I don't know how you did it to me. I must have chatted and had cybersex with a hundred women but only you got me to tell you about my best friend in high school. It was my proto-bi experience. I told you in the chat room how we would play strip Poker and then jack each other off. I can still remember the feel of his cock in my hand. It was a little shorter than mine but had a huge mushroom head that I would run my hand over, spreading his hot-precum around and then stroking his rock hard shaft until he shot cum all over. It seems like we had constant erections in those days, often at the most inopportune times. What I wouldn't give to be that fast to jump to attention now. Those erections only come around with the help of a little blue pill now that I'm in my late fifties.
I'm not saying that we were innocent or naïve but we had never heard of oral sex back then. Kids are so much better informed these days. If either of us had, I'm sure that we would have taken turns sucking one another off. Sometimes I would think back and wish I had done it and imagine sucking a stiff cock. What if we had known about anal? Would we have fucked each other's tight little teenage asses? We lost touch after high school when I left for college on the west coast. I cannot find him even through old mutual friends on Facebook. I wonder if he grew up to be gay.
Talking about asses, mine remained cherry until I met a woman online who loved anal and who had a boyfriend who loved to be fucked with a strapon. She persuaded me to play with mine and so, in my forties, learned to enjoy the feel of my wife's well lubricated hairbrush handle in my ass while I stroked myself off. I even got her to play with me a couple of times and we discovered that she really got off on anal sex. Who would have thought?
But it was all a secret until I met Lila. Lila Claire, younger than my own daughter but having something...what was it? How was she able to draw out my secrets so easily? How did she get me to tell her how much I loved stroking S's cock? How did she get me to tell her that I wished, I mean really wished that I had known more back then; that we had experimented further; that I really regret that I never sucked a hard cock? I know I could have sneaked off and done it but I don't find men attractive at all. All that hair and hard muscle doesn't do it for me. Give me a toned woman's body any day. My wife is still damn hot but a guy's mind still thinks about other bodies. Mostly I think about firm young women full of lust with wet juicy pussies but sometimes I think about my games with S and wonder what it would feel like to suck another man's cock or even to be fucked by it.
I met Lila Clair in a chat room. She was 26 at the time a speech teacher at a Catholic school in Louisiana. Maybe she had some sort of bayou witchcraft thing going but there was an instant chemistry that I have never had from a chat room. It wasn't just the chemistry either. The cybersex was so real. I could almost feel her body and I would cum so hard from our chats. She broke down my barriers. I downloaded Messenger onto my laptop so we could voice chat. She has the voice of an erotic angel with a touch of huskiness that drove me wild. When she orgasmed, something she could do frequently and repeatedly, she was unbelievably vocal. She was unbelievable.
I think that it was only our second or third time of chatting when she got me to tell her about S. I think that our topic may have been how she loved anal stimulation and that is how we got to go there. She couldn't believe we only stroked. How could she at her age? She grew up with porn everywhere and Bill Clinton getting blowjobs in the Oval Office. She wanted to know if I had to do it all over again, would I have sucked him. How could I lie to her? She wanted to know my deepest secrets and I couldn't not tell them to her. She wanted to know how much I liked to have my ass played with and I told her the truth about the hairbrush. As I did, she fucked her pussy and ass with her vibrators and came to a breathless orgasm while she looked at the picture of my hard cock that I had sent to her.
She loved my anus and she loved making me play with it and put whatever was handy in it. She loved telling me how, when I visited her, she would invite her handsome pilot friend and make me suck his cock as she sucked mine and I fucked her. For my 55th birthday she made me go to a local sex shop and buy myself a toy and some lube. Then I raced home to get online with her and she listened to me as I fucked myself with the little dildo vibrating against my prostate to a screaming orgasm. It was me doing the screaming. Truth be told, I wished I had bought a bigger one and I told her so. Of course, that is what she got me to do. I went online and bought a long, slender, double-ended, beautiful glass dildo that really is a piece of art, with deep blue swirls and nubs. My wife still thinks that it is hers.
Lila and I had a date to play with my new toy as soon as it arrived. I had told her that my company had just issued me with a new laptop and as soon as we connected with Messenger she told me that she knew it must have come with a camera and that I had to turn it on. I cannot say no to this enchantress. All it took was one click and I was naked in front of her showing off the toy and ready to use it on myself. I still cannot believe that I lay on our bed and fucked myself deep and hard with the crystal dick or that I turned over and told her that I wished it was a real cock in my ass. She came to a shuddering orgasm when I told her that I wanted her to get on top of me and fuck herself with the other end of the dildo. Then she talked me into my own by describing how her friend Jim would fuck me and shoot his hot cum deep in my ass.
But there is another side to Lila. Like many women with a huge sexual appetite, she also had a fiery temper and more than once got mad and hung up on me. Then I would hang around the chat room, sometimes for a couple of weeks before her own horniness brought her back, seeking me out. It was always over something that seemed trivial to me. The first time it happened, I used the C-word. She hated that word and you can be sure I never used it to her again. She must have had some kind of Catholic guilt too because a couple of times she would berate me for being a dirty old man, chatting with young women about their rape fantasies (something else she hated) and for cheating on my wife in cyber. I actually agreed with her about that and if I had not been so addicted to her would have quit chatting before I actually did.
So it turned out that the glass dildo on camera was the last time we played. I think that she was offended because she had sent me an email right afterwards and I had never replied. In fact, it only showed up in my inbox months later. Maybe that was something that was just supposed to be. Anyway, I retired from the chatting game. I was finally realizing that I was sort of pathetic, the kind of guy that I would make fun of and, if it were not for my company needing me to work on a project in Louisiana, I am sure that the story would have ended here.
When I found out that I needed to spend a work week in New Orleans I couldn't help but think about Lila. I have never met anyone from online and I have never touched another woman in the flesh in the three and a half decades of my marriage. But this was Lila Claire, the sorceress from the Bayou and before I left for the trip, I found myself reviving my secret e-mail and telling her my schedule. I didn't hear anything back from her for almost a week, something that both disappointed and relieved me. But then, the day before I was due to leave, I checked the email and there was her name in my inbox.
"If you dare to leave Louisiana without fucking me, I will hunt you down and cut off your delicious cock!" That was it. Oh, that and her cell phone number.
The first day, I had a 6:00 am flight and worked with my rep until after 8:00 pm. I staggered to my room and barely had the energy to undress before I fell asleep.
The next day, I called her from the hotel. She had parent-teacher meetings for the next two nights. We had not talked yet. She told me by text.
That only left Thursday night. We texted and set up our date. She actually said that she was taking the afternoon off work and would drive down to NO and would be in a hotel in the French Quarter. I had the hardest time working that day. I had a major presentation to make to our client and I have no idea how I got through it. My rep wanted to take me to dinner but I refused, telling him that I needed to get my reports done for the week. When he dropped me off at my hotel, I pulled out my phone to call Lila and my hands were shaking.
She told me to get into a cab and get my ass downtown in a hurry. Of course I obeyed. You know the effect she has on me. She promised me that this would be a night that I would never forget. I laughed and asked her if it was going to be a good or a bad memory. She put a little extra husky in her voice and a little extra southern and said, "Honey, you're going to have the night of your life. And so am I."
