I arrived outside his house at 7am the following morning and sat in the van for a moment, thinking about where things were at, like I had done most of the night. Here was guy who was starting to accept his interest in men, becoming more comfortable with looking at, touching and being touched by another man. I was flattered by his interest so far, but in the back of my mind was the fact that part of my role in this situation was to allow him to explore his sexuality without pressure, and I needed to make his exploration of. MM sex my first priority. The last thing I would want would be for him to lose interest, or worse, feel guilty or ashamed of his exploration as I intended this to be a really good experience for him. I wasn’t quite sure where he was at with MM sex as lots of the things I had introduced him to seemed to be new experiences for him, and it blew my mind that he had never seen precum before; still, I was in my mid thirties before my precum production became noticeable; ten years later I could literally soak my underwear if sufficiently stimulated. The other thing I couldn’t get my head around was his comment on Saturday about using the olive oil to lube his arsehole; he clearly had little knowledge of men at a sexual level and was shy about what he wanted, but was growing in confidence with MM sex activities. The comment about the olive oil suggested he had some knowledge of arse play and certainly responded well to my touching in this area. I wondered if he was in fact a MM virgin, and had been exploring his hole solo while developing an interest in men. I was sure I would find out as things progressed.
I saw him peek out the window while I was thinking, and a moment later he appeared at the van window. He was wearing a long-sleeved shirt and a pair of shorts; I noted that the shorts didn’t hide much of his excitement. My rugby shorts weren’t a whole lot different; there wasn’t a lot of material covering my balls and my cockhead was rapidly making its way upward under the waistband. He noticed that I noticed and I noticed that he noticed; we looked up at each other and our eyes met. I held my gaze and he stared at my cock again before I stepped down out of the van.
I gathered up my tools for the day, wondering quite why I was going through the motions- our MM sessions over the last few days had taken up quite some time and I hadn’t achieved much on Monday. However, I wasn’t really concerned as I had made good progress previously.
I wasn’t 100% sure what would happen when I went into his house, but something told me that at some point clothes would come off and we would end up engaging in some sort of MM sex activity, and probably on the kitchen bench since that seemed to have been a favourite of his so far. It was a good height, and wide enough so he could lie back with legs spread like he had done yesterday, when it was quite clear what he wanted me to focus on.
I closed the door behind me and followed him into the kitchen, where he offered me a coffee. I accepted and sat down while he made the coffee; I could see he was still aroused; while the coffee was brewing he pulled up a chair and sat opposite me; I could tell he wanted to say something but didn’t know how to. I sat silent for a moment before asking him what he wanted to say. He was silent for a moment, and then slowly told me that our session the previous day was something he had enjoyed like nothing else previously, and that he had fantasised about sex with men for a couple of years but never dared to act on his fantasies. I told him that I thought that may have been the case. I looked at him questioningly for a minute or two and he jumped up to deal with the coffee. While he was doing so, I asked him to tell me if he had ever played solo with his hole. He brought back the coffee and sat down; he was really quiet for a couple of minutes and wouldn’t look at me. He broke the silence by asking how I knew, and I told him why I thought he might have done so – that he was comfortable with me fingering his hole and the area around it, and his suggestion of olive oil as a lube for my fingering. He admitted that yes, he had played with his hole regularly and it was something he enjoyed so far; he had seen it on a porn video he had watched online and was fascinated enough to start exploring his hole with his fingers and with carrots.
I asked what it was about the feeling he liked, and he didn’t reply. He quietly admitted he felt guilty that he liked something in his hole. I thought about his admission for a minute before telling him about my FB who helped me to accept my interest in men. He looked up at me, clearly interested, and I asked him if he wanted me to help him like that. He quickly told me that I was already helping him in that way, and asked if I would be patient with him. I agreed and he leant down to kiss me; I could smell his slight musky cock smell while holding him close and it made me twitch while I undid his belt and fly. I saw why he was tenting his shorts earlier in the morning and rubbed his cock firmly through the thin fabric before releasing him from his boxer shorts and sucking his cock head into my mouth. He gasped and I took more of his cock into my mouth until I had taken almost all of it. He continued to gasp and babble as I slowly moved my head up and down; I was gagging while his cock was in my throat but managed to keep going. A moment later I was aware of the the pulsing of his cock as several shots of cum hit the back of my throat and I swallowed his load.
When he sat down, he seemed in a daze and I quietly asked him if he had enjoyed my attention. This time he didn’t turn red with embarrassment and directly told me that he loved it. I asked him what else he would like me to do and after a moment’s consideration he told me that he would love to continue yesterday’s rimming session. I agreed and sent him to the bathroom to freshen up; I quickly diverted him into the shower, where I instructed him on how to wash out to avoid an accident. When he came back he sat on the kitchen bench and quickly found a position with his legs in the air. I pulled up a chair and started by gently tonguing his exposed arsehole while holding his balls up; he moaned and squirmed and I repeated my tongue movements for a minute, before firmly but gently inserting a finger into his arsehole. He moaned again as I worked my finger inside; I continued, adding another finger and licking his hole beside my fingers. He was in heaven, moaning and squirming and the muscles around his hole pulsating. I asked him if he was ok and he asked me to continue gently. I established a rhythm with my fingers, pumping them into and out of his hole slowly and firmly as my cock continued to wet my stomach and shorts with precum; his cock remained hard and flat against his body.
I asked him what he thought of the rimming session so far and he eventually responded that he felt his hole could be fuller; it was clear to me that he was not comfortable communicating his desires. I asked him to tell me what he wanted, did he want me to bring a dildo for him to try? He hesitated for a moment before asking in a very shaky voice for my cock. I was surprised and asked him to tell me again what he wanted; he looked directly at me and quietly told me that he wanted my cock in him, and asked me to please be gentle.
I took a condom from the pocket of my shorts where I had placed them earlier in the morning and dropped my shorts and boxer before rolling the condom onto my sticky cock; I had some idea that they might be required this week but was a bit surprised it was today. I stepped out of my shorts and boxers and lubed my cock and his arsehole before placing my cockhead on his hole. I left it there for a moment before very slowly and gently applying pressure, all the time looking him in the eye.
My cock slowly disappeared inside him and I could feel it opening him out as I entered. He flinched a little but showed no other sign of pain; I continued to slowly push in until I was balls deep before asking him if he was OK. He nodded and mentioned he loved the feeling of being filled up. I slowly withdrew my cock and gently entered him again; on the third stroke he started to moan in pleasure and continued to do so the entire time I was inside him. His hole relaxed as I continued and he became easier to penetrate; it became obvious to me that I was opening his second hole as I penetrated deeply because I could feel pressure moving on and off my cockhead as I moved inside. I fucked him like this with his legs in the air for nearly 15 minutes until I was ready to cum; I was just about to ask him if he was ready when his cock shot several spurts up his chest, and the rapid clenching of his arsehole triggered my orgasm. I rapidly filled the condom and immediately held onto it while withdrawing it as it was very full: it was very slippery with his juices and mine. He lay on the bench for a moment before I helped him down and led him to his bedroom where I removed his shirt and mine, and laid him on the bed. We spooned and I became hard again; he reached back and held my sticky cock.
When he awoke, I made him a coffee and we sat at the kitchen table again. He seemed quite happy, as if some of his apprehension had lifted and I asked him how he found the MM sex experience. He was so embarrassed that I was so open about sex and I explained that shame and guilt would put one in a very dark place. He eventually looked me in the eye and told me that what we had done that day had been really good for him, and especially taking my cock. I asked if it was the first time he had taken a cock; he confirmed what I had suspected, that he was a MM sex virgin; he had been curious for a couple of years and had become used to fingering his arse and using carrots to satisfy his curiosity.
