Lila Claire

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."

I was so nervous by now. I had to make sure that I smelled fresh so I showered and applied liberal doses of cologne in place that I don't usually use it. I was worried about performance anxiety and the last thing that I did before I left my room was to break out the little blue pills and swallowed one.

"Fuck it! I thought to myself. "I have to be a stud tonight." I took a second one.

When I stepped out of the cab at her hotel, Lila was already waiting under the portico. She hugged me and told me that I was going to be a gentleman and buy her dinner. This was New Orleans, so of course we ended up in an oyster bar. I was careful not to drink too much and made sure that I ate a light meal. I kept thinking how ridiculous I must look with a woman more than young enough to be my daughter but lust has an amazing power to overcome embarrassment. Lila's foot sliding up and down my leg and her toes on my cock under the tablecloth worked wonders too. I don't remember the conversation. I think that I was probably a total dork and talked about my kids and grandchildren and her job. She was gracious and endured my blather until the waiter came back with my approved credit card slip. She took it from him and gave him a huge tip. The expense lady deducted it from my check the next week and sent me an email asking me just how pretty my waitress had been.

We walked the couple of blocks back to the hotel. I was so incredibly awkward I don't think I said three words but then, in the elevator, she pressed up against me and kissed me. When we broke the kiss she told me that I was sweet and that I was going to have a really great evening.

I had sort of planned how I would make love to Lila. I was going to be slow and to touch every inch of her body, kissing down to her pussy and licking it the way I loved to do before I finally mounted her and made sweet slow love to her. Apparently this was not in her plans.

As soon as we got in the door she pushed me down on the bed and began unbuckling my pants. She pulled them down to my knees with my boxers and grabbed hold of my cock. Thank God for Viagra. I immediately got a hardon reminiscent of my teen years. Lila reached under her skirt and pulled off her panties then climbed on top of me and slid down onto my erection.

"Fuck me with that beautiful cock!" she gasped. "Give it to me!" She slammed herself up and down impaling herself on my chemically enhanced erection. I reached around her and held on to her ass cheeks, pulling them apart and moving my fingers towards the center where my cock was plunging into her wetness. I rubbed her juices on my finger and pulled her cheeks further apart.

"Oh my god, Yes!" she moaned and I pushed my wet finger into her tight little ass. I knew what she loves. It didn't take long for her to go over the edge. As she orgasmed, I felt her ass pulsing around my finger and heard her crying out in her passion.

The problem with Viagra is that it gets you hard but it has a really hard time letting you cum. Lila had two orgasms riding me and I wasn't even close. She rolled off of me to take a break and asked why I hadn't cum in her. I told her about the pills, both of them and she laughed.

"This could be a long night. It's a good job that I brought in reinforcements."

I didn't understand but she leaned over to the bedside table, picked up the phone and dialed a number. "You can come up now, "she spoke into the mouthpiece.

I wanted her to tell me what was going on but she just told me that she had promised me the night of my life and so far, it had been for her. Within a minute there was a tap on the door and Lila got up to open it. A very handsome young man in a pilot's uniform, about her age stepped in.

"This is Jim," Lila said. "I know that you know who he is."

I did. How could I not know? He had been in too many of our role plays.

"I think" said Lila in her huskiest, sexiest voice, "That we should all get naked."

Both she and I were still almost fully dressed. I helped her out of her dress and underwear while Jim hung his uniform on a hanger in the closet and took off his shirt. "Isn't he gorgeous?" said Lila. He was a very good-looking young man with a buff body that he obviously was taking better care of than I had mine at that age. I had not exercised between high school and my fortieth birthday and although I wasn't too bad, I certainly didn't have a body to match Jim's.

Jim faced us and took off his underwear. His cock hung down and it was long. I mean really long. Lila had her hand on my persistent erection, slowly stroking it.

"Jack," she ordered. "Make him hard. Let me see you suck him. It's okay. Do it for me. Do it for you too."

Jim crossed the room and stood by the bed. Lila moved over and motioned him to lie down. He did so and lay on his back with his legs apart.

"Give me your hand," whispered Lila, "I'll help you."

She took my hand and with hers over it I sat on the edge of the bed and together we reached between Jim's legs, took a hold of his long penis and began to stroke. I felt it harden in my hand and loved the feeling. I pressed harder and stroked a little faster. Jim's cock grew and grew and my hand, no longer needing Lila's help or encouragement, slid up and down the hard shaft. Jim's eyes were on my hand stroking him. I looked over at Lila. She was lying on the bed on her side, one knee raised, stroking her wet pussy.

"You know what you want to do, don't you Jack?"

My mouth was dry with nervous excitement as I moved to kneel between Jim's legs and then I bent over and took the head of his cock into my mouth. I licked his salty precum from the tip. I had tasted my own and found it both palatable and arousing but tasting this other man's was something else. I supported myself on one elbow. With the other hand I spread my saliva over his shaft as I stroked while my head moved up and down and my tongue massaged his thick cock. I heard his breath become ragged and he moaned a little. That is how I knew I was doing it right. Now I understood the old Seinfeld joke about being familiar with the equipment. I could imagine exactly what he was feeling form my own experiences.

Actually, I could feel most of what he was feeling because Lila was now behind me. I could feel her hot vagina pressing against my ass cheeks and she had reached around and was stroking me as I sucked and stroked Jim.

She rubbed her sex against me. I could feel the heat and the wetness flowing from her. I thought about the glass dildo and wished that we had it there so we could actually act out or last cyber fantasy. All of a sudden, my ass ached to be touched. Lila must have sensed that. She licked her fingers and began to rub one wet fingertip around my ass. Instinctively, I spread my legs wider and pushed my buttocks into the air. Lila's finger began to probe and she slowly slid it into me while I sucked Jim and she stroked my cock, finger-fucking my ass and rubbing her own swollen clitoris. Now it was my turn to moan as Lila's slender long finger moved around inside me.

By now Jim's hips were bucking up and down and it was obvious that he was close to cumming. He looked up at Lila as if seeking permission. "Let me see it!" she whimpered. "Cum in Jack"s mouth."

She attacked her pussy with even greater vigor. Jim let out a loud moan and I felt his cock twitch as his semen pumped through it. I opened my mouth for some reason and it shot against my tongue and dripped out the sides of my mouth. He must have been saving it up because he shot out three big bursts of jism. I moved to wipe it from my face but Lila grabbed my hand pulled my head around dragging me into a deep kiss. We shared Jim's juices and I felt her hand pressed against the side of my thigh and her fingers moving wildly. With our mouths locked together, she began to cum, her screaming muffled as her whole body shook and shook.

We all collapsed on the bed but I had still not had an orgasm and was numbly hard. I was regretting the second Viagra. Lila went down on me. Jim went down on me. I could not cum but even if I could I wanted this night to continue.

As Jim sucked on my cock, Lila lay back against the headboard and watched us. Her legs were open and she was slowly teasing and massaging her clit. I pulled out of Jim's mouth and moved between her legs, knelt down and began to lick and suck on her sweet pussy. She gave a little sigh and put her hand on the back of my head pulling me in closer and rocking her hips as her arousal began to build once again. Jim crawled up the bed and knelt to one side of her. His cock was getting hard again and he fed it into Lila's mouth. I didn't have a great view from my position but when I looked up, I could see that long cock stiffening and growing as she sucked it. I loved seeing it moving in and out of her soft mouth with her full lips that were swollen both from her arousal and from having sucked both of our cocks.

I licked and sucked and drank Lila's juices and watched as Jim pulled out of her mouth and came behind me. I was kneeling with my ass in the air and my head down between Lila's legs. Jim slid his long penis along my ass. The feel of it on my anus was delicious and I pushed it up higher. Lila was panting by now but she managed to tell Jim that there was lube in the drawer. He moved away briefly and then I felt his hands on my ass as he rubbed the cold lubricant on it. He moved back in and resumed his motion. I felt the underside of his dick sliding between my cheeks and then felt his balls bounce against mine. I could feel how hard he was.

He pulled back again and then I felt the head of his cock pressing against my virgin ass, slippery with lube. He pushed harder and the head began to open me up. I felt his cock slowly enter me, stretching my sphincter muscles and felt pain as he slid even further in. Now he was definitely inside me. He stopped and gently rocked, asked me if I was okay, to which I made a muffled "Uhuh" as my face was buried in Lila's crotch. The pain had subsided as I knew it would and I wanted more. I pushed back and he got the message and inched deeper into me.

I had suspected that it would feel different from the hard glass toy that I was used to using and I was correct. Even though Jim was fully erect, his penis had a give to it. Maybe a rubber toy would feel the same. All I knew was that it felt amazing to be fucked by a real cock in my ass after all of these years. As he slowly slid in and out of me, I felt the pressure on my prostate and I moaned in pleasure.

Lila was very aroused but not out of control.

"I want to see it," she said and she pulled out from under me, kneeling next to me.