Very Unusual Date

Taboo
2008-02-13

Topic: This started out as just a nite out with an old girlfriend, dinner and some drinks.   Sarah, was a single mother of a teen son, we met thru a mutual friend a couple of years ago , and dated about a year, nothing real serious. Well, we ran into each other a few weeks ago and exchanged numbers and BS, and went on our seperate ways. Well, here she calls about a week ago and invite's me to dinner, I liked Sarah, and we had great sex, even a three way(MMF) with a friend of mine, so I accepted, and we set a date and time.
Well, the nite came. I picked her up about 8 and we went to dinner, and then sat at the bar and talked about old times.
The talk soon turned to sex, and she asked me if I would do her a favor. Of course I agreed, I hadn't even heard what she wanted yet, but she asked if we could go back to her place first so we could "Loosin' UP", with some more drinks.
I couldn't leave the bar soon enough, we got back to Sarah's house, turned on some tunes, and got some drinks, and went to the couch. Sarah, excused herself to put on something comfortable, she returned in a Tshirt and gym shorts, she knew I liked that.   She came over and sat next to me and thanked me for coming over. We started to make out, now I know she planned it this way, to get me going and then ask the favor. She stopped kissing me long enough to ask me her favor, "I would like to have another three way with you and someone I have picked out. " Sarah, asked?
Of course, I  again agreed, without giving it much thought, "Sure, can I ask who the third is"?  And of the darkness of the hallway I hear, "Me", it's a real surprise to me when out of the darkness comes, Jake, Sarah's, son. I couldn't speak for quite a while, it seemed like hours. Then Sarah broke the silence by telling me that Jake was having trouble with his sexuality, he had had some girl friends, and a little oral sex with one girl.

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   She told me she knew I was ok with some bi action and hoped she would be able to convince me to give her son a taste of sex with a guy. Jake was struggleing with this because he was affraid of what his straight friends would think, so his mother offered to help. Jake aggreed with his mom on me to be the one because he did know me from before, but this boy was young. Sarah assured me that she really wanted it to be someone she knew and trusted not to hurt Jake. Sararh made sure I agreed by pulling on my dick the whole time she talked to me about it. It didn't take much even though I knew it wasnot right, but they assured me that Jake wanted this. I agreed, and we all went to the master bedroom.  
As we entered Jake asked if we could take a shower, I agreed, and didn't even notice Sarah wasn't even in the room yet. We went in the bathroom and I began to remove Jake's shirt, then his sweat pants, he was wearing boxer shorts, but he couldn't hide his erection.   I pulled off his boxer's to expose a nice, maybe 5in. cock, with sparse blonde pubic hair.   When I began to undress I realized Sarah was watching it all through her camcorder. I got naked and started the shower, it was huge, it even had a little seat in the corner. Once warm, we got in, and Sarah followed with her camera, we had often taped our sex sessions before, she knew I was OK with it as long as I get a copy.   Knowing Jake would be a little tentative, I tried to start things, I grabbed the soft soap and got a good hand full and began to wash Jake's trembleing body.

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   When I finally got around to getting below his waist, he let out a little yelp.   His cock was rock hard and dripping with pre-cum, when I began to play with his asshole, he shot a load right then, he was a little bit embarassed, but Sarah and I assured him it was ok, and he would recover quickly. After a little laugh about it, I asked Sarah and Jake, since he didn't have alot to begin with, if I could shave his pubic hair. Oddly Jake agreed without question, and Sarah said she didn't care as long as he was OK with it.   I put Jake on the little chair so the water wouldn't wash off the shave cream. I smeared on some shave cream and went to work, it wasn't hard because his hair was very thin. I asked him to stand, turn around and bend over so I could shave his asshole if it needed it. When I finished Jake began to wash me, only he started with my cock and had to be coached how to finish the shower.
We got out, dried off and went to Sarah's bed, where Sarah had laid out some toy's and things. Sarah had no intention of having sex with her son, she just wanted to watch and tape it.   I laid Jake on his back and just touched him all over to try and loosen him up, he was still shaking.   I told Sarah to zoom in on his cock and with that a began what turned out to be a very short BJ, I don't think I stroked his cock with my mouth more than twice and he exploded into my mouth. Jake appoligized but I told him, after I drained that cute little cock, it was Ok I wanted him to cum in my mouth, and I told him I planned on cuming in his. He looked surprised but said nothing. Sarah, still taping, but now with a tripod, was playing with herself as she wathced the action unfold.

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    I turned Jake over, spread his legs and started to play with his naked balls, I knew his dick was hard again, and I helped him adjust so he was comfortable. I began licking his balls and Jake wiggled and moaned with pleasure. I sucked them together and one at a time. Then I began licking up towards his ass, and I didn't stop. Then I got to his cute little hole. I licked and darted my tongue in and out and around his cute asshole. He came on the bed. Now it was my turn, so I laid back and slowly began to enjoy this young boy's touch. He was unsure what to do so Sarah gave him instruction from her perch near the camera. Jake played with my dick for along time before he would put it in his mouth, but it was worth the wait. Jake took the head and began licking his way down, he couldn't take all of it but he was doing very well.   Sarah told Jake to get on top of me in a 69 position, so I could enjoy this little cock and balls some more. While he sucked me I stuck my tongue up Jake's tiny ass again and when I did he began to cum on my neck and chest so I moved to suck his little cock and the rest of his load. That put me over, I told his I was going to cum, and Sarah moved around to the end of the bed for a better angle, I was sucking his last drops and I finally began shooting my cum into Jake's mouth. He choked a little not knowing how to handle it but his mom encouraged him not to stop and swallow as much cum as he could, and he did a nice job.

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   We laid in a heep for quite awhile, then Jake asked, "What's Next?".   So his mother instructed him to turn me over and begin licking my ass. "Get it good and wet, cause your gonna fuck it". He did, he licked and licked and put his tongue in my asshole. I got on my hands and knees and told him to stick his dick in my mouth so I could get it wet and slippery. He then placed the head of his little dick against my asshole and I told him to push. When he did I pushed back and he went in, it didn't hurt, I've played with bigger dildo's so it wasn't uncomfortable at all. Jack moaned and groaned with every thrust. I asked him to cum in my ass, and I barely got the words out and he was cumming in my ass. When he finished I told him to pull out slowly and lay on his back. He did without question, and I put my balls near his mouth and told him to start licking and I slowly let his cum drip from my asshole. He licked me dry and even licked my ass on his mom's suggestion. Well that just about did it for me I asked Jake to suck me again and I came in his mouth, on his face, in his hair, everywhere, it was great.
Sarah and Jake thanked be a thousand time, but I assured them the pleasure was all mine, and would like to do it again sometime, but we'll see. After a short nap I got up and left Jake and Sarah sleeping on Sarah's bed.

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   What a night. I hope we do it again 
 
 
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