Here is one of my favorite masturbation fantasies in which I have anal intercourse with a man for the first time. It starts with my wife Pam and I finding another couple on a swingers website. We arrange a meeting with Steve and Sally at a motel. The first time we get together, we decide to just get to know each other and watch each other fuck. We meet at the motel and go out for lunch. When we come back, we all strip. Pam and I fuck as Steve and Sally watch us, and then Steve and Sally fuck as Pam and I watch them. We all enjoyed the experience. Watching a live sex show was so much fun, and performing in one in front of an audience was even better. Next time we agreed we'd swap partners.
For our second meeting, we do the same thing with partners swapped. Sally and I watch Steve fuck Pam. Pam cums three or four times as she always does. It's not just me. Sally and I have our hands all over each other as we watch the Steve and Pam show. When it's our turn we're really hot and ready. Sally and I are really good together. We put on a good show for Steve and Pam. We all enjoyed performing for each other, even more this time. We plan anal sex fun for next time.
Our third meeting is just for anal sex. I fuck Sally's ass as Pam and Steve watch, and then Sally and I watch Steve give Pam a really hard ass fucking. Getting fucked in the ass makes Pam cum multiple times. Sally likes it a lot too.
The fourth time we get together, things start going in a bi direction. After we all strip, Pam and Sally embrace, and kiss and hug as they roll around on the bed together. Then they make each other cum over and over with hands, lips, dildos, vibrators, and other toys. After an hour of this, they seem satisfied. Steve and I enjoy the show immensely, as our hard cocks attest. I can't help playing with mine and have to catch myself before I masturbate.
Pam and Sally both insist now it's their turn to watch Steve and I make each other cum."You don't have to hug and kiss. We just want to see hand jobs and big squirts of cum," Sally says. Steve and I refuse to touch each other at first. After lots of persuasion, Sally gets gets Steve to let me grab his cock, but Steve goes limp. Pam comes over to help. She cups Steve's balls and fingers his ass. Finally Steve starts to stiffen in my grip, and I start pumping. Steve takes a long time to cum. I have to pump hard and change hands several times. I use my other hand to caress the sides of Steve's butt. Finally after 20 minutes Steve has an orgasm with an impressive load. Pam and Sally applaud.
Now it's Steve's turn to give me a hand job in front of Pam and Sally. I have Pam and Sally sit on the edge of the bed. I stand two feet in front of them. I have Steve stand behind me. I reach back with both hands and guide Steve's left arm through my parted legs and place his left hand on my balls. He cups me just right with a huge left hand and I close my legs over his left forearm. I reach back and pull his right hand around my waist and place it on my cock. He squeezes me and I'm instantly hard. Then I clasp my hands behind my head and lean back against Steve. Steve starts to pump me, and Pam and Sally with their close up view get excited. Pam and Sally giggle and talk about how close I am to cumming and how far I'll shoot. "He's close now," Pam says as I'm shuddering a little and moaning louder. Then Steve gets into it. He suddenly cups my balls harder with his left hand, and squeezes my whole pelvis with a forceful bending of his left elbow. The powerful crotch hug lifts me up onto my tip toes and pulls my torso back hard into his. As he does this he starts pumping my cock furiously with his right hand. I can't hold off if my life depended on it. With a series of grunts and a whole body spasm, I fire my load, hitting both Pam and Sally. They laugh and applaud, both for me and Steve.
On the fifth time we meet, Pam and Sally stay dressed and they order Steve and me to strip. "We're just going to watch and play with you guys tonight," Sally says. Pam and Sally have obviously discussed this in advance. They both know that Steve and I are both anal erotic because they order us to the bathroom to give us several large enemas, which all four of us really enjoy. Then they lay us down on our backs on the bed side by side over beach towels with out heads at opposite ends of the bed. Sally spreads my legs wide, lubes my anus, and penetrates me with a life-sized dildo as she starts working her well lubed hand up and down my hard cock. Pam does the same thing for Steve. Steve and I moan together in ecstasy. We are both close to the brink when Pam and Sally suddenly stop and back off.
"Foreplay is over, and now it's time for the hubbies to put on a show for the wives and fuck each other," Sally announces. Pam laughs. "Tonight we girls get to watch you two hunks fuck each other in the ass." I'm excited, but Steve loudly protests. "I never have, and I never will," he says. Pam and Sally try to persuade us. Sally says, "You guys obviously like things up your asses, so what difference does it make if it's a dido or a another guy's penis?" Steve still refuses to go along. "How about you, Bill?" Sally asks. Pam answers for me. "I bet he wants it. He loves me to peg him." Then Sally threatens Steve. "If you don't let us watch Bill and you fuck each other, then you can play with yourself for six weeks while Pam, Bill, and I have hot threesomes. I'm serious!" Steve and I look at each other. Steve has a worried look. I smile at him and shrug. "OK, you win," Steve says. Everyone but Steve excitedly laughs.
We flip a coin to see who goes first. If it's heads, Steve Fucks me. If it's tails, I fuck Steve. It's tails. I decide to fuck Steve's ass the same way I like to fuck Pam's ass. I make Steve kneel on the bed with his knees spread, and get down on his elbows with his hands supporting his head. Steve's wide open ass sticks up invitingly above the rest of his body. I crawl up on my knees right behind Steve. I'm surprised how much I like the feeling of my thighs on his. I lean back a little to lube Steve's entire butt, his taint, and the back of this thighs. Then I use one, two, then three fingers to lube his anus and deep inside his rectum. Finally, I lube the front of my thighs, my pubes, and I generously lube my hard cock. I push myself tightly up against Steve so my erect cock rests along the length of Steve's butt crack, and I move my hips around and around to make sure every point of contact between Steve and me will be well lubed. Pam and Sally squeal in excited anticipation. I move my cock down underneath Steve's crotch and squirm around again pressing and moving my bare pubes all over Steve's butt. We are lubed and ready to go.
Pam and Sally excitedly cheer, "Fuck him! Fuck him! ..." I lean back a little and position the head of my hard cock right over Steve's anus. I move it around playfully with slight pressure so that Steve's anus opens very slightly. "Fuck him! Fuck him! ...", Sally and Pam chant louder. I push a little harder and the head of my cock pop's through. I just hold it there. Steve really wants all of me inside him now. He pushes back against me, but I've got his hips in my hands and I don't let him. He squeezes me hard with his internal muscles and tries to suck me into himself. "Fuck him! Fuck him! ..." Then I very slowly push myself half way into Steve and hold it there. Steve and I both moan. It feels really good. "Go! Go! Go! ...", Pam and Sally yell. I wait another few seconds enjoying Steve's contractions. Then Sally sneaks behind me and gives my butt a hard pop with the palm of her hand. That makes me jump and I bury my cock inside Steve. After the first full thrust I go crazy fucking Steve. I can't help going in and out very rapidly. Steve is moving too in perfect time in the opposite direction. Steve's butt and my bare pubes smack into each with loud pops at a furious pace. Pam and Sally cheer loudly. After a few minutes I suddenly hit the point of no return and I can't help pumping faster and faster at a rate of four or five pops per second until I cum hard and collapse on top of Steve. Then I roll off of him to one side and fall into a blissful stupor on the bed.
"Wake up, Bill. It's time for Steve to fuck your ass now," Sally whispers in my ear as she strokes my butt. I feel Steve's knees next to me. He grabs me under my hips with powerful hands and pulls me up on my knees. Pam and Sally start to cheer again, "Fuck him, Fuck him, ..."