The first time my ass was penetrated was when my wife and I were having sex and she took the vibrating dildo I had been using on her and put it in between my ass cheeks as we were fucking missionary. We were both pretty wound up really enjoying ourselves. So much so I reached behind me and shoved that big dildo in my ass. I could feel it vibrate and bounce as I pumped into her. I think she could feel the vibrations resonate through my ass into my cock and she came wildly. That sent me over the edge and I came too. Many years later after menopause causing her to loose interest in sex and me not being done with it I had the desire to have a real cock in my ass. Well I haven’t been disappointed. It can feel very good, but yes it can hurt also. My ass is very tight. I have found that as part of my preparation if I clean out and use a butt plug before going to meet a guy I’ll already be loosened up enough to avoid it hurting. It makes it so much more enjoyable. Lots of lube will make a big difference also. Once the initial stretch of penetration has occurred and Im lubed up, I’m ready.
Yeah, my lady will ask, "You need some dick, huh?" which is my cue to find a guy and suck him off and to get sucked off...
Unless I found another gay or bi friend, my wife and her trusty Strapon will fill the bill and my ass.. She knows when I really need it. My only trusted friend won't be back until spring and in the meantime I have to whore myself out to my wife. It's rare, that she can read the signs of need, but when she does she knows how to take care of business.
I sucked my first cock when I was 16. I was working an after party with the city’s elite. You had to know someone who knew someone to get into the party. This was back in the mid/late eighties, before social media killed a hot sex scene in most cities. My boss was the host, he was openly gay and would make comments to all the male staff, usually, “last one done, has to blow me.” These after party’s started around 3am and went until they ended. I was in one of the rooms enjoying the company of a very happily married older woman when the door opened. I knew the voice instantly and thought “fuck-it, I’m getting fired. But I’m going to enjoy this pussy before I left. I was offered a choice, blow the boss or lose my job. The woman was all over this idea and wanted to watch. She even helped the boss undo his pants, pulling his cock out. She gave it kiss and beckoned me closer. Encouraging me all the way until the tip of his precum cock touched my lips. Between the woman and the boss I worked his cock, sucking and stroking up and down the shaft. Between the woman fondling my hard cock and the bosses cock in my mouth, I couldn’t tell you who exploded first. The woman was kind enough to lick my lips clean of the bosses cum. Years later, I’m married, we had a very active sex life. We were swingers and usually had a female third as a regular play partner. We had played with a few couples but the men were very vanilla. My wife was working overseas for a few months and I was invited to a party at a local pub by one of the ladies in the office. Arriving at the pub I was introduced to a couple. Throughout the night the woman talked about new and exciting things going on in her and husbands life. Being the curious guy I am I asked about the “new”. I was blown away when she said she had convinced her husband to suck cock for his first time. I was instantly hard with the thought of a virgin mouth around my cock. She explained the husband was picky about body shape and look and that they had been seeking a male third for many months. Paying the tab, I was invited back to their place. Drinks were served as the three of us lounged in the hot tub. She worked her way close to me, lifting my hips while simultaneously guiding her husbands mouth around my cock. For his first time, he was good! Holding my hips above the water both of them took their turns sucking my cock. We retired to the bedroom where the two males worked over the wife. He was a little hesitant when I went to touch his cock. His wife managed to get him on his back and she rode him slowly. Pulling herself off his cum soaked cock she guided me over. I took his cock into my mouth, tasting her pussy. She joined me in cleaning up his cock. He was tense and not very relaxed but watched me intently as I took his cock to the back of my throat. As he was about to cum, his wife took his cock in her mouth and swallowed his load. This went on for a few years. it was an amazing triad. My wife knew about my bisexuality but wasn’t keen on playing with two cocks, she was a pussy girl. Years into our marriage we rode motorcycles with a few bicouples. The rides usually ended at one of the homes of one of the couples. And while I enjoyed our sex life, I couldn’t wait for the next ride with our new friends. I wasn’t looking for any one-on-one time with any person in particular but knew it happened. On one ride it was late ending and we had stopped at a pub for some food and a drink. As I was leaving one of the riders grabbed me and kissed me. His tongue finding the back of my throat. I enjoyed the moment, letting the kiss linger longer than we both wanted (I think). My wife was like, WTF was that about. Told her I wasn’t sure because this guy and I hadn’t really played with each other. She was surprised by the kiss…
Have enjoyed a few occasions of trading oral but been quite a while. Penetration wise has been various toys including wife and her 6" strapon
I have so many stories I'll have to wait until I have my full keyboard in front of me. That said, kissing a man gets me hard immediately. YMMV.
Back in the good old days it was relatively easy to find an Adult Bookstore with video booths and even glory holes! Almost impossible in my area now. So many hot memories.
My first time with another guy was at my wife's suggestion. In our sex activities, it had gotten to the point where she used a dildo on me sometimes. When she saw how much I loved it, she said I need to try the real thing. I met a guy guy who fucked me and found out my wife was right as usual. I've had sex with 5 guys over the last decade but only with one for the last 2 years or so. I enjoy it when he cums in me, either in my mouth or ass. The feeling of his dick sliding in and out of my mouth is wonderful and the pulsing when he cums is awesome. I love the taste of the cum before I swallow. When he fucks my ass and his dick is rubbing against my prostate is almost enough to make me cum. I enjoy fucking him because I can stroke his dick while doing it. His blow jobs are better than my wife's because he's more enthusiastic about it. I have sex with my wife about twice a week and with my boyfriend, as my wife calls him, about once a week. Life is great.
Use to go by an adult book store and loved to watch and be watched. Gave and received a few hand jobs. Always wanted to give a blow job but to worried I may catch something.