Where it happened: my apartment
Langauge: English
Sex: Male
Rating: 5
Category: Straight
Harriet the teacher
I’d wanted to have sex since I was 12 but never was able to get very far with a girl. I went to a lot of mixers in college but never got much more than a sweet kiss. When I got a job in New York City after graduate school and was really on my own, with an apartment and some money, I decided that I had to start living.
Harriet worked in the same advertising agency, I in the art department, she writing copy. She was 23 to my 25, but she’d been in the city all her life. She took an interest in me and volunteered to show me around the “real” New York, the neighborhoods, the jazz clubs, and the little theaters.
The third time we were out we ended up in a small restaurant in her neighborhood and I asked her if I could go with her to her apartment. A strange 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 thought about. “But we’ll go there and talk.”
Harriet had a nice two-bedroom place in a very expensive building on the east side. She used one bedroom as her painting studio and the rest for living. She asked me about my life’s relationships, a conversation I’d never had outside the walls of my own head. I was hesitant, but soon enough I was telling her everything about my not-so-interesting past and my yearning to start living, including having a relationship, love, and sex. Since you’re gay, I said, can I ask you to teach me about how to attract and please a woman?
She said I was sweet and that she liked the idea of being my muse but that she was unsure of how helpful she could be. Harriet said that when she was in college, struggling about whether she was gay or not, she had had sex with two guys but found it unfulfilling. Only with another woman did she really begin to know her body and find enjoyment in pleasuring and being pleasured.
Uncharacteristically, I persisted, and she decided that we could try. We settled on the following Saturday afternoon, at my apartment.
When Harriet arrived around 2, she was carrying 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. First off, I was to take off my clothes.
Now while this is the fantasy every guy has, it dissolved when she made it clear that I was the only one getting naked. I stripped and she looked intently at me from various angles. “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 the bed, and took out a pair of barber scissors and a comb from her bag. “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.
Harriet kept up a running commentary as she went along, telling me that a woman makes decisions about her companion from the beginning. While no one is perfect, I would increase my chances if I looked attractive. She checked out my closet and dismissed most everything in it except for my jeans. Then she told me to get dressed.
Next she reviewed my conversational skills (good, she said), my posture (excellent), my manners (excellent), my work habits (good), and my self-confidence (weak). She said she didn’t know from our conversation where to begin, so she was going to assume that I needed to start as though I was in junior high school, which meant 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, fondled 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.”
I was so excited as my hands rushed to unbutton her work shirt and yank it out of her pants.
“No!” she said sharply. “You have to do everything slowly, lovingly. This isn’t a race. Here, I’ll show you” and she reached over and started unbuttoning my shirt, slowly with the top 2 buttons, then brushed her lips across my chest. “Take every chance to make contact.” When she had all the buttons undone she gently removed it from 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 forced 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 lifted 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.
She went into her bag and brought out a pastel-colored cylinder. “I like to use this with my lover. I’ll show you how.” For what must have been the next 2 hours I learned how to move the dildo all over her, around her pussy, even into her. She had brought out some oils and had me rub them all over as I moved the dildo. I was erect for the first half hour but then forgot about 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 when she had an orgasm (several times). Finally she said, “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 what I asked for and I had no claim to anything more. But here I was naked with a woman to whom I had delivered a lot of pleasure and she seemed indifferent to anything I might want. I laid down next to her, hips to hips. She started to pull away but I held her around the waist. I said “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. “I tried it with guys 5 years ago and it didn’t do anything for me.” “Well, how about something short of fucking? We can each do oral sex.” She inhaled and exhaled deeply. “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 before, 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 entering me from behind. She was ass-fucking me with her dildo! I tried to pull away but she held me down. She pulled it out and smiled very wickedly at me as I rolled over on my back. “I’m not done yet, buster,” she said. Well, I was, but she darted out of range of my grasp, grabbed for the shopping bag, and brought out 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 really angry for the assault and caught onto what she had in mind. And I started getting hard again. Harriet grabbed my erecting cock and stroked it a couple of times til 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. She arched herself up and told me to kneel behind her, between her legs, and put my cock into her. I was amazed how smoothly it went. “Pump in and out,” she said, and I did, slowly at first, then faster. She had me stop and then start, and maybe 10 or 12 more pumps and I came.
We collapsed on the bed, me on to of her. I rolled to the side and we faced each other. I tried to kiss her but she wouldn’t let me. We lay there, breathing hard, and gradually drifted off to sleep. When I woke up it was to her removing the condom from my limp cock. When she saw I was awake, she made an exaggerated show of tying the condom in a knot and putting it into the small brown bag that the box of condoms had come in. Then she brought out another one.
“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 into my cock in a very exaggerated way, put on a slight coating of KY, and sat next to me, alternately stroking my cock with her hand and taking the head of it into her mouth. She went on like this 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 to the head and went up and down. I thrust my hips in reciprocal motion, as when I was in her ass, and came pretty soon.
By then it was close to 9 p.m. We decided to go out to eat. When we finished the meal she told me that she was going home. I guess I knew this was going to happen but I was nevertheless was very sad. She said not to worry, there are a lot of my kind of fish in the sea. And there have been, but I will never forget the education that Harriet gave me.
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