A Boy Named Alice

This is a true story that happened in early March of last year. I had posted it on another blog a month or so ago but it did not get much interest there. I was surprised because this other board is well haunted by sissies and homosexual activity there is endemic. This story has homosexual activity though I certainly do not consider myself gay. I am a dominant and get off on being served.

As you may have guessed, my wife is a submissive and for the past 20 years I have enjoyed sharing her. However, like most submissive women that I know, she tends to be shy, self conscious and quite jealous of seeing me with other women (or even men). So, outside of sharing my wife with other men, most of my play time has been of the "don't ask, don't tell" variety.

My wife, Anne, and I go to the famous swinger resort in Jamaica H2 twice a year and have done so for the past two decades. Over those many years I have developed many, many stories to tell. One would almost have to avoid having fun to not come back with a story. My H2 stories usually revolve around taking a walk in the woods with someone else's wife or running across a happy couple in the hot tub. This story is quite a bit different and I thought a lot of fun.

Our long time friend Bart came along this past trip to H2. Bart is 2 years older than me and, at six foot two, he is 2 inches taller than me too but whereas I am a bit of a hard body Bart is mushy. Because Anne is attracted to people like me she is really not attracted to Bart. Also, I get along great with Bart because he is a submissive pleaser type and I am a dominant taker type. However, even though he is not her type, on three occasions over the past ten years she has let him have sex with her. On all three occasions all three of us were very keyed up with party favors and *******. But I get ahead of the story because, at first, Bart was not the sissy cocksucker. Alice was.

So there we are at the infamous resort and it was near midnight on Sunday. I ask Anne if she is interested in going up to the cafeteria for a midnight buffet hamburger. No she says and rolls over to *****. I call Bart on the phone. Bart is staying in another room on the other side of the resort. He says that he would love to have a burger and we plan to meet in 5 minutes at the common cafeteria in the center of the complex.

I put my shorts on and hang the key around my neck give the wife a peck and head out the door. We were staying (for the first time) on the prude side garden. So it was with some surprise that I noticed all that week that many couples left the door open while they were fucking. This of course is an invitation to knock at H2. I just did not expect to see so much of it on the prude side. Anyway, I head out the door and down the corridor to the stairs when there is an open door.

Standing in the door is a young man with a thin blond beard dressed in a plaid skirt and white blouse. I had seen him earlier at dinner and thought nothing of it because it was "little school girl" night with the large group that had booked that week (various travel agents put on special events). So lots of people at dinner were dressed as little girls. But seeing him standing in the open door smiling at me was a little different than being dressed at a goof ball costume event.
The "little school girl" was in a pleated skirt and wore bobby sox and pumps. Even in his heals he stood no higher than my chin. He was (guessing here) thirty five years old and had a thick head of sandy hair long enough to cover his ears. I could see his bra through the thin white material of his blouse. He was slight of build and actually looked good in the flaring skirt.

I am 55 years old, six foot tall and a large (but not fat) frame of over 200 pounds. My very short and thinning hair was once black but now is mostly gray. Combined with my exercise program and my Italian heritage I have often been compared to a gladiator (or a boxer). I do have a large cock and it is very dark in color compared to my olive skin.

But back to the "little girl"...

So, as I walk by I complement him and ask a question.

"You look very pretty little girl. What is your name?"

He looks at me then lowers his eyes to the ground and says "Alice".

"So are you here alone Alice?" I ask.

He says "No, my wife is at the hot tub".

This is H2 code talk "for my wife is out slutting around and has left me here alone to think about it".

"So Alice" I say, "is she with her boyfriend or looking for new cock?"

"We are both hoping to find someone to please" Alice says.

At this point I had half a hard on and am in a rush to go meet Bart up at the dining room so I get very direct.

"Alice" I say, "would you like to suck me?"

"Yes please" he says.

Worried about Anne waking up and then looking in on us I said "Okay, but with the door closed."

"Yes sir" says Alice.

I go into their room and kneel on the bed. The cute little school girl comes over and sucks my cock. I get hard and cum into his mouth in about 2 minutes.
When Alice sucked me off I was up on my knees and he was lying on his side. I held his head with my left hand and played around under his skirt with my right. I very much enjoyed his moans and whimpers while he sucked. I just kept saying "good girl" "good girl" and fucked his mouth with my hip motion. I came quickly as I did not even try to hold back. I said something like "I'm cuming in your mouth now girl" as I spurted. I don't spurt a lot of liquid like in my youth but there was enough for him to swallow. He hummed as he held his mouth on my cock while I finished. He mumbled some kind of thank you as I pulled out and put my shorts back on.

By the way, when I played around under his skirt I could feel through his panties that his very small cock got harder and harder as he sucked me. I took it between two fingers (through the material of his panties) and squeezed. By the time I finished off in his mouth he was rock hard. I left him like that on purpose.
"Thank you" I say and headed up for a burger.

I left Alice standing in his outfit at the door with a smile on his face. I wish that I had invited up for a burger. Must have been their last night cause I did not see him again.

I love this kind of action because I can be totally selfish and just let go an cum and do nothing in return. I think Alice liked it that way too.
So I get to the dining room and tell Bart the story about what had just happened. I had expected Bart to want to run down the hall to get his own blow job but instead, and I was not too surprised, Bart tells me his submissive fantasy of being fluffier and clean up boy.
So two days later, Anne, Bart and I are naked and getting high in his room. In the times that Anne has had sex with Bart it has been anal sex. Anne loves anal but will not take me there due to her fear of permanent damage but Bart truly has a teeny tiny cock that barely shows past his pubes. Things are really warming up and the wife and I lie on Bart's bed and start kissing and start fingering her. That she would do this in front of Bart is a definite single that she is game for play time.
I single Bart to come up behind Anne so that we would have her sandwiched on the bed. Instead he comes up on the bed and kneels and calls me Master and Anne Mistress and asks if he could be our oral slave.
Well, the mood was right and the timing was perfect. What the hell?
Afterward Bart felt humiliated and embarrassed. So, in sympathy Anne let him fuck her pretty blond pussy.
It was a great night and a great week.
By the way, I am not superman and cannot cum three times a day like in my youth but I can still cum every day and sometimes twice a day. So, later that same night that we were with Bart the wife again goes to ***** and again I go wandering the resort alone. This time I run into another set of friends of ours named Molly and Jack. Jack has been impotent for the past six or so years and has shared Molly with me on a few occasions. This night Jack leaves me alone with the small and beautiful Molly.
Molly and I took a walk through the woods...
MD