One of the strangest relationships I've had over the years was with awoman named Laura. She saw my profile on Yahoo and dropped me a note. It was like manna from heaven. She was very into the idea of fucking a man in the ass with a strap-on dildo. She'd not done it before but had fantasized about it for years. Would I be willing to help? You bet!
We chatted for a long time before we finally agreed to meet. Her trailer park wasn't too far from where I was staying at the time and I went to see her one Saturday afternoon. She was quite a hefty gal with few taboos. She had me strip down and gave me a pair of crotchless panties to put on. Back in her living room she had me bend over an ottoman and tied me to it so that I wouldn't squirm away as she paddled my ass.
Luckily, I had built up a good deal of trust with her via our chats and was able to take all of the abuse she wanted to give me. There was no ass-fucking that night. Instead, she wanted to be eaten out for a good long while. She was one of those ladies who unleashed a good deal of vaginal secretions when she came. She had me rub my face in her pussy, coating every inch and lapping up what I could.
Afterwards, she had me masturbate onto her bountiful breasts and clean up my cum with my tongue.
The next time we met she had a surprise for me. Laura had invited over "Suzy Cocksucker," an older transvestite. I was put into a pair of white panties (and nothing else) and bent over her couch with Suzy next to me. We looked at each other, smiled, and turned to look forward and steel ourselves to what was to come. The only warning was the whistling through the air of the strands from the cat of nine tails. The question was, "Will it be her or I that get it first?"
"WHACK!" It was Suzy's turn but soon it was mine. Laura went from ass to ass, her flogger singing a sound of pain as it whipped across our pantied bottoms. Back and forth she went, whipping each of us. At times, she would stand between us and caress the pantied cock of the other as she concentrated her whip on the other. When she was satisfied, she bound Suzy and left her kneeling on her living room floor while she took me into her spare room down the hall. I felt like I was the prize slave and this made me smile inside.
In privacy she produced a double-headed dildo which she slid into herself. She had me kneel on the room's bed and got behind me, trying to slide the other end of the dildo into me. It just wasn't stiff enough to do a good job of penetration. I suppose it felt like being fucked with a semi-hard cock. She tried valiantly to get it in and fuck me but it just wasn't the right equipment for the job. Instead, she used a dildo and fucked me by hand for a bit.
We went back to her living room and she bound me over her ottoman as before. Then she gave me a treat that I will never forget and shall always be thankful for. She had Suzy get behind me and perform analingus on me. It was amazing. I've never felt anything quite so nice. Of course, I was very self-conscious. I knew that I was clean but felt awful for being hairy and tasting like KY Jelly. So, even while I enjoyed it immensely I was too self-conscious to just let myself go and enjoy it fully. I hope someday to enjoy this again without the guilt.
Laura released me and had me get down on the floor next to Suzy. We were face-to-cock and performed sixty-nine on each other while Laura watched and enjoyed. She wished aloud that she had a digital camera to capture the moment forever but, alas... When she had had enough, she allowed Suzy to lick her to orgasm while I sat (bound) and watched. She had Suzy get her face wet with her juices and my job was to lick Suzy's face clean. With the taste of makeup, this wasn't a pleasant task.
She was done with us after that. We cleaned up and I said my goodbyes to Laura and Suzy. Little did I know that that would be my last time seeing Laura. She had just started dating a guy and he wasn't into BDSM at all. She felt guilty keeping on submissives while dating so she dismissed everyone who saw her and cut herself off from this part of her life. The real shame is that this kind of thing happens all the time to both men and women. They find that special someone and find themselves having to make a choice between D/s or a vanilla life. As vanilla is seen as "normal" that's usually the one that wins out.
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<a href="https://www.lushstories.com/stories/crossdressing/an-afternoon-with-suzie-ccksucker.aspx">An Afternoon with Suzie C*cksucker</a>