CINDY:

Like many, I lost my virginity in college, in a college dorm room, to be specific. One single room with two couch beds. Literally, when the couches were pulled out, there was barely a foot between the beds. Even worse, the room was also right off the elevator. When Cindy and I fucked, we could hear people getting on and off the elevator. I worried they could hear us too.

Cindy was two years older than me. We met her through a co-ed flag football team. Cindy was classically cute, with short and small boobs. She was an English major and spoke with a refinement that I found very attractive.

In time, I met her parents. Her dad really liked me, and her mother too. She met my parents. They liked her. I thought she would be my one and only.

I really loved her, but having sex just off the elevator with people's noises just feet away made me nervous. Also, my roommate was prone to returning back at unexpected times. Between the elevator and the roommate, there was a sense of having to hurry. It was over all too quickly. In hindsight, maybe that is why, after a year and a half, Cindy dumped me.

RUTHIE:

Three years after Cindy dumped me, I went to graduate school a thousand miles from home. I shared an apartment, but unlike in the dorm, I had my own room.

Through school, I met Ruthie. Ruthie had longer hair and bigger boobs, but still on the smallish side. We went out on a few dates, but with my limited budget as a graduate student, they weren’t anything special.

One night, we watched a movie (for a buck!) in the student union and then went back to my place. My roommate was there with his friend. We ate some leftover spaghetti (graduate students eat a lot of spaghetti). The four of us listened to music, then Ruthie and I went back to my room.

Not too slowly, the clothes came off. There was much kissing and fondling. I fingered her clit and inserted a finger. Oh, she was wet! I was rock hard. I rolled over and mounted her. For the first time in three years, my dick was inside a pussy!! I could still hear the music from the living room. My roommate and his buddy, knowing what was going on, had put on Bob Dylan’s “She Makes Love Like A Woman.” That was too much for me. Far too soon, I came.

I already knew Ruthie was an assertive woman, but I was surprised when she whispered, “Lie down on the bed." Not knowing what she had in mind, I did so. Ruthie then positioned herself on my face. My cum dripped down. Sometimes Ruthie grinded on my face; other times she held my head up to her pussy

Years ago, out of “scientific curiosity,” I had tasted myself, but just a few drops. Now, as a young healthy man who had even jerked off in a few weeks, I was, in scientific terms, eating several cubic centimeters. Ruthie had an orgasm but had to stifle her moans because my roommate and buddy were in the next room.

Ruthie and I cuddled naked for a while, but as she had work the next day, she soon got dressed. I walked her to the door of the apartment. My roommate and his buddy were still in the living room. She said goodbye to them. I wondered if, telepathically, she told them, “Guess what I got him to do?” It was an irrational thought, but I felt my face start to blush.

I had the taste of cum in my mouth and wanted to desperately brush my teeth; however, in my small apartment, you could hear everything—even the sound of brushing teeth. I didn’t want to be obvious. Finally, the roommate’s buddy left, and the music stopped. I could brush my teeth and go to bed.

I found it hard to sleep. The mental image of licking up my own cum was unsettling. What kind of man does that? I’m not gay; I had no desire of being physically intimate with a man. The more I thought it, I went from being “unsettled” to being turned on. I still wanted to wet my dick, but I also wanted to give Ruthie more orgasms from oral after I came in her.

About two weeks after the night at my apartment, we had dinner at her place. Ruthie had a roommate but she was gone for the weekend. Ruthie and I made small talk through dinner but as young adults are prone to do, we got to the bedroom fairly quickly.

I told myself to go slow and relax, and that helped some. After some second-base foreplay, I went down on her. I took my time licking and fingering. I did not want to disappoint. She has a modest orgasm.

Then, for the second time in three years, my cock enjoyed the warm, wet inside of a pussy. I lasted more than a 100% longer than last time, but still less than a minute. Still, she had been satisfied with oral. We were both tired and fell asleep.

Unlike most graduate students, Ruthie had a job that paid decently. She worked as a manager for a nonprofit. Rutihe helped her nonprofit expand and was very proud of her accomplishment. Just about the same time, American Express sent her a new credit card. Credit card companies try to latch onto customers while they are still college students.

One Friday night, Ruthie called and said she wanted to celebrate her achievement at the nonprofit by “breaking in” her new credit card. She suggested we spend the night at a fancy hotel downtown.

By graduate student standards, Rutie was paid well, but I'm sure, like me, she had student loans. Even when not broke, I am not foolish with money. Spending a night in a hotel in a city I lived in seemed foolish. Still, as sex would be involved, I could not say no.

As my apartment was on the way to the hotel, we agreed she would pick me up in an hour. This gave me time to eat a peanut butter and jelly sandwich for dinner. I got paid just once a month. Payday was a few days away, and peanut butter and jelly were all I had left in the house. I was down to one dollar in my wallet.

I put on some clean clothes and waited for her. She arrived on time. I do like women who are, like me, punctual. I feel it is disrespectful if a woman is not ready on time. We drove to the hotel and checked in.

The clerk was surprised we didn’t have any luggage. Back home, I had a friend who had worked as a desk clerk. He said if a man and woman checked in without luggage, the woman was likely a prostitute. Since Ruthie was paying for the room, maybe the clerk thought I was a gigolo! I liked that thought.

The room had a lovely view, but even a great city view gets boring after a while. Not surprisingly, Ruthie and I began making out. When the outer clothes came off, Ruthie was wearing a matching black bra and panties. I think she also used in her new American Express card to buy some lingerie. She looked so hot. My dick was already poking out of my boxers.

At one point, she started to blow me. Maybe she wanted me to cum first, so I would last longer. I should have trusted her instinct. Instead, I slipped my hand in her panties. Oh, she was so wet.

However, my hand was too tight inside, and the panties soon came off. I went down on her, licking her and fingering. My face got wet with her juices. She had a decent orgasm. I lay over her and kissed her. She didn’t hesitate. She tasted her own juices, I suspect not for the first time.

It was then time to enter her. I entered easily. I started to fuck her. As I did, I happened to look up and see my wallet on the chair beside the bed. Broke, I felt so pathetic with just a dollar to my name. That thought didn’t help with my confidence in bed.

Ruthie started to play with my nipples. I have sensitive nipples for a guy. She knew that. It set me over the age.

I came hard. After making an initial interior deposit, I pulled out. My cock twitched on her pussy, and copious cum went on her pussy. When I finished, she stroked my hair.

I didn’t need any more direction. Her clit and outer lips were covered in cum. I ate it up. I was getting used going down on her, tasting the mix of her juices and my man seed. Unlike my cock, my fingers and tongue worked just fine. When the orgasm came, her legs quivered.

I slept well in that five-star hotel bed. In the morning we had breakfast in the hotel’s dining room. Five-star hotels have expensive food and I like a nice hearty breakfast, but knowing Ruthie was putting breakfast on the hotel bill, I just ordered toast and coffee.

Over the next few weeks, Ruthie and I saw less and less of each other. There were multiple reasons. She hinted that she wanted a threesome with a guy, and I wasn’t prepared for that. She also asked some very hypothetical questions about marriage, and in hindsight, I realized I didn’t give the answers she wanted. But most of all, we realized we didn’t share similar worldviews or the same taste in music, humor, or movies.

CHRISTY

Christy worked as a secretary in another department at the university. I had reason to visit the other department, and after some chit-chat at her desk, I asked Christy for her number. This was in the pre-cellphone era. She wrote her number and her address too! I folded the piece of paper and put it my pocket.

Once home and after trying to do some schoolwork, I called the number. It wasn’t Christy. I was devastated. I knew that sometimes women intentionally give out false numbers. It shook my already shaky confidence. Still, I was convinced that I hadn’t mistaken Christy’s interest. It was Friday night and I wanted to laid, so I drove to her place.

I stopped at a Blockbuster and picked up a VHS, (DVDs were still years away). I chose a rom-com, hoping that would set the mood. Christy was surprised that I came over without calling. Turned out, out of habit, she had written her old number, and she was glad I came by. I showed her the movie I picked out. She had just seen it, so we just talked.

Besides working as a secretary, Christy attended a local college. While she wanted a career, Christy was not the feminist, career-oriented woman that Ruthie was. Some day she would marry, have kids, attend PTA meetings, etc. That was fine with me.

We both knew we were horny started to make out. I got to second base, but respected Christy when she said no further. I was already tentyng hard. One final kiss, and I went home.

The apartment complex Christy lived in a had pool. As I learned later, Christy filled out a bikini very nicely. If I had to guess, she was a solid C cup. Christy had long black hair, a cute butt, and a slight Southern accent. An accent I found very sexy. While Ruthie or Cindy were cute, Christy was hot.

We had two low-budget dates (assuming the first night at her place didn’t count). On the third date, we make love for the first time. We got naked pretty quickly. After kissing and fondling. I fingered her and licked her. I wanted her to orgasm before I made my entrance, but she wanted my cock. It had been a two-month drought since Ruthie.

I lasted a little while, but not nearly long enough. Afterward, without hesitation, I went down on Christy. She was startled; no guy had ever done that before.

Christy kept a very clean apartment. I sensed she thought what I was doing was dirty. I told her, “Relax. I will stop if you want, but give it a chance.” I gave a long lick to her love button. Hearing no objection, I continued. As a young man, I had plenty of output to lick up on the folds of her pussy. Her orgasm built, and soon she was bucking like a horse. I spent the night, and Christy fixed me breakfast in the morning.

We did the “Blockbuster and chill” routine on a regular basis. One time I splurged and took her to a movie. I was still on a tight budget. A movie and popcorn were a luxury.

Most nights ended with me fucking her and going down afterward. Christy didn’t have a roommate, and her apartment complex was quiet, so there were no distractions. My stamina was building.

One night, we changed positions often, missionary, cowgirl, reverse cowgirl, doggy, and back to missionary. I felt I had the stamina of a porn star. Christy had multiple orgasms, and I felt like “a real man” as I didn’t have to go down on her afterward. When we were done, I said something like, “That was great.”

Christy replied with words that haunt me decades later, “Yes, that was good, almost as good as Dirk.”

Dirk was another graduate student. I knew him casually and knew he was also dating Christy. However, Christy was just a side chick for Dirk. His main squeeze was a visiting adjunct professor.

About a week later, I called and asked Christy out to dinner on Saturday. (I had hit Dad up for some extra money). Christy declined, explaining she had already made plans with Dirk.

I did not want to lose Christy. Unlike graduate students who leave town once they got their degree, Christy had family and deep roots in the city. She wasn’t moving anywhere.

As for myself, I was seriously considering a local civil service job (albeit not in my field) that paid well. I would be poor no longer! I could stay in the area. Dirk, when he graduated, would leave town for some academic post. Maybe Christy would be the one. Still, for near future I knew I had to a “grand gesture” just to remain Christy’s side piece.

Dirk had a job in the animal lab. To maintain experimental consistency, lab animals had to be fed at eight each morning, even on Sundays. I guessed Dirk would leave Christy’s apartment at seven thirty in the morning to feed the animals. I got to Christy’s place a few minutes before that and hid behind a staircase waiting for Dirk to come out. It wasn’t long before I saw him leave.

Shortly after Dirk left, I knocked on Christy’s door. She answered in a short robe. I asked if I could come in. She said, “Dirk was just here.” I repeated my request and rolled my tongue slightly. She repeated, “Dirk was just here.” I repeated my request, this time making a very exaggerated roll with my tongue. Without a word, Christy opened the door.

The robe fell on our way to the bedroom. I followed her hot ass to the bedroom. Christy pulled down the sheets and climbed on the bed. Accepting that Dirk was the better man, I began licking Christy’s pussy.

Cleaning up after another man was a mindfuck. I felt shame, yet I couldn’t have been any more enthusiastic. I tongued everywhere and fingered her too. Dirk’s cum was on my tongue and my finger. He had a very healthy output.

While eating her out, Christy encouraged me by saying things like "Keep licking” or "That feels so good.” After a while, full sentences then gave way to moans. She had a violent and quite vocal orgasm. I was rock hard and then went to mount her.

However, she said, "None for you, ‘big boy’—maybe next time.” The words “big boy” were hung in my ears. I am average in size. I’m sure Dirk was not.

Christy got up to take a shower. I lay there with a hard-on, tempted to please myself, but somehow knowing Christy didn’t want me to. It was a half-hour drive home before I could brush the taste of Dirk out of my mouth.

Christy and I continued seeing each other. Sometimes on Sunday morning for “breakfast” but usually on a Friday night.

One time on our way somewhere, she had to stop at her parents’ home. She declined to introduce me. I knew then where we stood. I turned down the local job and made plans to return home.

Before I left, we had one last fuck, and I went down on her afterwards, tasting her juices, mixed with my cum for the last time.

Once back home, there was another long drought, and I don’t mean a lack of rain.