My One and Only Penthouse Letter

When I was a teenager, nothing turned me on more than reading the letters in Penthouse. I actually liked them more than the pictorials. But I never had a "Penthouse letter" in my youth. Instead, it happened in April 2009 when I was 46.

I had recently been lamenting to my best friend Mark that I'd probably never again be with a woman whose age began with a 2. It had probably been 15 years for me since I dated a woman in her twenties.

I met Chrissy on an admittedly sleazy hook-up site. I had a profile but I didn't have my 'parts' posted. I saw that Chrissy was Asian and 23 so I made a general silly long-shot flirtation at her. I honestly didn't expect any type of reply besides "Move on, you lech."

But she did reply and she was very sweet. She told me she was a grad student in Boston but she didn't say where or what she was studying. She was very mysterious and her profile picture was sort of fuzzy so I really didn't know what she looked like. She did tell me that she wasn't a "typical" Japanese girl in that she wasn't skinny--which was fine by me because I don't like skinny women.

We e-mailed off and on for about a week. In that time she e-mailed me two soft core (bra and panties) pictures but again I couldn't see her face because she was really concerned about her privacy. I'm a face guy but I really liked what I saw in those pictures, especially her boobs and hips.

Friday afternoon she e-mailed me to tell me she would be free that night after 7:30. I leapt at the chance. I suggested a diner in Watertown. She agreed.

Before I drove to pick her up something told me NOT to wear blue jeans. So I wore my tan LL Bean chinos, a blue dress shirt and my Ecco shoes.

Parked outside her residence hall in downtown Boston I saw a variety of students walk by and man did they look young. I felt like I should be on Dateline and was praying that she didn't look like these young girls.

Not to worry. When Chrissy came out to the car my toes curled. She was no young girl. She was sexy as hell. She was wearing a sheer black blouse with a short skirt and sexy white stockings. (I have to say as a man: stockings give me an instant erection.)

So Chrissy got in the car and I think we both felt the chemistry instantly. She passed for 30 and was way more mature than her age. She had great boobs and when I rested my hand on the center console she didn't jump when I 'accidentally' brushed my hand against her stockings.

We parked a block away from the diner. I actually saw a couple girl friends from town in the diner but rather than cringe ("Shit they know she's younger than me") I was even more proud to be with her. Besides, sexy has no age.

Chrissy loved her meal and we had a nice talk. It's weird but not one sexual word or double entendre was mentioned the whole night. She was just a pleasure to be with.

Besides, I told myself, "All I want is a kiss."

Half way back to the car I stopped walking. She said "What?" and I told her I wanted to kiss her so we kissed outside a church. It was very romantic. And she let me softly brush her breast with my left hand as we kissed.

She agreed to come back to my place but we decided to stop first for some dark chocolate. As we walked into a Stop N Shop, there were flowers on the right. "What's your favorite color?" I asked. "Red, of course." I was impressed. Many girls might have said "That's OK, I don't need any flowers" but she knew what she wanted. A dozen long stem red roses it is.

She came into the apartment and fell in love with my cat which was cool. She realized she was paying a lot of attention to my cat but I was OK with it. Then she turned around and we kissed. Then I stood her up and we really kissed. Playfully I said "Too bad you don't like kissing". She protested until she realized I was goofing on her.

Then I told her what I wanted. "I want to take you into my bedroom and kiss your breasts."

So we headed into the bedroom.

The first time I placed my mouth on her beautiful breast she practically had an orgasm. (Guys her age must not do foreplay, I guess.) Then I kissed her mouth again before alternating between each breast.

Next I slid my hand down her panties. I expected to feel some moistness but instead she was sopping wet and frothy. A woman can say anything she wants about a guy and how he is as a kisser but their pussies never lie. I was so proud for making her that wet.

I took her panties off and I dove between her legs with my tongue and fingers. I absolutely love going down on a woman and she was going insane.

She opted not to go down on me but I was fine with that. Instead she put her hand in her mouth and grabbed my hard cock. I expected the hand to be slightly wet but instead it felt soapy and wet. I had never felt anything so sexy before. After just five strokes I had to ask her to stop.

I had told her when we first lay on the bed that we wouldn't be having sex. "That is, unless you can change my mind, " I said.

"Oh, I'm not the kind of girl who changes a guy's mind."

She was selling herself short. I was almost blind with lust and my cock needed a release. I placed a condom on and here's where it got even sexier. Rather than wait for the standard missionary, she got up, turned her sexy butt towards me and had me enter her doggy style.

I came in about five thrusts but was able to continue the motion for a few more.

After I came she lay on top of me for about ten minutes as I stroked every inch of her body.

Never in my life did I think I was capable (or truthfully, deserving) of a 23 year old with a tight hot body. But guessing by her several orgasms and willingness to see me again—hopefully soon—I was selling myself very short.

It truly was my fantasy night come true.

[While I ended up seeing Chrissy two more times, the magic of that first night was never duplicated. No regrets. I am one lucky man!]