Lana: First Encounter

Author: Ken Johnson
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Krissy’s Note: I really love autobiographical stories like this one that Ken Johnson sent me. I think there is something really, really erotic about remembering a favorite encounter and then writing about it and putting it down on paper for others to enjoy. I can definitely relate to some parts of this story… from the girl’s perspective of course! I can’t wait for the Second Encounter!

Well, I occasionally surf Craigslist in the Casual Encounters section clicking on the t4m button. More often than not I see the regular posts. No one over 35, big cock, muscular a +, face pic a must, no cock pic, 420 friendly, you must host, etc, etc. I wonder, ‘what are these people thinking?. Is there actually a boatload of people out there surfing who are willing to share a face pic and meet all the other requirements?’ Hmm. All I know is that I am in my 50s, relatively fit, normal sized equipment, a nice guy and clean but cannot host due to my personal situation and am only available occasionally during the day and some evenings. A tough set of parameters but what the heck – I keep looking.

Just before Halloween I am browsing and come across a post – Asian, 29, nearly passable CD looking for older Caucasian male, interested to play, bottom only, maybe a Halloween date. I decide to check it out even though I realize the likelihood of being free on Halloween is low. On the other hand, maybe I can make the connection and meet at another time. I like Asian t-gurls and although I have been with transsexuals, nearly passable CDs do turn me on. I can’t imagine being with a guy but somehow the girly look, the sexy underwear and the garter with sheer nylons does it for me. So I reply without much optimism ‘Hello: Older caucasian gentleman here who enjoys asian tg gurls. I am 6′, 185 lb, fit and not bad on the eyes. I hope to be out and around this Saturday. It would be fun to meet. I am well educated, professional, play safe but would enjoy treating you like a lady and then enjoying a sensuous erotic time in bed. Also, I’d be interested to meet other times if that interests you. xo Ken’.

Well what a surprise. I get an answer.

‘Hi Ken, got your message (obviously!) & you sound like someone I’d want to meet. What part of town are you at? As in my ad, I will be driving around to many places on Sat. night. It would be great to meet up somehow. I will be starting from my Lynburg then going into downtown some time. I will be on the computer here for another hour and one half. Lana.’

So after multiple e-mails we were set up to meet on Halloween. Since her cell phone was a work phone she didn’t want me to call her on it. Also, I discovered that she didn’t have a computer at home so communication was tied to her visits to the local library to check her e-mails. So no real time communication – not good. Our first meeting time planned for Halloween was a bit loose. Anyway, it never came together – I had e-mailed her in the afternoon and she was never able to get back to me so it never happened. I thought, probably this was just another flakey CL connection.

I decided to e-mail her again to say I was disappointed that it hadn’t worked out but maybe we could come up with another time. Perhaps a waste of time but one never knows. A quick e-mail wouldn’t take much time and perhaps the mix-up on Halloween was unavoidable. On the other hand, maybe this was just another flakey CL connection. It was a shame though as Halloween is the perfect day for being out and around with a CD. I thought opportunity lost but her e-mails seemed sincere so perhaps it was worth one more try. Of course, I had still not seen a picture nor had I shared mine so there was that uncertainty as well. ‘Nearly passable’ could mean lots of different things.

So I in a day or two, I received a response….

‘Hi Ken, Sorry about Saturday. I didn’t know how to get a hold of you without a computer & there was no time to get to one. It (Halloween) was very mellow for me as it turned out. Too swamped & tired to want to do anything in the end. Anyway, I don’t live full-time as a tv so I am limited as to when & where to meet (that’s why Halloween would have been good). Would it be possible for you to come to my place one of these days? See if we hit it off or not? I like no pressure. If you somehow don’t feel a connection with me or vice versa, we could just say, “Nice meeting you & best of luck.” How does that sound? Lana’

No regular computer access, no phone that I could call. This is going to be tricky. On the other hand, a nice invitation. No pressure. Check out the chemistry and go from there. So I followed up. Several days and multiple e-mails later we had arranged a date. I had a free evening as did she and I was to go to her apartment at 7:30 pm just to meet and see where things go. I had agreed to bring a nice bottle of pinot grigio – I enjoy relaxing with a glass of wine and it seemed that she was up for that as well. Things were looking good.

During the multiple e-mails she had confessed to her nervousness about the whole thing particularly given that she didn’t know much about me other than from my initial response to her post. I had told her a bit about me – professional guy, straight acting, easy going and more about my physical appearance and sexual preferences. It seemed as though we were a pretty good fit. Her job made meeting somewhat difficult although she confessed to a willingness to take a sick day to meet if we hit it off. I had learned that she was quite tall, had natural long hair (a big plus+ for me as I just can’t get excited about wigs), no boobs (actually kind of a turn on for me) and smooth. She said she loved to suck and enjoyed mutual oral, liked to kiss and caress and wasn’t sure about anal as she had not had a lot of experience and was tight. She said she was almost passable in the evening but lived as a guy and was not effeminate. She did say she had been dressing for a long time.

So the day arrived and as usual I was a bit nervous. I found myself in kind of a daze as I drove to her apartment hoping that things would work out and looking forward to a relaxing sex filled evening. We had talked on the phone once to set up the evening and she had a very feminine voice but I could tell that it was her ‘tv’ voice, something she had perfected over time. So I knew this was not some passing fancy of a guy experimenting with a CD experience.

I found the address. A clean looking 3 story condominium property, not fancy but OK, a property occupied by hard working immigrant families, most of them Asian. I found parking in the street (two hours). I ring the buzzer and, at the same time, feel a reaction in my groin. Somehow, my brain has signaled to my c**k where I am and where I am about to be. Maybe it knows something I don’t. Anyway, I go with the flow.

I head to the elevator thankful that there is no-one else in the reception area or entering or exiting the building the same time as me. Why that would worry me I don’t know. But somehow, I am more comfortable without others around. Who knows, maybe someone will recognize me and ask what I am doing in this neighborhood. There is nothing wrong with the neighborhood, it is just somewhere I don’t normally go. This is a private part of my life and I don’t need anyone else to know, just me and my new friend.

I find the apartment and tap at the door thinking that I do not want to generate any unnecessary attention from any neighbors and assuming that my new friend probably feels the same way. I hear the deadbolt being turned and the door opens slightly, my new friend is behind the door so I have no idea yet what she looks like. I enter and she steps out from behind the door. With heels, she is my height. Cool, I think, I like tall and she has natural black hair (almost big hair, but straight) falling below her shoulders. I like that too. She is wearing a halter style shoulderless black evening gown which stops above the knees, black sheer nylons and high heels. Her shoulders are a man’s shoulders although only because I know she is a man. She could as easily be a woman and have an athletic swimmer’s build. In a one piece Speedo swimming suit I am thinking she would look just fine. Maybe a little bulge but… I like that.

She welcomes me with a little peck on the cheek. I respond and seek out her lips and give her a brief kiss. I fuss with the wine after she finds the corkscrew and she hunts down some glasses. The apartment is sparsely furnished but comfortable and there is straight porn playing on the flat screen TV. I am not that excited about the straight porn – a beautiful blonde giving head – but it does get me thinking. There is a couch with a coffee table in front. She brings the glasses and I pour some wine. ‘Cheers!’ I say and take a larger than normal sip. I am still nervous and I can feel the wine warm my throat and I begin to relax….

We make small talk for a while. She works for a small accounting firm and is divorced. I explain that I have my own business, am separated. We have similar interests and we talk a bit about our history. She had her first experience with a guy as a teenager in a shared room on a trip and coincidently had been dressing discreetly at home for years. Her interest had never been discovered and she ended up marrying thinking that it was the thing to do. It hadn’t worked out, even though she viewed herself as ‘bi’, things never panned out. She was much happier on her own but actually seeking out a male companion who would meet her as a transvestite was something new. The CL post that I had seen was her first venture out into the world of ‘Casual Encounters’. She wanted a regular thing and had no interest in multiple partners. As well, it was clear that she had two lives, one as a straight accountant and the other as the attractive sexy transvestite sitting beside me.

I had to admit that I was a CL ‘Casual Encounters’ junky – although, there were seldom ‘women’ that posted that interested me or were interested in me. ‘35 and under’ seemed to be the big stumbling block for me. In the back of my mind I kept thinking that if they would only spend some time with an older guy they would come to appreciate the patience and life experience they typically offered. Realistically, I wanted a regular arrangement as well. It was just hard to find the right person.

After a while I was reminded of one of the reasons I was at her apartment. Although relaxed chatter was great, there was periodic stirring in my groin. She was sexy and I was eager to explore and find out more about the woman beside me. I leaned in for a kiss and next thing I knew our tongues were locked together and darting about one another’s throats. We embraced, paused, pulled back and started again. Wow, how long I had waited for this experience – a great kisser, a seemingly genuine honest real person who just happened to be a CD, and a hot, sexy one at that.

Another sip of wine and a bit more chatter. And another long embrace and kiss. I felt her hand work its way down to my pants and seek out my hardening c**k. Ahhh. She knew what she wanted because after feeling me she sought out my belt buckle and zipper. Next thing I knew her hand was caressing my c**k, moving up and down, exploring, gently but firmly. Hmmm. What more could I ask for… Soon I was hard and we continued our embrace and wild kisses as she played with me. I thought I should do a little exploring myself but I was enjoying being taken care of and Lana seemed totally happy and engrossed in her activities.

Before long she was pulling at the waist of my pants and boxers. She wanted them off, or at least out of the way. Before I knew it they were around my ankles. I didn’t even bother to slip them off as I was lost in the enjoyment of being seduced by my hot companion deeply engaged in the eroticism of the moment. Next thing I knew, her lips found me and I became even more lost in the moment. I thought – this is too good to be true. And even better, soon I was completely down her throat. She had done this before and was good at it. Then she was no longer beside me on the couch but kneeling on the floor in front of me giving me 100% of her attention. Her eyes looked up at me with all of me down her throat. Her tongue worked my c**k as she looked into my eyes. Alternately, she swallowed my c**k then pulled back and kissed and bathed its length with her lips and tongue. I could tell she was happy. She continued and I thought about pacing myself. We had a bottle of wine to drink and the better part of an evening to enjoy plus the last thing I wanted to do was to cum too soon revealing an inability to control myself and sustain the enjoyment of the encounter. After a while she dropped down, exploring my balls with her lips and tongue which drove me crazy. I was leaning back with my feet in the air – my clothes now somewhere on the floor – enjoying every minute of the attention I was receiving.

The wine beckoned. Probably a good thing to take a pause. We chatted some more and I told her how much I was enjoying our first meeting. After another glass of wine my curiosity overwhelmed me. I reached under her gown and worked my way up her leg, feeling the garter straps and eventually finding the edge of her black satin panties. My exploration confirmed what I already knew. She was a CD and there was a c**k. It was very hard and, to my surprise, very big. She had to have a 7 or 8” c**k and it was thick. I was in heaven but I thought about my 6 inches and felt a bit inadequate. I didn’t comment on her size but eventually she let me know that size was not important to her. In fact, due to her lack of experience with fucking, she was more than happy with my average size. She had gagged a bit earlier so unless it was an act, any more would have been wasted. I liked her size but was relieved that I had made it clear that I wasn’t versatile. Deep throating was one thing but having that in me was something I couldn’t imagine.

I asked her to stand while I remained seated on the couch. Then I was staring straight at her c**k pointed at the ceiling but pushing out the front of the black satin panties. One of the things that drives me wild is a hard c**k, its shape visible inside sheer panties. With two fingers, I pulled the panties aside and her c**k sprang free. Could I manage to get it down my throat? I started slowly and eventually my lips where at the end of her shaft. I couldn’t stay there long but I was able to show her my appreciation for the fine treatment I had just received. And I was enjoying the reciprocation. She was hard and clearly enjoying my efforts. As I leaned in she whimpered and sighed and occasionally thrust her c**k deep into my mouth gently holding the back of my head.

After a while she said ‘my turn’. ‘Face fuck me.’ I stood as she kneeled on the carpet. I had now removed my shirt and my c**k was throbbing. I grabbed it briefly and felt the hardness and the ridges of veins engorged with blood. I held it as I moved toward her and she sucked me in deeply. I placed my hands on the back of her head and began to thrust in and out. I could tell she loved it. I paused and she wanted more. After a while I pulled out and stepped forward so that my balls were draped over her mouth. She licked them and worked backwards to my prostate area. This was driving my out of my mind. I had never had such an erotic experience before. I could barely control myself.

Time for another glass of wine. We chatted some more, both sharing how much we were turned on and enjoying one another. After a while, I settled down. She was lying on the floor. I pulled her panties down and over her heels. I couldn’t keep myself from taking her in my mouth again. This time I was opposite her but facing the other way and soon her lips found my c**k and we were locked in a ’69 with me on top. I paused and leaned forward as she worked my shaft, then sucked my balls and the sensitive inner part of my thighs. We ravished one another for several minutes. It seemed like we had been making love for hours.

Finally, during a pause she said ‘I want you to cum in my mouth. What do you want?’ I could barely contain myself. I was so hot and ready to erupt but at the same time I wanted to prolong the ecstasy that I was feeling. She took me deep in her mouth and grabbed my butt, one hand on each cheek. She pulled me toward her and I began to thrust in and out as she pulled and let go. For some reason I thought about the word synchronicity. This was it. Except these weren’t unrelated events. Here were two people totally engaged with one another experiencing pure erotic joy. I came with intensity I could not believe. She swallowed everything and I could tell by her smile that she was as happy as I was.

To be continued….

The Author welcomes your comments at:
69kenjohn at gmail dot com