Harriet, My Teacher

I'd known I wanted to have sex since I was 12. However, with me the gap between wanting and doing was about as wide as any adolescent could make it. Even through college my sole sexual experience was with my left hand. There were no girls at the men's college I went to, and at the mixers I never got much more than a sweet kiss. After graduation I got a job in New York City and was really on my own, with an apartment and some money, I decided that I had to start living.

I took an evening assertiveness training class and learned one major truth: it is easy to get where you want if you ask.

Harriet and I worked in the same ad agency, me in graphics, she in creative. While we weren't on the same end of the floor, we met occasionally in the lunch room. A couple of times we stood in line at the microwave and exchanged small talk.

At the weekly accounts meeting, my boss said he was shifting me to a message campaign.

"The account needs quick response, and that's your strength," he said. "It's going to be an evolving campaign, so you and the creative team will have to work quickly when the time comes. There's already a creative team in place. I want you to make this campaign sing!" He always talked that way but he was serious.

Harriet was the head of the creative team. She outlined the problem.

"The client wants subway ads, but what she needs is a print campaign. The budget is the same but media buying gets us more eyeballs for a lot less money in the free weeklies than in the subways, because they deliver the target more efficiently. So we can spend some of the budget on a rough-and-tumble PR person."

It took her almost two weeks to convince the client, but she came around. The PR guy got the client the free press that set up the print ads, and we had a winner.

The night we finished the last ad, everybody crashed and went home, except Harriet and me.

"Man, that was rough," she said. "Let's relax tonight. I'll buy dinner and you can do the movie." She knew that I was new to the city while she was a native. Since she had worked at the agency for three years to my eight months, she also knew I made less money. I was grateful, both for the attention and for the split.

The conversation at dinner wandered from business to my newness in New York. By the end of the meal she had volunteered to show me around the "real" New York, the neighborhoods, the jazz clubs, and the little theaters.

The next two Saturdays she wore me out going from museums to galleries to theatres. I learned the difference between the East Village and the West Village, the East Side and the West Side. She always made a point of ending the day with my buying us dinner at a small, inexpensive ethnic restaurant.

On the third Saturday we ended up in a Greek restaurant in her neighborhood. As we got up to leave, I asked her if I could go to her apartment. A soft expression came over her face and she said, "You're a nice guy and if I weren't gay I'd like to have a relationship with you."

I was stunned, both by her directness and by the concept of a woman homosexual, which was not something I'd even ever thought about.

"But we'll go there and talk."

She had a nice two-bedroom place in an expensive building. Plied by drambuie and kind but persistent probing, I unburdened myself about my life, a conversation I'd never had outside the walls of my head. Before long I was telling her everything about my not-so-interesting past and my yearning to start living, including having a relationship, love, and sex.

I finished up in a flourish.

"Since you like women," I said, "will you to teach me about how to attract and please a woman?"

"That's so sweet, but how I attract a woman and how a man attracts a woman are two very different things.

"But I like the idea of being your cicerone. It would be a real challenge. So many men are pigs about how they approach and treat women, gay or straight.

"How can I help?" she mused, out loud but to herself. She straightened herself on the couch and leaned back.

"My personal history may get in the way. When I was in college, I struggled about whether I was gay or not, I had sex with two guys. There was the thrill of the chase and the giving in, but ultimately I didn't find it fulfilling. Only with another woman have I really begin to know my body and find enjoyment in pleasuring and being pleasured."

"Look," I said, "consider me an act of charity if you want to, but I've got nowhere else to turn. I've gone to bars, attended college alumni mixers, wandered through the big museums looking like I cared. I appear needy, and I am, but I don't know what to do." This was the boldest I'd ever been.

"Let me think about it. Pencil me in for your place on Saturday after lunch. I'll let you know by Wednesday if I think I can do it."

She arrived around 2, armed with a shopping bag. She explained that she had thought a lot about what I needed to know and how she was going to teach me.

"Let's get started. Take off your clothes."

While this was the opening scene of one of my fantasies, it quickly dissolved as she made it clear that I was the only one getting naked. I stripped and she looked intently at me, walking in a circle around me.

"You don't take very good care of your presentation," she said. "You have a nice enough body but your pubic hair is overgrown, your pits are raggedy, and you need to keep your beard and head trimmed better. Also, change your underarm deodorant."

She took a bedsheet out of her bag, spread it on my bed, and brought out a pair of barber scissors and a comb.

"Lay down," she commanded. Harriet then proceeded to correct all the hair imperfections she had noticed. I got an erection, which she completely ignored, and it went away.

As she barbered me, she kept up a running commentary, telling me that a woman makes decisions about her companion from the beginning.

"No one's perfect, except in our ads, right? And we know how much trouble we go to airbrush out any imperfection. Your responsibility is to take advantage of what you have and package it in the most appealing way you can.

"Okay, now get dressed."

She checked out my closet and dismissed most everything in it except for my jeans.

"I've made a list of important characteristics and rated you honestly. Your conversational skills are good. Your posture is excellent. Your manners are excellent. Your work habits are good, though you keep a messy desk. But your self-confidence is weak.

"You can't have self-confidence if you don't have experience. From what you told me the other night, you have little experience with women and what you have had was pretty lame.

"Soooooo," she strung it out, "I'm going to assume that you need to start all over again, as though you are in junior high school.

"Which means learning how to kiss."

I had assumed that we would not be getting physical, but that turned out to be wrong. She sat down next to me on the bed and told me to kiss her the best way I knew how. I started out with a lip lock, sucking in. She said that was fine. Then she kissed me on the neck, flicked my ear lobe with her tongue, and returned to my lips and stuck her tongue in my mouth! I responded with my tongue and we tongue-wrestled.

"You're an okay kisser," she said. "Now I want you to undress me."

As my hands rushed to unbutton her work shirt and yank it out of her pants, she smacked me on the side of my head.

"No!" she said sharply. "You have to do everything slowly, lovingly. This isn't a race. By the time you're taking a woman's clothes off, you can be sure she's willing to have you. Here, I'll show you" and she reached over and started unbuttoning my shirt.

She started slowly, opening the top two buttons, then brushed her lips across my chest.

"Take every chance to make light, soft contact."

When she had all the buttons undone, she gently lowered my pants. She didn't stop there and took her time to finish undressing me, down to my briefs. Of course by then my erection was in full flower and I was shaking like a leaf in the wind.

"Finish me," she said. I bent down and removed her shoes and socks and started to stand up.

"Touch me slowly as you move around my body," she said, and pushed me back down. I put my hands lightly on her left leg and slowly moved up to her waist. Then I undid her jeans and let them drop to the floor.

"Lower my pants by yourself and kiss my legs as they go down," she said. "Take your time, a girl wants to be touched constantly. Do it again."

I pulled her jeans up, buttoned the top and rezipped them. Then I started again, taking the time to caress her ass, her belly, and her legs as I slid them down to the floor. I kissed her inner thighs as I stood up, slowly this time. I repeated the process with her panties. Then she slowly removed my briefs, absently touching my thighs.

After a glance to review the results of her barbering, she turned to her bag and brought out a pastel-colored cylinder.

"I like to have my lover use this. I'll show you how."

For the next two hours I learned how to move the dildo all over her, around her pussy, even into her. She brought out some oils and had me rub them all over her as I moved the dildo. I was erect for the first half hour but then lost it, since she offered no attention to me, just told me where to put the dildo and rub the oil, so that SHE felt good. I learned how to kiss and touch everything she had, front and back. She told me both times that she had an orgasm.

It was after six when she made her announcement.

"You're as far along as I can take you. You're going to be a great lover of women." I was exhausted.

I had gotten everything I had asked for and had no claim to anything more. But here I was naked with a woman to whom I had delivered a great deal of pleasure and she seemed indifferent to anything I might want.

I lay down next to her, hips to hips. She started to pull away but I grabbed her around the waist.

"I want you to teach me the only thing I don't know! I want to have a complete education."

"I never said I'd do that," she said flatly. "I told you, I tried it with guys five years ago and it didn't do anything for me."

"Well, how about something short of fucking? We can do oral sex." She inhaled deeply, then exhaled.

"All right."

Since we were both naked, and she had all that oil on, we started out with my tongue and finger replacing the dildo. After what seemed like an eternity of my tonguing her, with her telling me where to suck and play, she grabbed my head with her thighs, moaned loudly, bucked like she had when she had her first two orgasms, then gradually relaxed.

"My turn now," I said. She got up slowly and reached for the oils. She rolled me over and oiled my back, then my butt, even into my asshole.

Suddenly I felt the dildo.

She was ass-fucking me! I tried to pull away but she sat on me, twisting one arm behind my back to secure me. She worked the dildo around and around, in and out, keeping me pinned despite my best efforts to get away.

Finally she pulled it out and deftly lept off my back. I started to roll over but I was so sore I had to lay on my side. She smiled very wickedly.

"I'm not done yet, buster," she said. Well, I was, but she darted out of range, grabbed for the shopping bag, and produced a small box of condoms and a tube of KY jelly.

"Since you know how it feels to get it from behind, now you're going to give it from behind." I stopped being angry for the assault and started getting hard.

She grabbed my erecting cock and stroked it a couple of times until it was solid, then rolled a condom into it and lubed it up pretty good.

"Lube my ass inside, not just on the outside," she instructed, as she lay face down on the bed. I probably used half the tube and put my middle finger inside her all the way, and she said that was enough.

"I'm going to kneel and you're going to get between my legs and kneel too." As I moved into position she reached around her hips and grabbed my cock. She pulled me into position and shoved herself onto me.

I was amazed how smoothly it went in. "Slide in and out," she said, and I did, slowly at first, and when I started to go faster she stopped me. Four times she had me speed up a little bit, then slow down a little bit. After about 30 strokes of this I couldn't contain myself.

"Look out, look out, I'm going to cum, I'm cumming, I'm cummming!" and I did.

I collapsed onto her and we fell onto the bed. She easily slid me off to the side and shifted to face me. I tried to kiss her but she wouldn't let me.

We lay there, breathing hard, and I dozed. I woke to her removing the condom from my limp cock. When she saw I was awake, she made an exaggerated show of tying the open end in a knot and putting it in the small brown bag that the box of condoms had come in. Then she brought out another condom.

"It's BLOWJOB time," she said, like she was announcing a prize fight. She stimulated me and I soon got hard. She rolled the condom on in an exaggerated way and sat next to me.

Alternately stroking me and bending to put her mouth on me, Harriet went on for what must have been 15 minutes, knowing somehow when I was getting really excited, until she said "are you ready?"

I sure was, so she really got on me and went up and down. I thrust my hips in reciprocal motion, just like when I was in her ass.

"Oh man, oh man, this is it, I'm cumming, I'm cummming, oh, here it is," and I did it again.

By then it was close to 10. Harriet packed her shopping bag and allowed me to take her to dinner.

"How can I thank you enough for this? I won't leer at you at work, but I won't be able to forget what happened."

"Oh, by Monday you'll be able to walk straight," she said, and laughed, since I had been somewhat shaky in the apartment.

When we finished the meal she gave me a sweet peck on the cheek.

"Don't worry. You know what to do. There are a lot of your kind of fish in the sea."