Even though my mom lived on the upper West Side, I moved into a dorm my freshman year at NYU. Mom had plenty of money after the divorce from dad, an insurance executive, and she figured that I would concentrate better on my studies if I didn't have to live at home. I agreed and relished the full college experience in Greenwich Village.
But there was one problem with living in the dorm with two roommates: I was perpetually horny. After fucking nearly every day over the summer, my high school girlfriend went away to Fairfield University, so I only had sex about once a month when we managed to visit each other. I couldn't jerk off in my room because guys were always around. The bathroom was serviceable, but I liked to spank to porn. And there was no graceful way to sneak a magazine into the bathroom with me. This was in the 2000s, before smartphones. I would sometimes go three days straight without beating off, waiting for privacy. That makes an 18-year-old a little twisted in the head, especially after he smokes pot with his friends.
Luckily, Manhattan was filled with adult video stores with private viewing booths. I got into the habit of going to them after dinner a couple of times a week. This one place that I particularly liked was all the way down by West St. The viewing booths were equipped with two-foot by two-foot windows on each side. They were sort of like a glory holes, but way bigger. Each window had two sets of shutters. When someone opened his side of the shutter, a little red light would go on in yours, signaling you to open the shutter for anonymous sexual activity if you wanted. It worked like a confessional, but for sex.
I'm not normally gay, but sometimes I indulged instead of jerking off. I liked getting my cock sucked as I watched porn. And men happen to give good head. I usually opened up my side of the window and waited for someone willing to get his face fucked. I never sucked someone else's cock, though. I shut my window right away when someone poked his pecker through. I'm selfish.
Anyhow, my real preference wasn't for gay stuff. And one night I went there, I had another opportunity. I was high that night and hadn't nutted since a quick bathroom jerk two days before. My dick was hard the entire way to the shop.
I saw the light come on and I could feel my pounding heart shake my body at the prospect of finally getting off. When I opened the shutter, what was waiting for me was not the face of a gay man, but a woman's brunette bush. I could only see her waist, but by its width and an ample pouch below the tummy, I could tell that she was in her mid-forties at least. I thought she would drop to her knees to blow me, or perhaps she wanted me to eat her out—two tasks I was more than willing to do. But she instead handed me a condom, stuck her big round ass in the window, and bent way over. Her pussy peeked underneath, the folds were swollen and gaping open. The flesh inside her cunt was fire-engine red. She had been fucking and wanted to get fucked again.
I never heard of a woman doing this. My penis throbbed at the thought: A woman so slutty she sneaks into viewing booths for anonymous screws from behind. I was so turned on I was afraid I'd cum before I even had the condom on.
I palmed her pussy and plunged a finger in to tell her another cock would soon arrive. She stuck her backside as far through the window as she could. I grabbed the sides of her hips. I worked my dick in. It was easy. My girlfriend was so tight that I had to take my hand and force myself in. This woman's cunt was like a black hole, engulfing everything that came near it. I fucked her slowly at first. My dick and my pubic hair were dripping in her musty juices.
I hunkered down after a minute and really went for it. Fucking her like a jackhammer rang her bell, I could hear her muffled screams through the wall. I didn't last very long at that pace and I came harder than I ever did with my girlfriend. I pulled out, the condom was laden with my big load and glistening with her juices. The woman passed a note to me.
"I am here from 7 to 9 every Tuesday."
All I could think about all week was cracking that ass again. The next time I went to the shop—at 7:15 and at the same exact stall-I opened the window right away. I could hardly wait for the other window to open. While I waited, I wondered: "Would she be here? Could she have skipped a day? If she doesn't show, should I just keep coming every Tuesday until she does?" My thoughts were interrupted by the sound of the opening window.
It was her again. And, again, she did her routine of handing me the condom and poking her ass through the window. So she would know it was me, I jammed my middle finger up her cunt like I did before. But this time I twisted and turned and really finger banged her. I replaced my finger with my penis and this time kept the slow fuck going. I was savoring the fuck. I spread her ass cheeks apart and gaped at her asshole. I was surprised to see it looked tight and unused. I wondered for a moment if she would ever let me in there. The thought overwhelmed me. I came as massively as I did the week before.
That women was on my mind constantly after that night. Though the random fuck were an unimaginable thrill, I began to wonder who she was and what she was like "in person". I had fantasies about bringing her back to my dorm room for face-to-face sex. But her face itself was still a blur in my fantasies because I had never seen it. In my desire to give her an identity, I searched for her passively in my daily wanderings around the city. When I walked around town, I checked out women's butts like a pervert. Every older woman with a big ass gave me a boner. Each one of them could have been her. And I wanted to screw them all.
That following weekend, I went home and had dinner with my mother. Of course, I was distracted with thoughts of my new sex exploits. Perhaps it was my new found habit of looking at all women at waist level, but whenever my mom was walking around, my eyes darted right to her rear end. Her form-fitting slacks revealed the kind of mid-section that I had become obsessed with. Her ass was the right size—plump, round, and still shapely. Her hips were about as wide as the booth woman's. I got a boner right there. But immediately, I blotted the thought from my mind. I saw a lot of women that week that matched just as well. And besides, my mother would never do such a thing: she barely started dating after the divorce.
I arrived punctually again at the shop the next Tuesday. And the routine played out exactly the same way, except this time, I gave her pussy long strokes with my tongue from behind, my nose buried in her ass cheeks. When she started to twitch I plunged my dick into her and pumped her hard. I didn't even bother starting off slowly. She groaned loudly and squirted more juices than I did when I came. I loved that I was giving her pleasure. I was trying to woo this anonymous woman, and I think I was succeeding.
I noticed something else, too. The woman used clear nail polish on relatively short women's fingernails, just like my mother. This wasn't much of a clue, I know. Lots of professional women do this, especially if they aren't very dainty. But it made me paranoid nevertheless.
Out of curiosity and to prove myself wrong, I gave mom a call on my flip phone when I left. She wasn't home. I would usually expect her to be in the house that time of night. I told myself there was an innocent explanation, though. I left a message telling her I would have lunch again this weekend.
That whole week I grew more worried. I thought about how I could eliminate my mom from contention as the woman from the booth. It seemed so incredibly unlikely given her personality. But I had no logical reason to say with certainty it wasn't her. I thought long and hard. I never really heard the woman's speaking voice, only muffles through the wall. There had to be some way I could know for sure. I thought about hiding someplace the next week to watch when she exited the establishment, but there was no place I could wait and watch the door unnoticed on the block. It only had a few parked cars and no other storefronts or restaurants. I didn't want to be seen lurking in front of a porn shop.
Then I decided I needed to try to find a way to get into her house alone so I can riffle through her things for clues. I brought books over on Saturday and told her I would stay the weekend to study because my roommate had family over.
As she milled around the house fixing lunch and doing chores, I couldn't help but see her in a different light. It wasn't so much that I became attracted to her, it was that I was starting to see all women over forty as sexual beings. Glancing at old pictures, I realized how much of a hottie she was when she was young, and also how attractive she still was. She was curvy, showing off her cleavage in a photo from a dinner party. Her breasts were a solid "C" cup. Another photo of her in dungarees showed an ample ass. How my father must have enjoyed screwing her when they were both in their 20s! Putting on a few pounds over the years only accentuated her curves. She must get hit on a lot, I thought.
While I was there, I couldn't help but peek at her ass as she bent over in front of me, revealing a little panty line. I imagined myself pulling up the skirt she was wearing, pulling down the panties, and fucking her right there. My dick twitched in my pants. It was unnatural and unusual to think that way. I had to fight those urges. I couldn't get caught staring, either. It was all so strange.
She headed out to run errands until dinner. I knew that I had a few good hours to search her apartment. First I looked through her closet and drawers. The idea was that I would make a mental note of her wardrobe. If I could peer into her booth during the next session and recognize an article of clothing of hers, that would be something. I was also looking for lingerie, condoms, sex toys, anything that would indicate that she was living a secret romantic life. I came up with nothing.
I went searched the hamper. All the panties I saw in there seemed normal enough, just the regular cotton numbers women wear every day. I don't know what come over me, but handing her soiled underwear turned me on. I held a pair up to my nose and took in her scent, it was just like the woman in the booth. I had a full erection. I lied down, covered my face with her underwear, and jerked off while I inhaled her musk.
I replaced everything exactly as I found it. Then the idea struck me to check the garbage. I didn't know what I was looking for, but surely, I might notice something. I plunged in. Buried deep inside the garbage pail, tucked into a plastic bag, was another pair of panties, very different than the others. They were lacey and cut smaller. They were filthy and still a little moist. And from ring of stain around the backside and extending way to the front, I could tell they were soaked in her feminine juices. They also reeked and had public hairs glued to the inside. My heart pounded. This might not necessarily be a relic from the stall, but clearly by mother was doing something dirty somewhere.
That Tuesday, I was determined to get some definitive clue. It drove me crazy that a possibility remained. I did the same ritual as I did all the other times, but I ate her out for long time and snuck peeks between her legs and into her stall to see anything I could under the blue light of the video screen. I saw a tan overcoat just like my mom's slumped over a stool with a pair of my mom's dungarees on top of it. I almost fainted. This was no coincidence!
