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by DKink (NJ)
Nearly three years after my divorce, I matured and processed thru that pain and at last believed I was ready to start dating again. There was this very attractive woman in a community group I belonged to and we nurtured a friendship for months.
Then on one sunny afternoon things just happened and we began a short lasted, but very hot while it did, “relationship” of some sort. I have to say that it was the most enjoyable sexual relationship I’ve ever been in, I suppose the same wasn’t true for her or perhaps Jamie was looking for more stability but for whatever reason, we stopped having sex.
We remained close friends. But a strange thing started: We eagerly shared stories of our sexcapades with new people. That really turned me on, and obviously her too, otherwise we wouldn’t have been calling each other. I told Jamie of the several ladies with whom I had been involved. And she told me about her boyfriends and how they performed.
While my ex-wife did tell our counselor that our sex life was the best part of our relationship, over time I found it limiting. So when during our first time in bed this beautiful woman gave innuendos of her love for anal, I was all over it.
For years after we stopped dating, nearly every time I jerked off, it was me thinking of Jamie’s magnificent ass. I mean this ass was terrific! I would bring myself to climax just thinking about my tongue licking that beautiful pink skin making it glisten.
She knew all about it—because I told her. That rekindled our correspondence. We chatted more often for a while but as she developed a succession of more serious relationships with other guys, we drifted apart, sadly.
A woman I had just started screwing around with wanted to peg my ass. I let her toy my ass AND I LOVED IT !
Then we went to an adult store together and she bought us/her a strap on kit. I loved the feeling of being dominated, but not handled. I liked how her strapped on dick felt as she went deeper and deeper in my ass. She also toyed my ass with vibrators, plugs, her hand, and prostate massagers.
We would go on buying dates for new toys for my ass. I was getting hard in the stores as she would whisper her intentions and tell me we should get this one or would I like to ride that one. This woman was like the sugar momma to my anal pleasure. She bought at least a dozen toys for my ass-some for her and some for me to get ready for her.
She loved being in the giver role. I loved having her fucking my ass from behind doggy style , as well as facing me while holding my ankles up in the air. Then one day she gave me girly panties to wear-I wore them but from that point she became very domineering in all aspects of our “relationship”. To the point of stalking me and going overall batshit crazy. So I determined the best course was to try to get out of that relationship gently. I should have brought her up on vehicular assault charges but I didn’t. It didn’t end well but it ended.
Jamie had to start wondering about me from telling her all about how I loved being pegged. I also told Jamie how one woman I was seeing really liked to snowball mycum back to me. It only took her doing that twice to me for me to start wanting it. It was so hot kissing her cum filled mouth and making our tongues wet with my cum & I really started to like doing this.
After that I was left with a drawer full of toys...which I proceeded to use with gusto. At some point I started watching transsexual porn-shemales and such. I fantasized to amazing climaxes with plugs, vibrators, dildos, massagers, anal beads & using my fingers to toy my ass.
The thought of a pretty hot woman with a nice big cock had become my obsession. I lusted over their hot asses and how it would feel to penetrate them. Very quickly I began fantasizing about their big juicy cocks and thought about taking them in my mouth and my ass. I started licking my cum from my fingers occasionally, and I always lick up all my pre-cum.
So after plugging my ass for over a year, the other night I called my friend Jamie to invite her for fresh fish & lobster I had caught that day...She could never say no to fresh fish. Now I had been thinking about sharing my new found sexuality with her for a while (Like 6 months) but I wasn’t ready to yet. But for some reason, perhaps it’s because we feel we can share just about anything with each other, the thought crossed my mind as I was slicing the sashimi.
So I just started telling Jamie that I have this new found alternative sexual thinking and that it certainly has something to do with my first sexual experience as a teenager. It was awkward coming forward with this but I pushed on. I told her of how from age 14 to 18 I had gay sex with my neighbor and we loved it. My fuck buddy and I would meet, suck, fuck, and swallow sporadically.
Sometimes we would sleep over and go at it all night. We also wore panties and stockings and swallowed each other’s cum every time, except when we filled each other’s asses. We had bi-sexual 3 ways with a girl a few times. What I remember most was how it felt when my buddy would fill my ass with his warm cum.....that sensation was amazing!
That period in both our lives ended as we went off to college.
So that night after Jamie & I finished the lobster, I showed her pics on my phone of hot shemales and their beautiful cocks. I told her I wanted one of those in my mouth again and maybe even take a nice hard cock in my ass.
She wasn’t totally shocked as I guess my more recent conversations with her may have eluded more to me pleasuring my ass then my cock.
Previously we had exchanged sex pics & vids and watching her sucking her bf’s cock got me so hot. I fantasized about being in her shoes and me playing with his dick. Then this night I found out what I thought was her comment: “You’re next!” Actually turned out to be his comment...what did he mean? Did he want to watch her go down on me or did he want my lips around his cock? I still don’t know the answer to this one.
After she heard my story and my desires she strongly encouraged me to pursue them. She asked me what kind of guy I liked. I said one with tits. She asked what about a really feminine guy? As we talked about it, my cock was dripping with pre-cum. My panties were soaking wet. She totally wants me to go suck some cock and I am ready.
I owe this girl a tremendous amount of gratitude for being such a good friend and confidant. Now if I could just get her to come cruising with me, pick out the right cutie, then watch me go down on my first throbbing cock in 35 years.
Thank You Jamie,
Now go find me a cock to suck!
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