I’ve been talking with Archer for a year or so. He is a straight boy very interested in becoming a sub. He had subbed for a number of professional mistresses – and really enjoyed it – but was wondering if he would enjoy being worked over by a guy.
He had come over once before for a bdsm session but decided – right after he put my cock in his mouth – that he wasn’t ready for it. We ended the session, he dressed and left but we continued to talk online occasionally.
A few months ago he started to suck the cock of another guy and found he really enjoyed it. He particularly liked making another guy blow his load. We talked and it became clear that he had changed his thinking and that he was more interested in hanging out and sucking cock rather than a strict BDSM experience. Mates hanging out having brojobs. We agreed to catch up to hang out and for him to suck me off.
Six five or so and dark haired. Piercing blue eyes. In a crisp blue shirt with white cuffs. Matching tie and socks. The socks with a matching band of blue that no one would ever see while he was dressed – but he’s taken the time to coordinate because it is important to him. Very masculine in a meticulously well organised fashion. He’s definitely a final year private school boy ten years on. He has that slight arrogance that many confident private school boys have. A carefully scruffy beard that is deliberately designed to soften his chiseled looks. Clearly a former sportsman of some talent and ability. Now a stockbroker who is paid to make snap judgements without second guessing himself.
We chatted and drank – he selected whiskey on the rocks – and discussed life and sex. It was really pleasant and I enjoyed our chat. After a half an hour it was time to play. We undressed and stood chest to chest playing with each others cocks. It was really reminiscent of being a school boy again. Feeling his cock and the warmth of his body against mine – before he suddenly dropped to his knees and devoured my cock. I was expecting him to be more of a beginner – and to look at, touch or lick it – rather than just cram it into his mouth. After some frenzied sucking I dropped into a tub chair and he knelt before me to continue his oral worship.
I began to slowly take control of his sucking – directing his head and pace. I pushed my foreskin forward and pushed it into his mouth. I commanded him to bite it which he did hesitantly. I ordered him to bite it with increasing intensity until he reached the pressure that I enjoy. He learned quickly to stroke my cock while licking my balls – and to vary the intensity of his efforts. It was really nice to see the dynamic changing from him grabbing my cock and taking the initiative towards me having control over him.
I led him to the bedroom and we rolled around the bed as he blew me. I pulled up his foreskin and chewed on it with reasonable intensive and his reaction indicated he finally understood what I was trying to teach him. I pushed my cock back into his face and his skills went up a notch.
I dragged him to the edge of his bed so he was on his back and his head was hanging over the side. I slid my thick cock into his mouth and started to fuck his mouth in earnest. Leaning forward I was able to suck his cock as I did – and politely pin his hands down so he was unable to prevent my cock from sliding between my lips. I fucked his mouth.
He’s got a great cock for beginner – a really small head but a shaft that lengthens out to a really thick base. Perfect for fucking a beginner twink – he can sneak the head in and then really open up his ass. I hope to do some threeways with him and some younger guys.
We sucked in a 69 on our sides, then with him in a doggy position over me, and lots of other combinations and permutations.
I reached down and grabbed a bottle of amyl from next to the bed. “Have you ever tried it?” I asked. He shook his head – but curiously rather than with rejection. I opened the bottle, wiped the top, and took a sniff and held it out to him. He copied me and inhaled. No reaction for about five seconds and I pushed his head down onto my cock. He started to suck and the amyl slowly kicked in. He pulled off my cock as the amyl hit its peak and breathed heavily as it made a impact on his system as only a first time user can experience.
Archer was now pretty anxious to get fucked. Particularly when I put him on his back, got between his legs and mock fucked him with my cock between his ass cheeks. We headed for the shower where I soaped him up and got him clean. He shivered as my liquid soap covered fingers rubbed up and down his ass. Normally I like to spend a bit of time in the shower but Archer quickly rinsed off indicating he wanted to be fucked now.
We towel dried and headed to the bedroom. On the bed I spread his legs and inspected his ass….and flicked it with my tongue. I could already tell this was going to be a tight ass. I flipped him around and rimmed his ass in a few positions.
I clipped the sling into place – connecting it with the stainless steel rings hanging from my roof. At the base of the sling I wrapped his arms around his neck and lifted him off the ground. Holding him in mid air i ran my fingers around his ass to tease him and went to lower him into the sling – which didn’t work. I’ve done this a hundred times but Archer was nearly two meters tall and with his arms around my neck he wasn’t high enough to be lifted in. I lowered him into the sling and he lay back himself. First time I’ve failed at that….and it’s a signature move of mine!
I got his arms and legs into position and gloved up. Cold lube ran down his ass as I slowly opened him up. I slowly worked a finger into his ass – which continued to grip tightly. His reaction to my finger massaging his prostate was pretty intense.
I got him to four fingers and I knew it was as loose as it was going to get. While this virgin ass had never experienced cock it has been fucked by a mistress wearing a strap on – one that I hoped was at least as thick as my rod, although that seemed doubtful.
I stripped off my laxex gloves and rolled an extra large condom down on my cock. With the lack of sleep the night before and the drinks I had consumed I wasn’t totally rock hard but it didn’t mater. I rubbed my cock up and down his ass and got some photos of it next to the cherry it was about to pop.
For about five minutes I was gripping my cock by the base so I remained hard as I slowly tried to ease it into his virgin ass. And then finally the head popped in – and was immediately pushed out. I now knew it was going to happen – Archer was not leaving this sling a anal virgin.
My cock head again slipped into his ass and was again pushed out. I repeated this pattern – until finally I pushed in deeper. As I slowly pushed the rest of my thick shlong into his tight ass his vice like grip acted like a cock ring and my cock became rock hard. I gave him a second to adjust before I slowly started to fuck him in and out. His cherry was now definitely a memory and yet so unused to to the sensations was the boy in the sling that he wasn’t sure it was in.
At this point I needed to start reassuring him that he was no longer a virgin – I was definitely balls deep in his ass. He managed to simultaneously look shocked, contented, proud, horny and in mild pain.
I picked up the pace and actually started him fucking really hard. After ten minutes of solid fucking he requested a break.
“Was I good?” He asked anxiously. I reassured him in no uncertain terms that he was – even though he continued to look uncertain.
We rested and he cleaned up before we decided to try again with him on his hands and knees.
As I started to push into his ass again he winced and I knew his ass was closed for business for the evening. I got him to lie down but his body language had become defensive. He may not have cum but I sensed his mind had definitely called game over for the proceedings.
He’s clearly a very analytical process driven person. You could practically hear the cogs in his head whirring as he tried to reconcile his experience with his life. He dressed and left, with neither of us having blown a load, with an extremely pensive look on his face.
I’m really looking forward to fucking Archer again. He’s always going to be a straight boy at heart – but I’m pretty sure I can turn him into a guy who also loves the sensation of lying back in a sling and taking a pounding. He really sucks cock very well.