0 comments/ 34351 views/ 0 favorites A Boy's First Time By: yourslavegirl He and I had been best friends since senior year of high school. I'd had a crush on him since we'd met then, and still had it even after he came out to me. Since we were both in college, we couldn't see each other as often as we would have liked to, but we got together as often as possible during winter and summer breaks. One winter break, about a week after New Years, we decided to go out together. We went to the mall to go shopping and see a movie. We had a really great time. As always, we talked about anything and everything. As anyone can tell, this of course meant talking about sex. The conversation didn't actually pick up until we were in his car and he was driving me home. Now, I love to tell people about my sexual exploits. I usually can't do this with guys, because more often than not, they get too horny. This time, however, I figured it wouldn't be a problem, seeing as how I'm not exactly his type. I mean, a girl just doesn't expect to turn on a guy who only gets turned on by guys! I couldn't have been more wrong. As I told my stories of the different guys I had given head too, he stopped me. "What is it?" I asked. "I'm really turned on right now," he admitted. I was completely shocked. I didn't expect to have any effect on him at all, yet he reacted the same way most guys do. "I kind of want you to give me a blow job," he muttered. I didn't know how to react. It was a total shock to me that he would even suggest it, considering that I'm a girl. But at the same time, I couldn't deny my excitement. Here was a guy I'd liked for more than four years and he was coming on to me. I told him that I couldn't, that it would hurt our friendship, but I was hoping he would do something to convince me otherwise. As it turned out, all it took was him telling me about his raging hard-on. We were on an extremely deserted back road at the time, so he pulled over to the side of the road and cut the headlights. It was so dark in the car I couldn't see him even though he was less than I foot away. I heard the sound of him un-buckling his seat belt and sliding the drivers seat all the way back. I un-buckled my seat belt and stretched across the seat. I found the fly of his jeans in the dark, and promptly had it undone. I reached into his pants and gently removed his stiff cock from its prison. I could feel it throbbing in my hands, and wet my lips in anticipation. I slowly lowered my head and took him into my warm wet mouth. He let out a deep groan as I swirled my tongue around the head of his wonderful cock. I ran my tongue over every inch of him, tasting him, expressing my love for him with each stoke of my tongue. I started to move my head up and down over his cock, and he thrust his hips to meet my mouth. I wanted to make him cum so badly, I wanted to taste his sperm, I wanted him to fuck my mouth so hard my eyes were tearing. Suddenly his hands were on the back of my head and he was forcing me down on his cock. His thrusts grew more forceful, and I nearly gagged as he fucked my throat. I kept my tongue moving over his shaft the whole time, still tasting him, still savoring him. I wanted him to use me, to make me his forever. I wanted to be his bitch, his plaything, his toy. For him to use however he pleased. He gave one final deep thrust, and let out a low groan. I felt his cock pulse in my mouth as he came. I savored his taste as I continued to gently suck his softening member. I sat up and kissed him gently on the mouth. Then I moved back over to the passenger's seat and clipped my seat belt. I heard him do the same. "I think you already know this," he whispered, "But you're mine now." He turned on the car and started back in the direction of his house. "I know," I told him, "I always have been." A Boy's First Time 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. ---------------------------------------------- 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. A Boy's First Time I never knew his name, but he knew mine and he'll never forget. You never forget your first. As I looked up at him it was his hair that struck me. Short. Blond. Set with gel in a kind of wedge shape with the apex over his right eye. I'm not much for hairstyles, but his was quite striking and so it stuck. His eyes were blue, his lips were dry and he was chewing the bottom one, but it was obvious he had no idea about that. His cheeks were red and he was breathing hard. From time to time he fanned himself, but it wasn't warm in the room and neither was he. He was terrified. First times will do that to you. He looked young. He was young. Suddenly I found myself wondering if he might be under eighteen. I shook my head with a wry grin. Of course he was over eighteen, everyone in the building was over eighteen. Given what we were all here to do there was no way it could be otherwise. I was getting old, I thought. Even policewomen looked like schoolgirls to me these days. The woman with him looked down at me. He was obviously in her care. Some minutes previously she'd introduced us and explained why she'd brought him to me. To relieve him of this terrible burden. She saw my rueful shake of the head. "Is something wrong?" She'd asked. "Just thinking of how young some of these people look." I'd replied. "Yes." She'd said with a laugh, "They get younger every year it seems. Still, at least no one here is under eighteen." The boy finally laughed. "God yes. I remember my eighteenth birthday. Not for any specific reason. It just seemed the time to point out that it was, in fact, an event in my past." "Ah well", said his chaperone. "Laurel will be so pleased to hear that. Time to get on with the story though." The boy and I shared a look. "Careful with the fourth wall." I admonished. "Pot. Kettle." She replied. "Whatever. Get on with it." He was scared of hurting me which was sweet. The older woman by his side had picked me for this honour, but he was her boy. She was going to be giving the guidance, telling him what to do and how to do it. When to be firm and when to be gentle. I was there to be penetrated, by her, by him - Who was doing it really? It was her, taking what she needed from me, she was just using the boy to do it. And the boy was terrified. I was far from passive though. I encouraged him, I made a show of being eager for him. I'm no virgin after all. This kind of penetration is something I'm well used to, but I've never been anyone's first. He's scared he'll hurt me but I laugh at that idea. He's young. He has no idea how resilient we are. Yes, if he gets it wrong I may bleed a little, but the thing he's preparing to slide into me... Lets just say I'll be surprised if I feel much at all. I've taken bigger things than that inside my body. I grin at him. The boy's concern is touching, but he has no idea... For a moment he's ready to run away it seems. The woman with him smiles forgivingly at him. It's ok, she says. You don't have to if you don't want... "You do have to", I tell him. "Now? Later? Eventually you'll have to do this and this is what it will feel like, however long you wait." He knows I'm right. It's time. If I hadn't known, I'd never have guessed I was his first. He slides it into me smoothly and steadily and I was right, I hardly felt a thing. "Is it in yet?" I ask and we laugh together, the three of us. He doesn't look nervous now. His face is still red, but now he's excited, pleased with himself. He'll never be scared of this again, and no matter how many come after me, he'll never forget. First times are special like that. I lie back and flex my buttocks as they've told me to. I move around, flex my fingers and toes. The boy and the woman walk away. They have others to attend to. I look around me. About a dozen couches fill the hall, roughly half of them occupied, from time to time a name is called and another couch is filled. I see a young girl in leggings and a tartan skirt. Her severe black spectacles and vivid red lipstick take all my attention. Maybe the boy will see to her now. I know he'll be gentle... Soon it's over and I get up and walk to the far side of the hall. I sit down and accept the traditional cup of tea and biscuits, and that's it. We're done. I walk out of there, a pint of blood lighter. The boy has lost something harder to define... That's right, it was a blood donor session. What did you think I was talking about?