsing the cum off her back, and then, climbing out of the shower, towel dried one another off.

I was sitting on the couch, with an erection like a steel rod, when Wendy came out of the bathroom, flushed, naked, nipples fully erect, leading Bob, her new boy toy, by the hand. He trailed behind her, already fully erect, his cock bobbing as he walked.

The two of them walked right by me, on the couch, on the way to the bedroom, and I'm not even sure if they knew I was there. If they did, they didn't care or give any indication. I wanted to jump up and join them, but decided to give them a few more minutes of alone time.

Very shortly, I heard an unmistakable and very familiar sound. Somebody was getting a blowjob, and it wasn't me. It sounded like Wendy's rules had gone right out the window. Good for her. This I had to see, so I got off the couch, and made my way to the bedroom.

It was a sexy scene, as Wendy had lit a number of candles, and was on her knees, ass in the air, rewarding Bob with her finest effort at the ultimate blowjob. I watched, as his cock slid in and out of her moist lips, her hands busy working his shaft. I watched her put his whole cock in her mouth, until her nose touched his pubic hair. Bob had his head thrown back, obviously enjoying the effort. I certainly know that I was incredibly turned on.

After ten minutes or so, of Wendy slurping, sucking and licking, Bob reached down, and pulled her up until they were locking lips, with her lying on top of him, with his cock between her legs, caressing her wet slit. After kissing for a while, he spun her around, so she was now on the bottom, put his hands on her thighs, and spread her legs wide open. He then drove his hard cock, all the way inside of her, with the first thrust. He started humping her with abandon, and I could hear Wendy's familiar humming and moaning start to build to an orgasm.

I watched, in fascination, as her cunt lips gripped his shaft, while he slid in and out. After another 5 minutes of fucking, Bob pulled out, and sliding his body down, he put one hand on each thigh, and pushed her legs as wide as they would go. He then lowered his mouth to her pussy and started to lick her slit, flicking her clit, with his tongue, and plunging it deep inside of her. She grabbed his head and shuddered.

Fascinated, I moved up, and sat on the edge of the bed, near Wendy's head. Her eyes were practically rolling back in her head. She looked up at me, and whispered, "Thank you", while reaching out and pulling my penis out of my shorts. She eagerly stuffed it into her waiting mouth, and started bobbing up and down, while Bob continued to eat her out.

After a few more minutes of this, I stood up, removed my underwear, and ordered Wendy to get on her hands and knees. I crawled onto the bed, and kneeling, shoved my cock back down her throat, as Bob mounted her doggy style, his hands squeezing her ass. Here I am, facing my best friend, fucking Wendy's mouth, as he fucks her pussy, and we both grin at one another. We were close enough to high-five. This seems surreal to me, and I know I'm way too excited to last very long. I hold the back of her head as I keep plunging into her warm, wet mouth, wanting to cum.

Bob, meanwhile, has pulled out, and lying on his back, slides underneath her and starts to suck on her pussy. I explode into her mouth, and can feel her swallowing my seed, as she pumps me dry. I pull out, and move aside to let Bob have his turn to cum.

Wendy pulls him up to the headboard, and with him lying on his back, lowers herself onto his cock, and starts to ride him with abandon. I know her well, and can tell when she has just one goal in mind, and that is now her own orgasm. At this point, Bob is just along for the ride, but I certainly don't see him complaining, as Wendy starts bouncing even harder and faster. She is so lost, in her ecstasy, that she isn't even aware that she's bouncing the top of his head off the headboard. She orgasms with her usual "Oh Fuck, Oh Fuck", as Bob explodes inside her.

Spent, they lay there, quietly kissing, as they both come down from their highs. She rolls off of him, and lays on her back between us, looking over at me with a huge grin. Everyone lays quietly with their private thoughts for a while, then Wendy gets out of bed, to go and use the bathroom. As she walks away, Bob watches her and then turns to me and says "Man, she's got a really great ass", as a big shit-eating grin spreads across his face.

When Wendy returns, she's now re-energized, and ready for another round. She climbs back into bed between us, and starts stroking Bob, as she climbs on top of him. She tries to insert him, but he looks at her and says "Sorry Wendy, I'm not hard enough yet."

"Oh, that's OK", she says, and without missing a beat, she lowers her mouth to his cock, and starts sucking, badly wanting his hard cock again.

Bob looks over, and seeing that I'm already hard, says "Why don't you climb on Kevin first?"

Without missing a beat, Wendy straddles me, and inserts my cock. She rides me with reckless abandon, until both of us have another orgasm, and rolls off of me, onto her back.

Watching the action, Bob is finally hard, once again, and climbs on top of Wendy, ramming his prick into her cunt. She places one hand behind his neck, and the other on his ass, heels hooked on the back of his legs, as she urges him on.

Pretty soon I recognize her "I must cum" face, as she grabs his ass with both hands, both of her feet waving in the air, as she pulls him in deep, urging him to go faster. "Oh fuck, oh fuck, oh fuck" she says, exploding into yet another orgasm. Within seconds, I see Bob's ass cheeks contracting, as he dumps another load inside of her.

They lay there softly kissing for a while, as Bob goes limp and slides out of her pussy. Shortly after, he gently climbs off of her and goes to use the bathroom.

While he is gone, she gives me a kiss and says "Thank you, I think I owe you. Can we please do this again, real soon?" Spent, we all fall asleep, Wendy between Bob and I.

In the morning, I wake up, spooning Wendy from behind, and remembering the night before, I am almost immediately hard. I reach around, and cupping a breast, start tweaking her nipples. I reach down, between her legs, and find her pussy soaking wet already. With no foreplay, I slide in from behind, and start pumping.

While I'm busy fucking, Bob is still asleep, on his side, facing Wendy. She reaches down and grabs his cock, and starts stroking him. He wakes up, and they start kissing, as he plays with her breasts. Feeling horny now, Bob reaches for her pussy, not knowing yet, that I'm already in there. Her cunt milks me dry once again, then she rolls onto her back, spreads her legs, and reaches her arms out, inviting Bob to fuck her, as she pulls him inside of her.

He doesn't hesitate, and starts humping at a slower pace than before. This time, he lasts quite a while, and Wendy, with her hands on his ass, is pulling him in deep, as she builds to another big "Oh fuck" orgasm. When he is done, he hops off the bed to go use the bathroom, and Wendy turns to me and says "That was the strongest orgasm I've ever had in my life."

Bob and I played on the same hockey team, and that morning, we had a game to go to, so we both showered, had a quick breakfast, gave Wendy a goodbye kiss, and then hopped into my car.

As we pulled away from the house, Bob looked at me and said: "I can't believe we just did that. Holy shit!"

Wendy later told me, that she thought her heart was going to beat right out of her chest, and that her orgasms were all, by far, the most intense that she has ever had.

It was not the last time we got together with Bob, and yes, I got my three-way with two females, but that's yet another story to write.