Mansex Again, 25 Years Later

I had a long-term relationship with a bi friend from my early teens to early twenties. Our relationship was a closeness, and even love, that went well beyond what some would call "youthful experimentation", or "follies." Mind you, I love women, and love my wife, but for 25 years, and through two marriages and three kids, the thought of that "giddy man sex feeling" has never been far from my mind. My current wife understands this, and we're open about our bisexuality, as she and her college roommate were lesbian lovers and she had several flings with a gay co-worker within the last few years. We're both also very anal erotic and she's more than willing to fulfill my "anal proclivities" with dildos, a strap-on, and some very big butt plugs and toys.

As I've gotten older, and felt that perhaps time was passing me by, the thoughts of regular sex with another man with whom I could form a special friendship and bond, became pervasive and I finally joined an online gay and bisexual dating community.

Forgive if this gets a bit long, but this is how I tend to relate my life experiences to others. Doing so is a bit of a catharsis to me and allows me to get things off my chest. I've never really been into, "Slam, bam, thank you ma'am...(or sir)," sex nor am I into stories that merely say, "We came, we fucked, we left..."

When I first joined the gay and bisexual dating site, I was excited, and even a bit alarmed, at the number of emails I got from "interested parties." I quickly learned that many of those who wrote weren't all they appeared to be. Many wrote of grandiose plans for meeting, but then would back out when I tried to arrange the details. Even though I had many photos posted on my profile, many freeloaders really only seemed interested in obtaining more photos as they could not view the photos in the "Paid Member Only" section of my profile. Unfortunately, this has been my experience on more than one sex related internet site.

Several months after joining, and after looking at his profile many times, I finally wrote to a member named Eric. I mentioned that I found him intriguing and that I thought we might be compatible. The information contained in his profile seemed to be tailor made for the kind of person for whom I was looking. He was a tall, fit, low circulation, married man, with limited same sex experience. We live about 45 miles from each other.

He wrote back saying that he had been looking at my profile for some time as well. We exchanged many emails, shared images with each other, and discussed details about our experiences. I was always very open and felt comfortable sharing details about my past sexual experiences, my work, and my family. Though he was a bit more secretive and openly paranoid about being "outed", he too opened up eventually and shared many details about his life. Over time, I felt I had gained a friend and not just a potential lover. He made it clear that his wife knew about his bisexual desires, was accepting, supporting, and even turned on by it, and that she might someday want to watch or even participate. He had only one previous experience wherein, while both were drunk in a spa, he had fellated a long-time friend who had not reciprocated in any way.

After a month or more of trying to arrange a "date", with work, family life, or other obligations getting in the way, the day finally came when we were both free and it was actually going to happen. Though excited and immensely turned on at the prospect, I found that I was far less nervous than I thought I would be. I was apprehensive, but not really nervous.

As my friend was reluctant to meet in his town, or mine, we made arrangements to meet in a coffee shop in a town about halfway between the two. It was mid-morning, and we both had researched hotels in the area and had determined that several offered "early check in" if we were still "interested" after meeting. While driving there, he called me on my cell phone and told me he was running a few minutes late and wanted to assure me he was not backing out. After his call, my mind started racing, my heart was pounding, and I found myself squirming in my seat and rubbing my genitals through my pants.

I arrived first, went inside to get a table, and ordered some coffee. After sitting there for a few minutes he came in. As we'd exchanged many photos, I recognized him immediately. He didn't see me at first and while he stood there glancing around I had the opportunity to check out his physique from afar. I'd dreamed of this moment for weeks and he was everything I expected, and more. We finally made eye contact and he walked over to the table. I stood up, said, "Hi," shook his hand, and he sat down. He immediately took a deep breath, let out a long sigh, looked at me and rolled his eyes. I knew then how nervous he was and oddly began to feel like the old pro and mentor.

He was six years younger than me, 41 at the time and I was 47. He was tall, handsome, fit, and I was bit surprised at how attracted I was to him. Like me, his hair was cut very short and he was clean-shaven. I found myself thinking about the other places where he was "clean-shaven" as we had discussed that we both shave our cock, balls and ass. As I looked at his face, marveling at how beautiful he was, I found myself feeling ...well...gay. What can I say, it's just a giddy feeling I get only with men and I know no other way to describe it.

We talked a bit, in low tones, with only vague references to why we were there. He ordered Cherry Pie and, as he ate it, joked that it was symbolic as was about to lose his... "Cherry". We had discussed that his ass was virgin, and he wanted me to take his "anal cherry." As you shall see, that's not how things worked out. We looked at each other, and nearly simultaneously, started to say, "Are you ready to do this." We then paid the bill and went out to our cars.

We had decided on a hotel beforehand and we both drove there in our own vehicles. I could tell I was excited since my pulse rate had quickened, and my breathing had become deep, but I still felt remarkably calm. He checked into the hotel, walked back to the cars, and we drove around the property to park near our room. We chatted outside for a few minutes and then both grabbed our overnight bags and went into the room.

We checked the room out and found it to be nothing fancy, but it was clean, and would suffice. Given my past, I had no qualms about kissing another man, and really wanted to kiss him, but he had mentioned in correspondence that he didn't know if he could handle that...yet.

I joked that I was really "painfully shy", but then took off my shoes, socks, pants, and shirt, and sat in the chair at the desk in just a blue and black "Undergear" French Cotton Contour thong. My excitement was obvious and there was a dark patch where pre-cum had soaked through my shorts. He laughingly said, "I can see that," and began to get undressed as well. He made a comment about how much he liked my body and I found myself blushing and, once again, having that giddy "gay" feeling. I was anxious to get started as we both had obligations later in the day and we didn't have much time. My cock was already hard and straining to get out of my shorts.

As he undressed, I opened my overnight bag and removed some of the contents. My bag was just one of the erotic "toy bags" that my wife and I keep in the house. I explained to him that I had brought it, rather than pack something else, as I knew it would contain anything we might need, or want. It contained several boxes of condoms, numerous tubes and bottles of lube, including some KY Warming Liquid. It also contained several dildos, butt plugs, and "probes". When I pulled out my "Exxtreme Goose", from the Big Sex Toy Store, his jaw dropped and he exclaimed, "Can you actually take that?" I told him yes, but that it took a lot of work, and a lot of lube. I didn't expect to use the toys our first time together, but we had them just in case.

I placed the lube, and condoms, on a nightstand near the bed and then brought several towels from the bathroom, put some on the nightstand, and several on the bed. One was stretched out flat in the middle of the bed.

We lay down next to each other, talked nervously a bit, and commented on each other's bodies. I still wanted to kiss him but was afraid of freaking him out. We then, tentatively, began to stroke each other's bodies, chests and nipples, eventually rubbing penises through underpants. As he was trembling, his hands shaking, and obviously extremely nervous, I was totally surprised when he suddenly sat up, moved his head down between my legs, stripped off my underwear, and began to suck my cock. It was as if he felt, "If don't do this now, I'm not going to," and he dove in for all he was worth. He was doing a wonderful job and it felt great. Almost immediately, he also wet a finger with saliva, slid it into my anus, and began to pump it in and out. My head was swimming in sensation. I just tossed my head back and reveled in it for few minutes.

Initially, because of the way he was lying, I was not in a position where I could get my mouth on his penis so I contented myself by rubbing and massaging his shaved ass, in and around his rectum, and stroking his cock and balls with my hand. He raised his head and said, "Wow. That feels so good. You've already done more than my old friend ever did." His penis did not immediately respond and remained mostly flaccid. He sat up and said, "Don't worry, it'll get harder. I'm just very nervous."

I moved so we were now basically in a sixty-nine position lying on our sides. I took a long look at his gorgeous shaved cock and balls. I then began to suck his cock and lick his balls, perineum, and around his anus. I swirled my tongue on and around his glans paying particular attention to the bottom side in and around his hole. His penis slowly began to respond and grow. As he became fully erect, I began to deep throat him and was amazed that I still, after so many years, could take a penis so deep into my throat. Meanwhile, I was further astonished that he, my alleged same-sex virgin, had begun to rim me and was driving his wet tongue deep into my ass.

At some point, I don't know how or when, he had gotten the KY Warming Liquid off the nightstand. He squirted copious amounts on my ass, and onto his fingers, and began to work first one, then two, and then I don't know how many fingers into my anus. I had a warm glow coming from my ass as he pumped it violently while sucking my cock. It felt deliriously good.

His cock continued to grow as I sucked him and his cock head became so engorged that is was smooth and glistening. I had noticed in pictures we had exchanged that, when erect, his cock head was substantially larger in diameter than the shaft. More so than any I had ever seen in the hundreds, maybe even thousands, of porn films I had seen. Now that I had it in my hand, and swelling in my mouth, this anatomical difference of that "mushroom head" seemed even more pronounced. I can't adequately describe this as it had to be seen to be believed. It made for a very pronounced ledge where his glans met the shaft of his cock. I spent considerable time licking that edge of his glans and sucking just the head of his cock in and out of my mouth so my lips made ample contact with that spot.

As I sucked him, tugging at his ass cheeks to drive him deeper into my throat, he sat up, got on his knees, moved toward the head of the bed, supported the back of my head with his hands, and began to fuck my mouth. While he was thrusting in and out, I had slid one, then two, fingers into his ass until he was basically sitting on my hand while he fucked my face. I began to get faint, sweet, tastes of his precum and knew he was getting close. I wanted him to cum in my mouth in the worst way but, when he said, "I want to fuck you. Do you want me to fuck you?" I couldn't resist.

This was not how it was supposed to happen. I was supposed to fuck him, taking his "anal cherry." But...., "The best laid plans..."...and I am extremely anally erotic. At that moment, my ass was so hungry, he could have fisted me.

I'm sure the desire showed on my face as he asked how I wanted to do it. Had he been willing to kiss another man, I probably would have wanted it missionary style so I could kiss him and look into his eyes while he fucked me. As I didn't think he'd kiss, without a word, I rolled onto my knees, stuck my ass in the air, and waited for him to take me. He rolled a condom onto his dick, put more lube into my ass with his fingers, and began to slide his cock into my ass. He was going very slowly, as if he thought he would hurt me. My ass was hungry, his tentativeness was a bit frustrating, and the anticipation was driving me nuts. I wanted him deep in me NOW. I reached back, cupped my hand on his ass cheek, and pulled him into me as I drove my asshole around his cock. He sighed and muttered something about how he'd, "Dreamed of this view," his entire life. I then pulled my ass off his cock, and shoved it back on, repeating this several times so I could feel that huge cock head sliding past my sphincter again and again. He then began to fuck me in earnest.

He grabbed my hips and would pull me back onto him as he thrust deep into my guts. After a while, I reached up, grabbed several pillows, stuck them under me so my chest and head was laying on them. I was half expecting a "reach around" and when it didn't come began to stroke myself. I was pushing back with each of his thrusts, and pulling away each time he pulled back, so I could feel him sliding past every inch of my fuck hole. Each time he bottomed out, as his thighs collided with my buns, that extra bulbous cock head of his would brutalize my prostate. He was grunting and groaning so much that it almost sounded like the contrived sounds on a porn movie but it was real. He was just that overwhelmed with the sensations.

I literally began to feel like I was having an out-of-body experience as my entire consciousness was focused on my ass and genitals and I became aware of nothing else. Slowly, inexorably, my orgasm began to well up from deep within me. From the time that I began to feel that immensely pleasurable, "it's inevitable" feeling, till the time I finally exploded, it seemed like an eternity. My orgasm seemed to last forever as I shot, over and over again. The largest volume of cum I have ever had filled my hand and spilled onto the towel we'd laid on the bed. Never much of a noisemaker during sex, I found myself screaming, "Fuck!! Oh fuck!" My asshole, pulsing and gripping his cock as I came, drove him over the edge and I could hear him groaning, almost growling, as he writhed and filled the condom buried deep in my ass. He collapsed on top of me repeatedly uttering, "Oh my god. Oh my god"

We were both frozen in position, my ass in the air, him laying over me with his cock buried deep within, while we gasped to catch our breath. We finally disengaged. He slid his cock out of me, and I sat up and turned to face him (avoiding the lake of cum on the towel). He pulled the condom off and, still wanting to taste his cum, I grabbed him, pulled him to me, and licked his cock clean savoring the taste of the ejaculate still oozing from his member and a bit of the tangy taste of my ass. We looked at each other, for a moment I almost thought we might kiss, but he turned away and went into the bathroom to clean up. I followed suit and we both washed up. As he stood at the sink, I came up behind him, pressed my body against him, and briefly nuzzled his neck. He seemed to enjoy this, but that's as close to his lips as he let me get.

We then sat in our underwear talking. While burying his face in his cupped hands, and shaking his head as if ashamed to admit it, he repeatedly exclaimed that it was the best sex he ever had. We both wanted to do it again, but knew we didn't have time. I apologized for not "taking his cherry," as we had planned, and he said, "Don't worry about it. That was great. That was the best sex I ever had. You can fuck my ass next time." I was ecstatic at the thought that there would be a "next time." After a bit of mostly non-sexual chitchat, we finished tidying up the room, gathered our stuff, and headed for our cars. With a wave, he was gone.

As I drove home, my ass, still dripping with lube, tingling, and emanating a warm glow, felt great. I was drained, relaxed, and content. All I could think about was, "The next time."........ But, there wasn't, and never would be, a next time with him.

Over the next several weeks, we continued to correspond by email, chat, and phone calls, anxiously making plans for that "next time." I really felt I'd found another friend and lover akin to my friend from school. We even talked about an overnighter, maybe in Las Vegas, in a room with a spa. He seemed like it couldn't happen soon enough. Then suddenly, out of the blue, all contact ceased. He didn't respond to emails. He didn't respond to messages on the bisexual dating site. He didn't log into Chat or Messenger services that we'd used. He didn't answer his cell phone. He didn't even log into his bisexual website account for two weeks. When he finally logged in, he deleted most of the information on his profile, all of the pictures, and changed the description to read only: "I am no longer interested in playing." The next day, his profile was deleted entirely.

I didn't know what to think. I was half concerned, half angry, and totally upset. All kinds of wild thoughts went through my head. I finally sent emails to several of his accounts. I explained that I understood if he decided he didn't want to play anymore, as everyone has the right to make their own decisions concerning their sexuality, especially an alternate sexuality. I also expressed concern that some sort of family issue had arisen (perhaps because of me). I alluded to my concern that I had even feared that he had a health issue even, heaven forbid, an STD (even though we'd used a condom for our anal play). Ultimately, I said that I at least deserved a goodbye, and whatever explanation he might be willing to offer. He finally wrote back, and offered only that he and his wife had found that his having relations with another man had affected them both more profoundly than they thought it would. It seems that he found that his feelings for another man were more profound than he ever thought possible. It scared him...and his wife became jealous. I don't know, but in light of his previous concerns, I expect that he also became paranoid about being outed.

In any event, it hurt, but what we had, just that one day, was great and every bit of what I remember sex was like with my old friend so many years ago....and then some. It also confirmed, in my heart and my soul, that I can't go years and years without a man's touch. So, once again, I am looking for friend, playmate, and lover.