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This story takes place about one month after Debbie, Cassidy and me attended our first swingers party.
My wife Debbie and our wife Cas are involved with Tony, aka Horse. They also have the occasional romp with a young man named Robert.
I call Robert their boy toy. He is 18 years old and just finished high school. He lost his virginity with my wife Debbie, and on the same evening he had his second pussy when he had sex with Cas.
I had a feeling about Robert, he made some contact with me after having sex with Cas. As he left the room his hand brushed up against my hard cock. He smiled as he passed also. I found myself admiring his ass as he walked away. My curiosity was piqued, but it did not happen again. That was until today.
It was a Saturday moning, the ladies had gone out to the mall for a day of shopping. I was home alone, which was actually a rare thing these days. I had set up a section of my basement as a work out area, and was currently down there all sweaty from exercising. I then heard my door bell ring.
Wondering who was at the door, I headed up the stairs leaving my shirt behind. I opened the door and there stood Robert.
He smiles while staring at my sweaty chest.
Robert is shorter than my 6 feet, he is about 5 feet 7 inches, the same as Cas. His weight was also less than me about 145 lbs. I am at 185 lbs. Robert has blond hair top and pubic. I have dark brown hair and black pubic hair. The biggest difference however is our age. He is 18 and I am 28.
Although he is 18, he does not look it. My ladies say they feel like they are robbing the cradle, when they have sex with him. The big attraction about him is his cock. He is 9 1/2 inches long (the ladies measured him).
I break his stare by saying, "Hey Robert what brings you over? The girls aren't here; they are out shopping."
He says, "I know, Debbie told me I should stop in to talk to you."
I say, "Okay, well step on in."
He enters, and I wonder what new thing Debbie and probably Cas have in mind with him, that they would have him stop in to talk to me, especially when they are not here.
He notices that I am a little sweaty and asks, "Working out?"
I say, "Yes, but its okay, I was just about done anyways."
He doesn't say anything and starts to act timid like the first day we met. That was when he got to have sex with my girls. After that he was very comfortable with the arrangement.
I ask, "So, what did you need to talk to me about?"
He hesitates, and then blurts out, "I think I am Bisexual. Actually I know I am. Debbie and Cas said I should talk to you."
So there it is, The girls set me up. They both know I am bi, and they want me to initiate Robert.
I say, "Have you done anything sexual with a man?"
He says, "No, I haven't, but I have watched videos, and I get aroused by them. I want to try it, and I want to try it with you."
He seems to blush a little. I know how he feels. My first time was intimidating also.
I ask, "So what would you say you would want to try?"
"Well I guess giving a blow job, and maybe taking it in my butt."
"So you are more of a bottom guy then? I myself am vers, which means versatile. I like it both ways in other words."
"That's what they said. So they told me I should come and see you."
"Okay, so now I know why you are here. So you know, I am interested. How would you like to proceed?"
"I don't know, I am a little nervous"
"I was too my first time. I was also the same age as you are now."
"Really?"
"No, shit. I tell you what, why don't you tell me how you have fantasized about doing it the first time."
"I guess I always start out thinking about giving the other guy a blow job."
"Okay, Why don't you sit down on the edge of the couch."
He does and I move up to him placing my now bulging shorts close to his face. I say, "Now take my cock out."
I was wearing elastic band shorts so all he had to do was lower them and my underwear.
He reaches for my shorts, and starts by feeling my bulge through the cloth. He then moves his hand to the front sides, slipping his fingers inside the band of my shorts and underwear. He pulls them away from me, and then down, releasing my cock which was fully hard. He looks at it while lowering my shorts and underwear far enough so they fell to the floor.
I stepped out of them and stood in front of him. He reached out and took hold of my cock and he starts to lightly stroke it. He was exploring, getting a feel of what another man feels like. He starts to move his mouth toward the head of my cock, he kissed the tip and then the sides of my gland. He slowy opens his mouth and takes the head into it. He withdrawls and does it again while he strokes me. This time he takes it in further, and slightly sucks on it.
Now he starts to bob up and down on my cock. He is giving another guy head for the first time. I make a mmmmm sound to encourage him. He looks up at me and I smile at him. He is doing fairly good for a first timer.
I let him suck me for a while, then I say I think we should take this to the bedroom.
He releases my cock, and gets up off the couch, and he starts that way. He had bicycle shorts on that hugged his ass. I have to say his ass was very feminine looking. I am primarily a bottom, but I think I am really going to enjoy taking his virgin ass.
He takes his shirt off and lies on the bed. I join him, and lay next to him. Not sure why but I went to kiss him. I am not so much into kissing men. It is more the sex that I want. Fortunately he wanted it. I reached down to his crotch and to his impressive cock. I felt it through his shorts. He was rock hard and huge. I slipped my hand under the edge of his shorts and underwear, taking hold of his manhood, causing him to moan.
I pull his cock out and stroke it. He is by far one of the biggest dick I have ever held. I break the kiss, and I move down his chest, suck his nipples a little, but my eye is on the prize. I move down further, and I take his pre-cum oozing manhood into my mouth.
He moans, and says, "Oh god." As I start to suck his cock. Another new experience for my young friend. His cock feels nice in my mouth. I take it in as far as I can. Debbie is the expert at deep throating, but I intend to train myself to do so as well. I sucked him for a little while, but I was sensing his impending orgasm, so I backed off.
I took him reluctantly out of my mouth, and moved between his legs and hiked his shorts and underwear off.
He says, "I'm clean back there, Debbie showed me how to do it."
I smile, thinking, that's my girl.
I ask him, "How do you do it in your fantasy? Are you facing the guy or bent over?"
He say's, "Doggie style, if that's okay?"
I say, "I am here to please you, so doggie style it is."
He rolls over and gets on all fours. I direct him on the proper position. Once he is there I have to say his backside is very inviting. He has almost a feminine quality to his ass, other than his nut sack hanging down. His little virgin pucker looks very inviting. Since I know he is clean, I decide to give him his first rim job.
He moans as I start to tongue his asshole. This is a first for me. I have done this to my wives, but never a guy. I was actually enjoying it. I pushed my tongue inside of him, making him moan louder. An incredible desire to fuck him came over me. I got up and retreived our handy container of lube from the dresser.
I get back behind him and start the ritual I am so familiar with. I am going to take my forth virgin ass. Three woman and now my first guy.
I place some lube on my finger then his anus. I rub around his opening and insert my finger. He makes a mmmmmm sound when I do. He is tight this is going to take some time. I remove my finger and add lube. I reinsert it and advance it enough to contact his prostate. I begin to rub it through his anal wall and that makes him moan and say, Mmmmmm that feels good.
I rub it with my finger and reach down and around and stoke his cock. I touch the head and he is oozing pre-cum from the stimulation to his prostate. I pull my finger out and apply more lube to two of my fingers and I insert both in his ass.
Robert moans loudly as I finger-fuck his virgin ass. He is relaxing more now. He still feels tight, but he is loosening up. I go back to rubbing his prostate which makes him moan and say, "Oh man, that feels so good!"
I decide to leave his cock alone as he may cum and I want to see if I can make him climax with my cock in his ass. I pull my fingers out again causing him to moan with disappointment. I apply more lube and attempt three fingers this time. I feel him stretch as I work them in. So far so good. This might be easy for him being so relaxed and wanting. He is living his fantasy as I did my first time.
I think the time is come for Robert to take my cock. I pull out my fingers and apply lube to my cock and get into position behind him. His ass looks so inviting, and it is making my cock twitch with desire.
I tell him, "Robert, I am going to try to put it in now. Are you ready for me?"
"Yes, I am. I'm ready."
I tell him, "Just relax yourself as much as possible, and I will do the rest."
I place the tip of my cock against his anus. He is breathing heavy and makes a mmmmm sound.
The tip is easily entering his opening. I am up to the edge of the head of my cock. I know once the rim of it enters him it will be the big stretch and may hurt. I want to just shove it in, but I want his first experience to be memorable in a good way.
I advance a little more making him moan. He pushes back, causing my cock to slip in more. He moans out an, "Oh Yes!"
My cock is in his ass past the spinkter. He felt tight. I did not move to let him adjust. I slide in a little more to Robert's moans.
He seems to be handling it so I pull back and slide back slowly.
Robert moans to that, he is ready. I pull back again and slip forward but dont stop. I start to fuck him to his oh's and ah's.
I have to say he feels goos and tight as I fuck him. looking down at his asshole wrapped around my cock, I would not be able to tell I am in a guys ass. I am also in my first male virgin ass.
He fucked him, holding his hips and rubbing his cheeks. I would spread them apart to get a good look. He moaned and told me how good it all felt.
I was starting to get close and I let him know. I asked, "Do you want me to cum inside?"
He Says, "Yes, I do, please!"
"Okay," I start to pump him a little faster and I feel my load built up and I say, I'm going to cum Robert!"
I orgasmed hard and I shot my load in his virgin ass.
When I finally squeezed out my last drop, I pulled out of him. I see my semen ooze out as I do.
He lays on his stomach and then his side. I lay next to him. I ask, "So did you enjoy that? Cause I did."
He said, "Yes I did, thank you, but that was the first part of my fantasy.
I say, "What's the second part?"
"I get to do that to you."
"Okay, give me one moment, and I'll be right back."
I head to my bathroom, I need to be clean for him. My cock is getting hard again thinking about his big cock in me. His cock is 9 1/2 inches long.
I did what I had to do and came out to Robert's smile, and the vision of him stroking his cock.
I smile and climb on the bed next to him. we kiss, and I take over the stroking of his cock. He is oozing a lot of pre-cum. I want to take him in my mouth, but that would make him cum. Hopefully he will last long inside of me.
He asks, "Can I fuck you now?"
I like his enthusiasm.
I say, "Yes you can. How would like me to be?"
"Turn around for me."
"Okay."
I get into the position he requested on all fours presenting my ass to him.
He picks up the lube, opening it. He applies some to my asshole and inserts a finger.
Mmmmmm, My body acts naturally to this intrusion. It craves more and will soon receive it.
I actually taught Robert how to lube an ass. The day he took part in Debbie's gangbang I had showed how to using her butthole. He fucked her in the ass right after.
He had now moved to two fingers in my ass, and he also found my prostate and was applying pressure to it like I did to him. I moaned to let him know I liked what he was doing. Damn, it felt good.
He asks, "Are you ready for me Daniel?"
"Yes, I am Robert."
He removed his fingers and applied more lube to my ass and then his cock. My ass has been well fucked so he doesn't have to take it slow. He places his cock against my anus and slips it in. It felt fucking wonderful. He started to fuck me. Slowly then picking up the pace. I moaned and said, "That feels so good Robert, your a pro at this."
That's when I heard the girls come in. Debbie and Cassidy came home early. They stood in the doorway and watched
their husband taking it in the ass. Neither of us flinched by there appearance. Robert continued to fuck me and I continued to moan with pleasure.
Soon he started to grunt and said, "I'm cumming!"
I felt him fill my ass with his cum. Technically he has now fucked the three of us in the butt. Not bad for Robert.
When he finally withdrew from me, he laid down next to me as I turned over. The girls where stripping and joined us in the bed. Cassidy said, "That was hot."
Debbie said, "Yes it was, can we join in now?"
We had a nice little orgy afterward.
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