tagBDSMA Boy's First Time

A Boy's First Time

bytheredheadboy©

I've been 'kinky' since as long as I can remember, writing erotica since my mid-teens, and had been indulging in D/s play with otherwise vanilla girlfriends for some time. Eventually though, at about age 20, I found myself single and resolved to get out and meet other kinksters.

At a munch in London I was soon approached by an older Domme, in her mid-30s perhaps. We chatted for some time, and at the end of the evening she invited me to come visit her that weekend.

This was to be my first experience with a 'proper' Domme. As I mention above, I write a lot of - primarily Femdom strap-on - erotica, some of which you can see on my blog on this website. However, I have tried to write this with a more factual tone, whilst keeping it interesting. I've also tried to remain strictly accurate in the telling, but several years have passed! Like any such moment though, it is still etched quite clearly in my mind.

Enjoy, Red.


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We met in a pub that Saturday, and had a couple of drinks as we talked, and got to know each other a little better. After the second, she announced that she had confirmed that I "wasn't a dick", and that she would take me back to hers!

When we got there, she gave me a suppository, a jelly enema capsule, and sent me off to the bathroom. When I had returned a while later, she had changed her outfit. She wore black nylon stockings, lacy black knickers that hinted at the shape of her womanhood, and a black and burgundy corset. Fixing me with a stare, and a sly smile, she told me to undress completely, part my legs, and bend forwards.

The point of no return! I was shy, but it was what I wanted. No, needed. I did as she commanded, and heard her move behind me, squat down, and felt her breath on my buttocks. She had instructed me to remove all hair from my scrotum and bottom ("I like to see what is mine"), but had announced that she liked my red hair, and that I should keep it nice and trimmed above my penis. "Well done," she commented, observing that I had followed her orders.

She had me lie down on my back with my bottom at the edge of the bed, and then pull my knees up and apart. She then knelt down at the bottom of the bed. I remember blushing, but a thrill running through me. I had never been so exposed, and I could almost feel her gaze running over my cock, my balls, down to the object of her desire.

"What a pretty little hole you have" she told me.

I blushed deeper, mumbling, "thank you Mistress" in response.

I shuddered, a low moan escaping my lips as I felt her fingertips between my open buttocks, teasing me, lightly brushing my hole. My anus has always been a very sensitive spot, and she could tell right away I would be putty in her hands. A lubed fingertip was placed against my hole, and she gently massaged my sphincter, until it began to relax, then she gently slipped her finger inside me, pushing it in to the joint. She slide its full length in and out of me for a few moments, before placing the pad of a second finger against my entrance, pushing it easily in alongside the first.

Then her finger motions took on a different pattern, as she curved them upwards, using a beckoning motion to find my prostate. I groaned loudly, pushing my hips up as it was touched for the first time in my life, and my cock, which had been resting hard against my stomach since she had first begun to stroke my bottom, began to leak pre-cum.

Satisfied that I was relaxed, she took a smallish dildo, about 6 inches in length, and having lubed it up, pressed it against my anus, slowly sliding it up in to me, until I had taken the whole length in to my rectum. She slowly, and skilfully began to slide it in and out of me, twisting it as she did so. Throughout she praised me, telling me how wonderful I looked, how beautiful my anus looked stretched tight around the shaft of the dildo, of all the ways and positions she was going to fuck me.

It wasn't long before she slid the dildo out of me entirely, looked me in the eye and said "you know, I think you need something a little bigger".

An almost identical, but slightly larger dildo was produced, and again pushed deep in to me. Again, it felt very comfortable, and she teased me "you little slut, you tell me this is your first time, and your hole is taking everything I give it!"

With a wicked grin, she walked to a shelf and came back with a third dildo. She stood over me, letting me see it. It was thicker than the other two, slightly thicker than a good-sized penis, and about 7 inches long. Made of black rubber, its shaft was ridged, in a similar way to anal beads. She smiled down at me, evidently pleased, and I felt happy to be pleasing her. Leaning down she kissed me deeply for the first time, her free hand lightly caressing my by now throbbing cock. I returned her kiss hungrily, I had never been so aroused, needed anything so much.

She moved back between my legs, and told me to keep my knees up and apart, and to spread my bottom open for her. I blushed again deeply; I'd thought I was exposed before! Readily though I took one of my buttocks in each hand, quickly obeying her as she purred, "that's it my darling, nice and wide for me".

I could feel the cool air brush over my anus, still slightly open in a round 'O' from the two smaller dildos. The cool feeling was quickly replaced by the feeling of the head of the beaded dildo pressing firmly against me. She leant down and placed a single soft kiss on the tip of my own cock, causing it to jump off my chest. Locking eyes with me, she pressed forwards firmly, and I tipped back my head and moaned in pleasure as the head slid past my tight sphincter and in to me.

"Good boy, what a delightfully accommodating bottom you have" she purred, eyes focussed on the black shaft as it slid smoothly inside of me.

I could see how turned on she was, and I filled with pride at having pleased her. She watched with barely described lust as my rim stretched and contracted around each ridge in the shaft, pausing briefly before pushing the next one in to me.

Finally, the flared base of the dildo was pressing against my opening, the crinkled skin of my hole stretched smooth around the thick shaft, every inch inside of me. I had never felt so full, so right. She asked me how it felt, I told her wonderful. With a smile she took my erection - it had never been so large! - in both her lubed hands, and began to masturbate me. Never before had a woman touched me this way, as she used both hands at once in the 'basket weave' technique to manipulate my aching cock. I could feel the muscles in my bottom clenching tight around the shaft embedded in me, as I quickly neared orgasm.

Abruptly she stopped, squeezing the base of my penis to stop me cumming.

"Not yet darling" she said as I moaned in frustration, her hand dropping to grip the base of the dildo protruding from my parted buttocks.

Slowly at first, then faster and deeper, she began to fuck my virgin hole with it. The sensations were overwhelming as I felt my muscles stretch and contract over the ribbed surface.

After some time she pulled it out entirely without warning. The sudden feeling of emptiness overwhelmed me - I knew then that I was destined to be a submissive boy-toy to a strap-on wielding woman for the rest of my days.

She turned away from me and walked to her dresser, picking up a strap-on dildo harness from the top. Keeping her back to me, she hooked her thumbs in to the waistband of her knickers, pushing them down over her hips, and off her legs. I mumbled incoherently, my eyes drawn to her beautiful bottom, desperately willing her to turn around and give me a view of her womanhood. She denied me though, teasing me, as she kept her back turned, looking back over her shoulder at me as she pulled the harness up her legs. I could see that the harness had two small plugs that fitted between the wearer's legs; their use obvious. As he pulled the harness up tight between her legs, images of them pressing in to her own holes filled my mind, and it was all I could do from taking my cock - which had stayed erect the entire time - in my hands and wanking furiously.

She turned back towards me, the smooth, shiny surface of the strap-on jutting out from between her legs. Walking towards me, she put some lube in to her palm, and began to lubricate the shaft, stroking it as if it was a real cock. Kneeling, she took my legs, and placed them over her shoulders, shuffling forwards so the head of her strap-on was against my skin; my hole was still open from the dildo so the tip of her strap-on rested just inside of me.

"I will be your first, and you will always remember me" she said, looking directly in to my eyes. "We have the rest of the day for me to show you all the wonderful ways you can use your gorgeous bottom to please me. Later, you're going to put on a little show for me, and if you're very good, and it really turns me on..." she paused, leaning forwards a little, the head of her strap-on pressing a little further past my opening, "I'll masturbate for you whilst you fuck your own bottom with one of my dildos. Would you like that?"

"Yes" I moaned, "I want you so much, I've never wanted anything so badly"

She chuckled, "where has our blushing virgin gone? Tell my sweetheart, tell me what you want"

I had no doubts now, no shyness, I was in lust; "Please Mistress, please fuck me, fuck my anus, show me I am your boy, teach me how to serve a woman"

She chuckled again, and pressed forwards firmly with her hips, and I threw back my head and cried out as she pushed forwards until her belly rested against my swollen balls. This time, there was no gentle build up, no sexually interested examination of my anus, she went straight in to fucking me. My legs over her shoulders afforded her full entry, and she made sure not an inch was wasted as she thrust in and out of me. I couldn't believe the pleasure; my whole world focussed on my anus. I could only gaze helplessly up at her, and at that moment I didn't think I'd ever seen a more beautiful woman, I was her slave utterly.

I don't know how much time passed before she slid right out of me, and that desperate feeling of emptiness returned. Patting my bottom she ordered me on to all fours, telling me to lower my shoulders to the bed so that my bottom was "nice and high" for her. I quickly complied, eager to have her inside me again. She climbed on the bed between my legs, and guided the lubed shaft between my buttocks. It slipped easily in to my hole, and she resumed her fucking instantly. My thick cock was swinging back and forth as she fucked me, her hands on my hips, pulling my body back to meet her thrusts. We were both panting now, sweating, frenzied hip movements. She reached underneath me and began to masturbate me in time with her own thrusts.

"Cum for me sweetheart, be a good boy and cum for me with my cock filling your bottom" she encouraged.

Every thrust of her hips pressed the head of the strap-on against my prostate, and her hand twisted up and down my shaft. It didn't take long for me to cry out, and the most intense orgasm of my life to overtake my entire body. My toes curled, my body tightened around the invading shaft buried deep in my backside, and I came hard - large amounts shooting out of my throbbing cock on to the bed.

She slowly milked me dry, her hand tightly squeezing up and down my cock, as she slowed her thrusting in to me. Wrapping her arms around me she nudged me on to my side, following me, still buried deep inside me. We lay there, spooning, her body pressed against my naked back, as we recovered, her hand idly caressing my now softening cock, cupping my balls, and I knew it all belonged to her.

We did much much more that day. Whippings, canings, electro and wax play, we used pinwheels, pegs and clamps. I got a thorough education, and every part of me was used!

The show she'd said I was to perform was still to come though...

At the end of the day, after we'd relaxed, she produced a large, anatomically realistic cock, with a large rubber base. She placed this on her wooden floor, and I could see the base was designed to act as a suction cup on walls or floors. She sat back on a sofa and had me squat, lube myself with two fingers for a few minutes, and then lower myself on to it. Not letting me stop until my buttocks touched the floor, and the entire cock was up inside my rectum. She had me lean back, balancing myself with one hand behind me, to allow her an unobstructed view. Then, with the other hand I was to masturbate, whilst I fucked myself on the cock.

"Don't waste an inch, there's a good boy, right to the top so you can feel the head about to slip about your ass, then right back down to the floor," she instructed.

When she was happy with my 'show', she told me not to stop, then without saying anything else stood and for the second time that day slid her knickers to the floor. This time she was facing me, and as she sat back down on the sofa, bottom on the edge, feet up and knees bent, I was afforded a perfect view of what to this day is the most perfect vulva I have ever seen. She grinned, knowing I was unable to look away, and proceeded to masturbate for me as she'd said she would. In silence, other than moans, and the soft squelching of the cock sliding rhythmically in and out of my asshole, we watched each other masturbate, until she came noisily.

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