Seduced with My First M2m Iss

I would go on a gay chatline looking for crossdressers and femboys who enjoyed dressing up in sexy outfits and having fun behind closed doors. That was the upper limit of my walk on the wild side and I was convinced it would remain so indefinitely.

Then one Saturday afternoon while I was on the chatline an older man sent me a chat request. I was 48 years old and he was 65 years old, the age I am now as I write this. I graciously accepted his chat request even though his profile did not match my interests. He was a nice gentleman and asked me what I was hoping to find online. I told him that I was looking for t-girls and crossdressers only, I'm pretty sure I stressed the "only" part.

He asked me if i had ever been with a "real" man and I assured him that I hadn't and had no desire to do so in the future. He continued to press the case why I should graduate to being with a "real" man since I had already been with men in female attire.

I told him that I was drawn to the best of both worlds, the beauty of the feminine form and the cock, passion, and desires of the male form. I had been with beautiful and sexy females but the most beautiful, sexy, and passionate lovers that I had been with were t-girls.

This back and forth went on for a while until I thought I had finally convinced him in my lack of interest and desire for a sexual encounter with him or any "real" man as he would say. A week later he sent me another chat request and I accepted it again. Even though he was not a good match for me I did enjoy our conversation.

He said he had been thinking about me and our chat and came to the conclusion that I had "pussyboy" potential. His reasons for coming to that conclusion were during our previous chat I had confided in him that I had topped t-girls, bottomed for them, sucked them, been sucked by them, and kissed them. And that what I enjoyed most was sucking t-girl cock, getting fucked by t-girl cock, and making out with them.

Of course I protested and told him I had never even thought about kissing a man, sucking a man, or being fucked by a man. He just chuckled and said he wanted to leave me with something to think about until we chat again. Then he said that he wanted me to think about the possibility that I was "hiding my desires for cock and men behind a pair of panties." I agreed to think about it and he said goodbye.

I did think about it and my initial reaction was "he wishes" but he's wrong. There was the time when I was with a beautiful CD and after making love for a couple of hours I jumped in the shower to clean up. She stripped off her lingerie and asked me if she could join me in the shower. I told her to come on in and she took off her wig and climbed in.

There I was naked in the shower with a cute, smooth man and I was horny for him but I justified it in my mind that he had just been my beautiful and sexy t-girl lover 15 minutes ago. So that was my extent of being with a male not in panties. I was still convinced that I didn't have pussyboy potential and that I wasn't hiding my desires for men and their cocks behind a pair of panties.

Like a moth to the flame, I somehow happened to be online the following Saturday afternnon at the same time we had chatted in the past. Like clockwork, or in hindsight cockwork, he sent a chat request a few minutes after I logged on. I eagerly accepted so I could once and for all convince him that he was wrong about my pussyboy potential and hidden desires for men and their cocks.

Before I could say anything he said that he was just online to check messages and noticed that I was online. He said he didn't have time to chat because he had already told his wife he was going to the gym and was about to leave his house. He then suggested that instead of going to the gym that he could meet me at the local hot tubs and we'd have an hour to chat.

I had been there quite a few times before, but always with t-girls or femboys who would dress up for me. I did have a collection of lingerie, panties, hose, gloves, collars, heels and wigs to give them the look I desired.

But this was the first time that I would be there with a "real" man. I agreed to meet him figuring that at worst I would spend a relaxing hour with a man whose conversation I enjoyed and at most I might thank him for his friendship and for paying the hourly fee by letting him give me a hanjob, or if I get carried away let him give me a blow job. But I was pretty sure that wasn't going to happen. As I drove to the hot tubs I questioned why I had changed from my boxer shorts into my black thong, the very thong I wore to try to turn on an ex-gf and all she could say was that I looked gay in it. Was I trying to tease him or send him mixed messages, or was my brain and body sending me mixed messages.

Thirty minutes later I nervously walked into the hot tub lobby and see an older man who smiles upon my glance. He walked to the counter and paid the fee and got the keys to our room that is equipped with a shower, jacuzzi, sauna, and a bed. I felt a little uncomfortable that the front desk staff knew I was going to the room with a man but thought to myself that at least they assume I am the Alpha male in the couple. As we walked down the hallway to our room he sensed my nervousness and told me not to worry, we will go at my speed.

My speed? My speed is 0 mph or maybe reverse. Did he get the idea that I was here to explore? I was there to explain to him that he was wrong.

We got to our room and he locked the door behind me and dims the lights. He says it's nice to finally meet you and gives me a hug. I thought that was a nice gesture and gave him a quick squeeze in return. As he pulled back from our hug he gave me a light kiss on my lips. Before I could react he surprised me by pushing his tongue into my mouth. Then I surprised myself by accepting his tongue and kissing him right back. My knees went weak but my cock got hard.

My mind was racing, I was kissing a "real" man, it felt so natural, it felt so naughty, it felt so gay, and it felt so incredibly wonderful. It was like a release and a relief. We continued to kiss as we undressed each other and then he led me by hand to the bed where we kissed passionately and intimately as we held and groped each other like long lost lovers. Now I knew what my speed was, zero to gay in one kiss.

He then guided me down to his 7.5" cock and I immediately fell in love with my first man cock. I had sucked many t-girl cocks before, but this time it was different. In the past, when I was between my lover's legs with their cock in my mouth, I would look across a smooth sexy body and see a beautiful girl's face enjoying my work. This time I looked across a hairy chest to see my first "real" man with a big "I told you so" smile on his face as I did my best to please him and his delicious cock.

From my time with t-girls, I had come to love sucking cock and really loved tasting and swallowing their cum. However many of the t-girls were either on female hormones or ejaculated so often that they didn't produce a lot of cum. I was really looking forward to getting a big mouthful of his manjuice when he interrupted my time in heaven and pulled me up for more of his kisses.

I climbed on top of him and almost enjoyed having his tongue in my mouth as much as I enjoyed having his cock in my mouth. He then rolled over on top of me and slid down and sucked on my modest 5" cock. I was rock hard from kissing him and sucking him before his lips even touched my cock. I was amazed at how he seemed to know exactly what turned me on as he expertly engulfed my cock and drove me to new heights of pleasure with his tongue and touch. But that didn't last as long as I had hoped as he stopped sucking and gave me a wet kiss with the taste of my precum.

I wasn't sure where he would lead me next but I sure was happy kissing him and sucking his big Daddy cock. He then reached for his bag and grabbed a tube of lube and went back to sucking my cock as he slid a lubed finger inside me, and then a second finger. That's when I realized he had bigger plans than giving a bj while he finger banged his new conquest/discovery.

I had been topped by a few t-girls in the past but none of them were hung like him and although I was looking forward to getting fucked, I wasn't looking forward to the initial pain I was about to experience. As I laid there with my legs spread in anticipation he lubed up his cock and looked at me and said "let's see about your pussyboy potential."

The words were barely out of his mouth when the head of his cock began sliding into my manpussy. I was quite surpirised at the low level of pain I was feeling, maybe his thick fingers loosened me up or maybe my mind and body were finally ready to accept having a cock inside me. It wasn't long before all 7.5" were inside me and the pain had transitioned to pure pleasure.

He then bent down and kissed me again which sent waves of pleasure through my body. Maybe it was my pussyboy potential becoming a reality because having a man's cock in my ass and his tongue in my mouth was the best feeling ever. I wanted him to kiss me and make love to me forever, it was amazing how wonderful it felt.

Just as I was revelling in being made love to, he pulled his cock out and told me that he was done making love to me. Before I could protest and beg for more, he said "Now I'm going to fuck my pussyboy" and the he rolled me over on all fours and entered me from behind.

When he fucked me missionary style, I truly felt like he was making passionate love to me with his cock and his kisses. When he fucked me from behind, I felt like he was using me and my body for his own pleasure, and I loved it! He grabbed my hips, pounded away at me with his hard cock, and spanked my ass in rhythym with his balls slapping against my balls. I wished that I could also kiss him at the same time but surprisingly it gave me great pleasure mentally as well as physically to have him use my body.

Just like in the Franki Valli song, as I recall it ended much too soon. A few powerful thrusts later he came inside me and collapsed on top of me. He was still inside me as he laid on top of me kissing my neck and telling me that I was his new favorite pussyboy which I would have taken as an insult 30 minutes earlier, but now it was the ultimate compliment.

After a few minutes of pillow talk while he continued to kiss me and wiggle his cock inside me, he pulled out, slapped my ass, kissed me on the head, stuck his cock in my mouth for a quick clean up, and climbed into the jacuzzi. I was lying there wondering if this were a dream or a wonderful reality. Did that really all just happen? Less than an hour ago I walked in there convinced my bisexual side hit its peak at being with beautiful t-girls, and here I was face down on the bed with the taste of cum in my mouth and my "real" man's sperm swimming inside me.

And all I could think of at the moment was that I wanted more of his cock and more of his kisses so I climbed into the jacuzzi and sat on his lap facing him so I could get more man kisses. I felt like the luckiest schoolgirl who had just been fucked by the biggest stud on campus as I kissed him passionately and lustfully as I wiggled my cum-filled ass on his cock.

He sat on the edge of the tub and I took my place between his legs and starting sucking on his semi-hard cock. I may have been floating in the water with his cock in my mouth as my anchor, but I felt more like I was floating in the air becuase having his cock in my mouth was my new heaven.

The room phone rang way too soon indicating that our hour was up in 10 minutes. I spent a few last glorious minutes with his cock in my mouth and got one last taste of his precum to send me home with a delicious memory.

We showered together so he could go home as if he had just worked out at the gym, I knew he enjoyed our workout a lot more. As he walked me to my car I thanked him profusely for recognizing and releasing my gay side and for revealing my gay role to be that of a man's pussyboy.

His surprise kiss just an hour ago revealed a new side of me that I didn't know existed, and I would be forever grateful for his perception and boldness to kiss me. It was still daylight as we said our goodbyes and using discretion he shook my hand, and then I surprised him by pulling him close and giving him a wet kiss goodbye.

As I drove home I thought about what he had so insightfully said, that I was hiding my desires for men and cock behind a pair of panties. Maybe all it took was a kiss from the right man at the right time to open my mind, and mouth and legs, to be with a man. Perhaps t-girls were my gatweay, a stepping stone, to being with a "real" man.

All I can say is that I am very grateful for my introduction to the pleasures of m2m sex and passion. I still adore t-girls, but there is something very special about being with a man and submitting to a man and the next time a man tries to kiss me I am definitely going to let him. And you should too!