I couldn’t believe it!  I was offering him the most intimate part of my being, willing to allow him to fuck not only my well-used pussy, but also my nearly virginal ass. However, it wasn’t quite that simple and as he explained it began to make more sense.  He wasn’t willing to try and imitate someone else’s experience, but he was willing to try and pleasure me if I was willing to just allow thing to happen as they would without a set routine or game plan.  I didn’t know it then but I was to learn later this was the most important secret to good anal sex.

Meeting Thomas for the first time was scary primarily because I don’t generally meet guys knowing that they are going to be taking me rectally, but in this case I’d already emailed exactly what I wanted.  On top of this I had these incredibly hot stories I’d masturbated to for weeks of him totally dominating and pleasuring a young woman, so I imagined him as some special sex machine, however he was – well like me in the murky 40’s, carrying a little extra around the middle, good looking in a average way, and very, very tall.

We met for dinner and as he seating me his hands slid over my breasts making my nipples hard instantly, but he seemed unaware of what he had done and he was a perfect gentleman throughout the meal, flitting with me, some double meanings and sexual innuendos, but all of it fun.  By the time the meal was ending and we were lingering over coffee I had decide to sleep with him and yet he never seemed to sense the need to ask me, he simple said,  “It is getting time we head back to our room.”  All I could do was weakly nod and follow to his hotel.

He is very oral and by the time he had me naked there were few places his tongue had not visited or probed.  My nipples tingled with the memory of his warm mouth closing over their hardened tips and I could still feel every place he had contacted as his mouth tried to kiss every inch of skin exposed on my buttocks and ass crack as he’d slowly removed my panties following them all the way to floor along my inner legs with wet tongued kisses.  Laying me on the bed her brought me nearer and nearer climax working his skilled mouth over my labia and anus alternating back and forth the only man ever to probe inside my ass with his tongue filling me with odd and desperate longing to do wicked things I never before desired until I thought I never be able to stand it and then he entered me.

Sex with Thomas was not all that unusual, other than the fact that he was very long lasting and fucked me for a good 30 minutes without either of us climaxing shifting from missionary to me on my back and he on his side entering me, then taking me from behind, and eventually back to missionary my legs up and back enjoying him in my depths when suddenly he pulled out placed his organ’s tip at my anal entrance which was completely soaked with my own juices and entered me.

The feel of his rubbery firmness separating my anus opening was both frightening and arousing.  Every other man had asked me if I was ready and had gone slowly but he was at least halfway inside of me and I tried o warm him, “careful….” But the next instant he was fully inside me, and the moment after that thrusting me in long complete thrusts as the length of his organ slide easily in and out of my asshole. I could only wonder at the pure spasms of pleasure that washed over me with each thrust wrenching from my throat the most ardent sounds of feminine pleasure.  Pleasures I had never know I was capable of from such an act controlled my body and I could feel myself building rapidly toward my own release.  My voice, raised just moments ago to try and stop such penetration now begged shamelessly for more, “Oh God!  Please.  Don’t stop, oh God, I am going to cum, don’t stop, God, Fuck me harder! Now” Then it happened!

Contractions began and wave after massive wave of pleasure ripped through my whole being, warmth washing outward in waves as my anus clung with every spasm to his naked cock trapped inside of bowels while my empty vagina literally poured my arousal out of its opening with each new wave of pleasure and somehow amidst all this he continued fucking my asshole and his own orgasm was coming. 

After another minute he filled my ass with his emission then he pulled me to the side and still in my ass began to fuck my now flooded passage his hand cupped my pubic mound in the massive outpouring of love juices and sliding easily over my sex, my moans timed to the still hard cock which was possessing my body and gradually as the minutes pass I become aware that my arousal is building and that I am going to cum once more this time brought off by the gently teasing hand and the forever lasting cock in my butt.  Just as I near orgasm his fingers find my center of pleasure and I explode instantly and repeatedly as he takes me and uses me for his pleasure, his fingered hard on my throbbing clit as over the next 15 minutes he fucks me until another load of maleness is left inside my anus.

Laying on the hotel bed, covered in perspiration I contemplate why Thomas could pleasure me when others could not.   Most of it had to do with timing.  He never asked to fuck me in the ass he just did it, never letting me tense up.  I mean what can you do but stiffen up when you loved asks if he can fuck you up the ass?  Similarly once started he didn’t let me get tense like others had trying to be gentle.  Hesitation was not gentleness because it delayed my pleasure and in the end prevented my enjoyment.  Thomas had made me climax in ways I could never have imagined because He sensed what I wanted when I was not even sure what I wanted.  Thanks to Zoke’s story I wrote another new chapter in her legacy at age 45.  I wonder who will be next?

 

Questions, comments or suggestions or volunteers contact:  Thomascan06@yahoo.com

 

 

(me) truth or dare?

(Cindy) dare

(me) I dare you to lift up your shirt

Cindy blushed at first but didn't hold back as she lifted up her shirt showing me her small boobs with hudge nipples and now it's her town.

(Cindy) truth or dare?

(me) Truth

Cindy protested saying that's not fair so I took a dare.

(Cindy) I dare you to lift up your shirt

I did then it went even further

(Cindy) I dare you to show me your penis

Being shy I hestitated but then showed her which at the time was hard and so it was my turn.She took the dare again.

(me) I dare you to show me your vagina and ass

Oh my did she ever.

It went on like that for us for a couple of years before we got bolder at the age thrt-teen when I lived in a new house that had the oldstyle basement with the cellor door outside as we went in. She was talking about looking at her dad's porn mags which showed a man in a woman's ass and she told me she wants to try that. Not having any sexual experience I didn't think that was possible but I found out that day it is and been hooked on anal sex every since. 

The basement had stone brik walls with a dirt floor and we were sitting on a blanket facing eachother. I reached for her boobs carressing them as she reached for my cock stroking it and we kissed on the lips open mouth with our tongues exploring eachother. Shen then unbuttoned and unzipped my pants pulling my hard cock out and she touched the head with your tongue. Never experiencing anything like this I jumped and she looked up at me saying "relax." Guessing from her skills, I figured she had done this before because it felt damn good for a blowjob and I couldn't help what happened next as I shot my load into her mouth. Thinking it was over but not by a long shot as she clamped her lips down my cock firmer and swallowed my cum to the very last drop. Wanting to return the favor I asked her to lay back which she did legs spread, I layed on my stomach and imediately started using my tongue on and in her pussy, of course I wasn't doing it right at first but she was patient with me letting me know when I was touching the right spot as she came hard with her hand over her mouth trying to muffle her screams. Then outside her parents were calling for her, we both smiled at eachother , got dressed quickly and I seen her off with her parents.

The next time she came over with her parents, we immediately went to the basement kissing and touching eachother again. We both admitted to eachother that we missed eachother and been looking forward to our time alone again. She then got a smile on her face, I asked her why and she said "you remember shooting stuff in my mouth and I swallowed it?" Of course I remember, how does a teen boy forget something like that? She proceeded to say "I want that to happen again but in my....ass." Of course I was puzzled not knowing how my cock would fit in such a tiny hole but must admit the thought did turn me on as I felt my cock hardening. 

I spreaded out the blanket as she was pulling her shorts down along with her panties, then got in doggy position and looked back watching me pull my shorts down as my cock sprung out in the open. Smiling at the site she said "I want to feel it in my ass, please." Not sure what to do, I asked how the couple did it in the mag and she instructed me on what she had seen. So, I'm on my knees behind her admiring her ass while bringing my cock closer to her asshole and we both gasped as the head of my cock disappeared into your asshole and since we had no lube, I took my time when she asked me too until I was finally balls deep as we both are panting heavy and she tells to go slow at first which I did. Both of us panting even harder as it was feeling good for both of us I was by now fucking her ass faster. Cindy moaned but in pain, instead with pleasure and talked dirty to me which she didn't need to as her ass was feeling good taking my cock but her dirty talk did add to the good feeling we were experiencing. I grabbed her hips pounding my cock in/out, in/out of her asshole and she was matching my every thrust with her moans, my heavy breathing and sounds of our bodies slapping loud enough for us to hear.All this became too much for me as I stopped moving as so did she while enjoyed the feeling of my cum filling her ass up. By then she was laying on her stomach, I was resting on her back with my cock in her ass pumping load after load of cum deep in her ass and we managed to kiss with my cock still in her ass.

After getting dressed, we heard her parents calling for her as we snuck on last tongue filled kiss and as we made our way outside, both her parents and mine were standing there with a look that told us we were busted and of course we tried to deny anything they were accussing us of.  It's been a long time of her parents not bringing her over which was driving me crazy, I wanted in Cindy's ass again as she later told me she wanted it again much as I do but that's a different story.

 If you want to read our second encounter, give me your feedback on this story that acctually happened.