Deflowering A Gay Virgin

I love milking gay virgins and making them climax for the first time. They trust me because I have a reputation for being patient and gentle.


I don’t know exactly how it happened, but somehow I earned myself a reputation as the neighborhood deflowerer of young, curious boys. I don’t think I did anything to earn such a title, but an old queen like me was hardly going to complain, now was I? Being in my mid-thirties at the time, I was, of course, not ancient, but considering the median age of the gay community in my part of town, I felt I had to go pretty far away from home to find someone my age. Not that I often had the urge to go cruising for ass my own age anyway, with all the sweet young meat coming my way, but I guess everybody needs some experienced hands once in a while.

Anyway, I got lucky a few times at my local gay hangout and got to take home a few lovely, young virgins. I couldn’t believe my luck. Then somehow word had got around that I was gentle and gave the new ones a hell of a first time. I never considered myself a miracle worker in bed, but I loved virgins – as probably anyone else would – and was blessed with patience and self control. On top of that, I just loved seeing those shy young guys becoming little wildcats as I slowly worked them to climax in my bed.

So there I was. Richard, an average gay man with no stunning looks or manners, being treated to all the young meat I could stand. It’s a time I remember with the greatest of pleasure, now, later in life. There were many young men worth remembering in those days, but one in particular I still remember with a little flutter in my loins.

It was a lazy Saturday as any other when I got a call from David; one of my previous deflowerings and now close friend. He had turned into quite a little horn dog and had sent newbies my way before. Needless to say I was flattered and gladly accepted the commendation. Anyway, he called to tell me that he had given another newbie my number. I was fine with this, of course. Although he warned me that this one might be a bit of a hard nut to crack, he was very certain that this guy was a diamond in the raw just needing some unwrapping. His words, not mine; he was never exactly poetic in his phrasing. But, in retrospect, it turned out to be very fitting.

Hardly three hours later, another young man called. He told me his name was Andrew and that he had gotten my number from a friend. He sounded like he was almost on the verge of tears and practically whispered into the phone when I asked him if he was ok. He told me he was just nervous, and after some more whispering and stuttering, we agreed he should come over that same night. I made sure he knew he was free to back out and that if he did show up, we would only do what he wanted to. His “see ya later” was whispered so low, I couldn’t even sure be he said anything at all.

I made my usual preparations for a cozy night in bed. I showered, shaved, lit candles in select places in the bedroom and wore my usual relaxation outfit; a pair of satin pajama pants and a knee-length satin robe closed loosely over it. Comfortable, easy to peel off, but not too scary for a nervous first-timer. And just in case he really was as nervous as he sounded, I made some coffee and waited for him in the kitchen, so as to start off with something completely non-sexual when he arrived.

And arrive he did, right at the agreed time. He was so nervous when I opened the door, I thought it amazing that he didn’t run for the hills when I asked him to come in. He was shaking and shivering like he was cold, but it was a warm summer night, so I didn’t think it likely. He looked young. Very young in fact, but I was sure David would never send me an underage guy. He wore pretty thick glasses but the eyes beneath them were brown and had a very deep expression. His lips were nicely curved with a blushing deep pink color against his lighter skin. He had short brownish-blonde hair and looked like puberty hadn’t really reached an end yet. He was pale, very thin and seemed a little clumsy in his movements. Despite his gangly figure, he had lovely narrow hips and a wonderful long neck that made my mouth water. He had no hint of facial hair but smooth skin with a few freckles. He was obviously shy, but I thought he looked absolutely delicious – glasses and all. What can I say, I’m a hound for young guys.

I invited him into the kitchen and offered him coffee. After some gentle nudging, I pulled out of him that he wasn’t much of a coffee drinker and pushed a soda into his hands. He seemed a little relieved to have something to do with his hands and clutched the bottle so hard his knuckles turned white. I was starting to think David might have misread this little cutie. He looked so fearful I was afraid I might do serious damage if I made a move. So I took it as slow as I possibly could. I talked to him about everything and anything, got very short and quiet answers and slowly his clenched up shoulders seemed to relax just a little bit. So I thought we might as well approach the true purpose of our meeting.

It took a little time. I stared intently at him, making him raise his eyes and meet my gaze. I smiled at him and immediately he blushed and looked down. God, he was adorable! When he finally looked up again, I asked him what he had tried. He looked like he had no clue what I was asking. So I clarified that I wanted to know how experienced he was. He locked his gaze on the floor again, and mumbled something about ‘one date with a girl’ and I think I heard the word ‘disaster’ in there somewhere. I thought I’d better cover the basics, so I asked him how long he had been interested in men, if at all. This time he never even lifted his eyes as I asked. I thought I saw his lips move, but no sound came out. This wouldn’t do. I reached over and hooked my forefinger under his chin and lifted his face up. His eyes were closed like he didn’t dare look at me. I held my grip, though, and after the longest time, he finally opened his eyes. I tried as gently as I could to coax an audible answer out of him, just holding his gaze. He wiggled a little, as if trying to escape my touch, but then sort of resigned himself to the situation and really talked to me.

“I… I think I’ve always been curious about guys. I only went out with the girl to try it.” He closed his eyes and winced. “It was horrible”.

I really felt we were getting somewhere now and pressed on a little, hoping he wouldn’t clam up on me again.

“So, you’ve never been with a guy before?”

This time he surprised me by looking me straight in the eye, with a little bitterness to his expression.

“Never even a kiss.”

I got the feeling it wasn’t for lack of trying, and I think I guessed now why David had sent him to me. He was absolutely lovely, but so tightly wound up he really needed some gentle guidance to start with. At this point I wasn’t as much turned on, as feeling protective of this handsome youth. I really wanted him to blossom and I couldn’t wait to be the one to set his body on fire. But all in good time. And we had plenty.

I thought it was now time to make a move, so I leaned over my small kitchen table and placed a little peck on his cheek. He immediately froze and looked back at the floor. It was adorable like hell and making my heart race, but I took it even slower, wanting him to find out the right way what he wanted. I placed my hands over his, as he still held them tightly around the soda bottle on the table. I could feel him shaking a little and just held my hands there until the shakes subsided. I thought now was the time to apply a little pressure. I had to be sure he would be able to say no if I pushed too far.

“Tell me what you want.”

No reaction.

“Please Andrew. Just talk to me. I won’t do anything if you don’t want me to. So please, tell me what you want.”

He was breathing hard now and was obviously gathering courage. He mumbled again, but realized that I probably hadn’t heard what he had said. So he swallowed hard and lifted his eyes to mine.

“I want… I want… you to kiss me.”

I thought it was a wonderful place to start and told him so. He blushed again and just waited for my move.

“I need you to promise me you’ll say no if I go too far.”

I looked intently at him until he answered quite clearly and very fast.

“I promise. Please kiss me.”

The last bit caught me slightly off-guard, but I smiled and got to work immediately.

I stood up and walked to his side of the table. I gently pulled him up to me and put my arms around him. Our height difference was such that my chin could rest perfectly on his head, and I just stood like that for a while, hugging him to me. His arms slowly snaked around my waist and just rested there. I then reached a hand behind his head and tickled the hairs on the back of the neck lightly, while slowly tilting his face up to mine. His eyes were closed, his mouth slightly open and his breathing shallow. I slowly – ever so slowly lowered my face to his and placed the softest kiss I could possible accomplish on his lips. He trembled. Very much. I asked if he was ok. He nodded, still with his eyes closed and his lips parted, and I felt his arms tighten slightly around my waist. I moved in to deepen the kiss and he parted his lips a fraction more to allow me access. I gently probed around his tongue for a while and finally felt him responding a little. I broke the kiss and just looked at him. His face was flushed and he was panting softly. His eyes were still closed behind the glasses. God, I was having trouble holding back now. He was so gorgeous and I just had to tell him. When I did his eyes flew open and he stared at me with obvious disbelief.

“You’re joking!”

He looked like he was about to cry. I thought I’d better make things crystal clear to him, so I pressed myself against him. If he didn’t notice my rock hard boner through my thin clothes, he would have to be extremely dim. There was no mistaking his reaction when he felt it against his belly. He gasped loudly and dug his nails into my hips. I felt his own member through his jeans against my leg and while I didn’t get the feeling he was packing anything big, there was no doubt about the state it was in. I thought it must be almost painful for him, as hard as it felt. I moved my face very close to his, so he felt my breath on his lips as I answered.

“I never lie about those things. And even if I tried, my boner would betray me right away, don’t you think?”

He just stared at me and stammered.

“I… I… I’m not… gorgeous.”

He breathed out the last word and tried to close the distance for another kiss, but I teased him and moved away a fraction. I had him now.

“Then what are you exactly?” I whispered and licked my lips, still just looking into his eyes.

He looked like he was about to faint on the spot and tried again to kiss me. But I held him from me waiting for an answer.

“I’m… I’m… I… dunno… “

I chose that moment to close the distance and bite down on his lower lip. I sucked it into my mouth, feeling the warm blood rush to it, and finally letting it go with a little wet noise. He gasped. I pressed him still tighter to me and growled into his ear:

“Tender… so young and tender.”

And then I bit down on his earlobe.

His knees buckled and he moaned loudly into my ear. He clung to me so hard I felt his nails digging sharply into my back and pressed his groin so tight to me that I’m sure it must have hurt him. Then I suddenly felt a wetness on my thigh. I looked down and had to smile in amazement when I saw a wet spot on the front of his jeans. He had obviously just come hard in his pants. He still clung to me and hid his face on my shoulder. Then I heard a sniffle and felt a little sob run through him. I forced him gently from my shoulder and looked down at him. What on earth was the matter? I bent down and kissed away the tear I could see running down his cheek. I was very afraid that I had pushed him too far after all, and I said I was very sorry if I had crossed his boundaries. This just made him cry harder. He clung to me again and sobbed something into my shoulder.

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3 thoughts on “Deflowering A Gay Virgin

  1. frank says:

    This was a very hot story. He was so kind to this younger man, even while he was tempted to overpower and rape him. The young man perhaps would have liked being raped. He sure did like being fucked and sucking and kissing and all of it. Like to hear more of this.

  2. skyreader47 says:

    A wonderful concept for a story. We older guys can’t help but envy our lucky deflowerer. And the writer delivers with a slow, well-paced journey into cherry taking. Our protagonist is always thoughtful and never predatory. He so wants young Andrew to savor this important moment in his life. Oh, it’s totally hot as well for readers.

  3. MH4848 says:

    Such an incredibly hot story! I’ve finally accepted my feelings after long denying them and what I wouldn’t give for a man like this to guide me like that-even though I’m not anywhere near as young and attractive as the kid in the story I feel deeply for him.

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