And The Winner Is…

Thank you all so much for your submissions! I had great fun (literally) reading them all and I salute the juicy creativity you offered up to Pegging Paradise. All entrants will receive a surprise email in thanks for your entry. I can tell you all enjoyed Masturbation did I!


The winner is "justabitkinky", whose story below included a very hot fantasy and an equally erotic description of his self-pleasuring. Enjoy! By the way - justabitkinky has an interesting blog he started recently with lovely photos and more erotic writing. You can find it here. Keep on writing, justabitkinky!




The week was long, stressful and without orgasm. I went to sleep late Saturday night after spending hours browsing naughty pictures and videos online. The subject that night was strap-on sex, a passion of mine which I’ve been obsessed with lately.


All it took was the posting of a woman wearing a strap-on in a fetish group and off I went. Google image search was my first destination and by the time I realized the time, three hours later, I was on some porn site watching endless clips of women pegging guys. It was one of those nights though where I kept looking for the perfect clip, the one which I would masturbate to. I was overly tired and just couldn’t settle on a perfect candidate, so I frustratingly went to sleep with all sorts of fantasies in mind.


I awoke bright and early Sunday morning with a painful hard-on. My mind immediately restored to the night before and images and fantasies flooded my every thought. I couldn’t help but kick off my blanket, under which I was wearing nothing but boxers and lightly fondle myself. The head of my cock was poking out right above the waistband as my hand took hold of it through my boxers and my thumb rubbed across my exposed sensitive cock head.


Closing my eyes, my fantasy started to vividly play.


I’m at a spa and receiving a massage from an attractive woman. She is just my type too; average height, in good shape and some muscle tone. While she has a soothing voice, it is very apparent that she has a sensually dominant personality, which I of course love. Starting on my back, she pulls down the sheet to expose my back right down to my butt. Her hands expertly massage my upper and lower back. I am completely relaxed after fifteen minutes of her deep tissue massage when I notice her hands paying more attention to my lower back. Swiping back and forth, from side to side, I feel the sheet covering my butt gradually and subtly moving lower and lower; a millimeter at a time.


The cool air hitting the very small exposed area of my buttocks feel good. I don’t move or say anything so she continues, perhaps thinking I’m asleep. This continues for 10 minutes until my butt is completely exposed, her hands rubbing softly across my butt cheeks. I continue to pretend I don’t notice as I don’t want her to stop. The feeling of her hands exploring my butt is sensational.


My eyes still closed, I remove my boxers and kick them off the bed as I spread my legs wide. My toes curl as I grab hold of my hard cock; pre-cum drooling from the tip which I use to coat the shaft with. I proceed with my fantasy as I slowly begin stroking myself.


She quickly gets more adventurous and with a finger slides up and down my butt crack. This time I can’t help myself and emit a moan as my butt involuntarily thrusts upward toward her now lingering finger.

It seems that response is what she was looking for as she immediately gets up on the table and straddles my legs so that her body is facing my head.


“I see you enjoyed that hun” she says as her hands squeeze my butt playfully.


“mmhmmmmm” was all I could say in response as she spreads my cheeks apart and rubs my asshole on the surface.


“Oh, yes. Good boy. I knew you’d love having your ass played with,” she says as her finger which is coated with massage lotion pokes its way into my asshole.


It seems to slip in quite easy and I immediately feel myself get aroused. Her other hand grabs hold of my balls and plays with them somewhat aggressively as her finger now slides in and out of me with ease.


Within minutes she can tell that I’m on the verge, as I’m moaning and writhing beneath her.


“Turn over, sweetie, “ she says as she hops off the massage table.


I turn over and glance to my right where I see her undressing. She is completely nude within seconds which makes my cock jump with further excitement. Then, I see her open a cabinet and take something out. I can’t really tell what it is as she is facing away from me. I see her stepping into something though which looks like a pair of panties but only straps.


She turns around and I see her wearing a very realistic looking strap-on cock which has to be about 7 inches long. Her eyes close in pretend ecstasy as she wraps her hand around her cock and slowly strokes it, simulating jerking off.


I surprise myself with how turned on this gets me. She hops back on the table and lifts my legs up in the air with ease.


“I’m going to fuck your ass. I know you will like it, “ she states authoritatively as she rubs her cock head along my ass crack.


All I could do was close my eyes and moan. She had me, there was no way I could refuse her now.


“Breath in and out for me sweetie, “ she says, her breathe quickening with excitement.


I breathe in, then out and as I exhale I feel her push her cock head into my tight asshole. I grunt and immediately am in love with the feeling of being completely filled. She has me hold my legs up in the air as she quickens her pace, making love to my ass with her hard and thick cock.


My hand is a blur on my cock now, stroking it fast as my hips undulate in rhythm. My other hand is between my legs; alternating between fondling my balls and a finger slipping into my excited asshole.


Imagining a woman taking control like that and fucking my ass stimulates my mind like nothing else. My legs bend inward as the base of my feet touch each other. I can’t hold back anymore. A seemingly endless amount of cum spurts from my cock landing all over my stomach and chest.


The orgasm is so intense, all I could do is lay there covered in my cum just wishing a woman was really there to lovingly fuck my ass!

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