First a little about myself. I'm a married white male and just turned 50. My sex life is very blah and damn near non-existant. I am on the reserved side and find it difficult to talk to strangers and meet people. Lately I have been thing about having some fun and excitement outside of the house. One of my biggest fantasies is having a woman use a strap-on on me.
Me laying on my back with my legs up so that way I can see the woman approach me and start using it on me. I've also been fantasizing about playing with another man. Wondering if I could feel a differnce between a dildo or a real cock in my ass. Plus I'm curious about sucking on a cock and seeing what the pre-cum and cum tastes like. So I started browsing on craigslist.
I'm looking for someone around my age and they can host. I'm looking in both the men's and woman's categories. I finally started talking to a man, John, and ended up meeting him at Walmart. We were talking and even though he is married also, he can host. But his wife does know about his fooling around with men and I have to meet his wife Mary to get her approval also.
Talking about strange and exciting. I'm thinking to myself, "Is she going to be home when John and I are fooling around? Is she going to be watching? Is she going to join in?". I didn't want to ask John none of this because if Mary approves of me, I'll be finding out sooner or later.
The next week I meet up with John and Mary so I could get Mary's approval. She was hot. I'm thinking, "The hell with John, I want Mary!". Well things went good and I got Mary's approval for John and I to play. Now I'm really getting excited and nervous. First, I've never been with a man before and thinking about if Mary was going to be there with John and I just made it that more exciting and much more nervous.
We scheduled our first get together for the following Friday. For the rest of the week I was in turmoil. I was excited, constantly fighting off an erection thinking about it, and not knowing if Mary was going to be there added to the excitement. But all of this also made me nervous as hell and was actually thinking about calling it off. Now I did tell John that because I'm only curious about this that I'm not sure how far I could go.
I told him we will definitely have to watch some porn so I could get worked up. Hopefully I would at least give him a hand job on our first get together. He understood and said we will go at whatever pace I am comfortable with. Well Friday came around and I'm like, "The hell with it". I going to do it. I get over to his house Friday evening and as we proceed to his basement, I'm looking around to see if I see Mary anywhere.
She's nowhere to be seen. I am happy about this because my stomache is in knots and I don't need the extra anxiaty right now. Still a turn on fantasing about her watching or better yet joining in but I need to do baby steps.
Took everything I had to show up. I hate being reserved and shy. We got to the basement, John convinced me to to go ahead and strip down. I nervously stripped down. John was also stripping down. I was so damn nervous, my cock wasn't only limp as hell, but I think it was trying to hide. Talking about being embarrassed. I sat on the couch, and John went over and loaded up a DVD.
No soon as he sits down on the couch, I hear Mary hollering at John, "What the fuck is this? You know you can't play with the new toy before I do." "New toy?" I thought to myself. What the fuck is she talking about. What the hell is she doing here?
I want baby steps damn it. John started to say something and Mary told him to shut up. She hollers "Come here, both of you". John and I get off the couch and start walking toward her. I want to run as fast as I can and get the fuck out of this situation but she is blocking the stairs and my clothes are behind me in front of the couch. To make it all worse, I'm approaching this hot woman and my cock is so tiny right now it is embarrasing as hell.
I'm waiting for her to start laughing her head off while pointing it. Now, let's get something straight here. I am a little bit above average from what I've read about the average penis size.
I'm about 6.5 " length and just under 2" girth. We get over to Mary and she puts her hand on my shoulder and presses down while telling me "Down on your knees". John moves in front of me and Mary says "Suck my husbands dick". I hesitate and she screams at me "NOW!". I lean forward towards John's cock. He is only semi-erect at this time and I see that he is already oozing pre-cum. Now he looks like he is pretty well endowed.
Looks like he is bigger than I am but I wouldn't say he has a monster cock. I open my mouth and wrap my lips around his cock head.
I can taste his pre-cum. Not too bad really. With my tongue I swirl his pre-cum all around his cock head. Well, I guess I was taking too long. Mary screams at me, "Don't just fucking play with the head. Take that cock all the way in." She puts her hand on the back of my head and starts shoving it forward.
I can feel John's cock growing larger in my mouth while it's going in deeper. The head of his cock starts hitting the back of my throat, I start gagging a little, and I start pulling back. Mary screams "I said all the way in" and forcefully shoves my head forward. John's cock is all the way into the back of my throat and I am starting to gag big time.
Mary is laughing and John hollers "Oh fuck". I don't know if it was the feeling of me gagging on his cock or what, but I think he was about ready to cum. Mary grabbed my hair and pulled me off John. She looked at John and said "Not yet". I think she meant that he couldn't cum yet.
Of course during all this, my cock is coming alive. I'm now oozing pre-cum also. Even though I'm scared shitless on what is going on, I think it has to do with my other fantasy about a woman dominating me with a strap-on. Mary looks at both of us and says "Stay. I'll be right back". She heads up the stairs and I look at John.
He just shrugs his shoulders with an expression on his face saying "I don't know". I hear Mary coming down the steps. I look over and here she is coming down the steps almost totally nude. She is wearing a strap-on! Could it be possible that both of my fantasies are coming true at the same time?
The dildo she was wearing wasn't very big.
Probably 6" in length and 1.5" in girth. Still making me nervous though about having anything shoved in my virgin ass.
And I'm assuming she is planning on doing that to me. Deep down I hope she does. She tells John that she is going to fuck the new toy first. "So I'm the toy she was talking about earlier" I thought to myself. She makes John and me get into a 69 with John on his back and me on top with my ass sticking up in the air. She makes us start sucking each others cocks again. We are both currently limp at this point.
I lower my head down to his cock and grab his balls at the same time and manage to put his cock and both balls into my mouth.
I start swirling my tongue around everything and can feel his cock growing in my mouth. In the meantime, he was slowly sucking on my cock get it hard, gently tugging on my balls with his hands, and spreading oil all over my ass. He then sticks a finger into my ass and starts finger fucking me while sucking on my now extremely hard cock.
Damn it felt good. But then I felt what felt like a cock pressing against my ass. I'm totally confused. My cock is in his mouth and his cock is in my mouth. I forgot all about his wife with her strap-on. Before I know it she has shoved the head of her cock into my virgin ass. Poor John, I damn near bit his cock in two. I heard a little yelp from him and his wife started laughing. I regained my composer and was waiting for what was coming next.
She pulled her cock head out of my ass (I wasn't expecting that) but then thrusted it back in going in just a little bit deeper. She backed off just a tiny bit and then thrusted back in just a little bit further. It was she was pulling it back out half an inch and then thrusting an inch back into me. Damn it hurt. Damn it felt good. It seemed like the deeper she went the more she was stretching my ass apart. I guess her cock girth kept getting bigger all the way back to the base of her cock.
She is thrusting her cock into me at a regular pace so I got the timing down so I wouldn't bite down on the hard cock that is in my mouth. I got to remember that he can just as easily bite down on mine in reaction to me biting down on his. I believe his wife knew this and was getting a kick out of it. Like I said earlier, it was just an average size strap-on. 6" long and 1.5" girth (at least in the center, felt like 15" at the base). But damn, that was the longest 6" I've ever felt.
I thought her thusting her cock deeper and deeper into my ass was never going to end. I finally felt her hips pushing against my checks. Thank god. I don't know if I could have taking any more. She just stayed there like that for a few seconds then slowly started pulling her cock out. It felt like she was about halfway out and then wham. She shoved that fucker all the way in at once. I think she actually got 7" of the 6" into me LOL. And she still kept pushing harder into me and rotating her hips while doing it.
Now she started reversing the process. She would pull out a bit and only thrust it back in half the distance that she pulled out. She did this until just the head of her cock was in my ass.
Then she pulled the head out and shoved just the head back in. She kept doing this for I don't know how many times. Then she shoved it all in in one move. Damn I was in ectasy. Feeling her cock filling up my ass all at once like that was bliss. I guess she knew what she was doing earlier about getting my ass ready for a good fucking.
She just started pounding my ass with her cock. John is still sucking my cock during all this. I wasn't doing a very good job at sucking his. My attention was on the cock in my ass. I don't know how I haven't exploded by now, but it was coming very quickly.
She could tell I was about ready to explode all over John's face and in his mouth when she suddenly pulled all the way out of me and knocked me off of him. I started reaching for my cock to finish off and she yelled at me that I better not even think about it.
Damn, my balls were so swollen with the build up they actually ached. I didn't know what to do. She helped me up (my legs were a little wobbly) and led me over the the coffee table in front of the couch. She had me lay down on my back and pulled my arms above my head. They had some kind of restraining system on this table because before I knew it she had my hands tied. She then told John that it now his turn to fuck me.
This coffee table is the kind that the top lifts up to make like a big tv tray out of it. It brought me up to just the right height where my ass was at waist heigth. Now her husband is fairly endowed. He's about 7" and probably about 2" girth. John grabs my legs and pulls them up and toward my head so my ass is up in the air and exposed to him. He presses his cock up against my ass and slowly pushes his cock into me at a steady pace.
Fuck, I can feel the heat from his cock in my ass. Totally different from his wife's strap-on. I start squeezing my ass muscles around his cock and I swear I could actually feel his cock throbbing in me. He steadily keeps entering me until I feel his balls pressing up against my ass checks. Even though he's a little larger than the dildo that Mary used on me, it felt damn good.
I got a feeling that they have done this before and they know just how to break in a virgin ass. He fucks my ass at a nice and steady pace at first but as he's getting closer to cumming he picks up the pace.
He starts ramming his cock deep into my ass until he finally explodes inside of me. I can feel his hot cum inside my ass and it feels great. It gives the ass fucking a whole different feel using cum as a lube instead of regular lube. I can feel his cock slowly softening up inside of me and I am squeezing it as hard as I can trying to get every last drop of cum out of his cock.
When John finally pulls out, I feel a lot of his cum running down my ass crack and over my balls and cock. And talking about my balls and cock. I was already aching after Mary fucked me. Now I'm damn near in pain. My balls are so swollen, my cock is purple and visibly throbbing.
I looked for Mary once while John was fucking me to see if she would blow me or at least give me a hand job but she was nowhere to be seen. I figured she had her fun and left so John could have his fun. Well, about this time Mary does show back up. "Oh, hell no" I thought. She still had her strap-on on but this time she had a cock that was at least 9" long and at least 3" in girth. There is no way my ass can stretch that much. When she seen my facial expression looking at that cock she knew what I was thinking and the look on her face was "Oh yes, you are going to take this up your ass and there is nothing you can do about it".
Mary came over and took over for John between my legs. If I thought I had a chance of getting my hands free from the restraints I would have tried. But I knew it would be useless. In the meantime, John walked over toward the tv and was fidgeting with something next to the tv.
He came back over and handed Mary something. It was a headband. I couldn't figure out why she wanted to wear a head band. I looked back over toward the tv to see what John was fidgeting with earlier and what the fuck. Is that a camera next to the tv? Have they been recording this? All of a sudden I felt a tennis ball pressing against my ass. It was actually just Mary's massive cock head but it might as well been a tennis ball. I seen John point a remote to the tv and the picture switched from the DVD that John put in when I first got here to a live feed from a camera that is in Mary's headband.
Whatever Mary looks at also shows up on the tv. Well, looking at the tv, I could see that massive cock head pressing against my ass. Mary pulled the cock back a little and John poured a lot of lube on my ass and all over her cock.
She then pressed that damn cock up against my ass again and slowly start pushing. I resisted at first squeezing my ass as tight as I could but the more I resisted the harder she pushed. I figured the best bet for me was to try to relax as much as possible and hope I don't get split in two.
As I relaxed my ass I glanced up at the tv and I could see my ass slowly stretching over that cock head. Visually seeing my ass stretch around that cock made it much worse. And when I say "it" I don't know if I'm talking about the pain or the pleasure. They say there is a fine line between pain and pleasure. Now I know what they are talking about. I couldn't keep my eyes off the tv.
It was mesmerizing watching my ass stretch like that around that cock head. As the head just fully enter my ass I could see my ass closing up around the shaft just under the head.
Mary then started pulling out and I could see again my ass stretching out again around the base of the cock head.
It was actually a site to see. She pulled out pretty quickly and her husband poured a lot of lube into my ass before it totally closed up. She then started the process over again and pressed her cock against my ass and pushed it back in. It went in a lot easier this time. I happened to take my eyes away from the tv and looked at her and she was just grinning ear to ear. She knew I was loving this. Mary kept slowly pushing her cock into me at a very slow and steady pace.
John was keeping her cock and my ass very lubed up. My eyes were glued to the tv watching my ass stretch more and more around that cock as the girth kept getting larger and larger.
I believe there was actually more pleasure than pain now. Hard to tell. And speaking of hard, omg, my cock was sooo swollen and throbbing I don't know how much more I could handle. Something had to give, and pretty damn quick. And Mary had her cock only about 4" in my ass right now.
I don't know what was more agonizing, that giant cock stretching out my ass or my own cock so swollen ready to explode. I don't know if my mind wondered off thinking of all this or maybe I passed out for a few.
Don't know. But looking at the tv I realized that she had all but about 2" of her cock in me. And the grin on her face. She was loving this. It didn't take much longer for her to push the final inches into me. She just stood there and gyrated her hips so her cock would ever so slightly move in my ass.
While Mary was doing this John started to slowy massage my balls and stroke my cock. It just took a few seconds and I was literally exploding. I came so fucking hard. I must have spurted hard at least eight times with each spurt going past my head, on my head, on my face and in my mouth since it was wide open with the ectasy I was in.
With each spurt my ass clamped down so fucking hard on that cock that was in my ass. I don't know how I didn't pass out.
After the initial hard spurts I had a few little spurts that landed on my chest and stomach. John wiped up my cum in his hands and started rubbing my cum all over my cock and balls. He then leaned over and started licking my balls and then slowly ran his tongue up the length of my cock.
He then flicked his tongue on the base of my cock head and slowly encircled the head of my cock with his lips. I'm glad I'm healthy because I don't know how I didn't have a massive heart attack with all of this. While John started slowly engulfing more of my cock, which by the way was still hard as a rock, Mary started slowly pulling her cock out of my ass. John started picking up the pace some and with him using my cum as a lube the sensation was unbearable.
I felt like I was about ready to cum again. When Mary had all but the head of her cock out of my ass, John shoved my cock all the way into his mouth and started deep throating me. When Mary pulled her cock head out of my ass the sensation of both was too much. I came hard while John was still deep throating me. As I was coming he started bobbing his head up and down my cock spreading my cum all over it again. I didn't come as hard this time but it was still probably ranked #2 of my all time orgasms.
He kept sucking my cock until it was totally limp. I don't know if I passed out or just crashed from exhausting but I woke up a few hours later laying on their couch. They were both there looking at me with the biggest grins on their faces. As I was leaving, Mary said the next time I come over she will have to pull out her big boy.
Those last night were just her training cocks. I haven't been back since. At least not yet.