First Time For Everything Pt 01

They say there is a first time for everything. I suppose that's true. Some we vividly recall, others we don't and there are those better forgotten. Many first-time events that we recall are only vague impressions. Then there are those that stay in our memories for a lifetime like our first love and sex. Yes, sex is among the most memorable first-time events.

I was shy in my early years. Asking a girl for a date was torture, even as late as high school. In my junior year, a girl asked me to a dance. I mean any girl making the first move was my kind of girl. She became my girlfriend. We were together for most of our senior year and after talking with the guys, I expected that she would be my first one, but nothing sexual was happening. It was a platonic relationship. I didn't have the nerve to do anything about it, especially since Kimmy said sex was for marriage.

It wasn't that Kimmy was cold or a prude. She liked to be kissed and hugged. That was as far as we went until my eighteenth birthday when my parents took us for a birthday dinner at a very nice restaurant. In our state, eighteen was the legal drinking age and my dad bought me my first beer. Kimmy had a glass of rosé. We both felt pretty grown up.

When I got in the car to drive her home, she said she had a birthday present for me. It was the first time I touched her tits. We were in the car and she nudged close to me pulling my arms around her. She kissed me and pulled my hands over her breasts. They were not small, but nice and full. It felt good and I wanted to do it again. Kimmy seemed to like it too. It wasn't much of a start but it was a giant leap for me.

On our next date, she took off her bra and pulled up her blouse so that I could kiss her nipples. Kimmy enjoyed the attention and rubbed my stiff cock under my jeans. This progression continued until she pushed my hands under her skirt so that I could finger her pussy. I was surprised at how soft and wet it felt. I was learning.

That was as far as she would go or maybe I didn't have the confidence to ask for more. The one exception was the week before graduation. I was so horny and she was so sexy in her tank top. I'm not even sure she was wearing a bra that afternoon, so I asked for a blowjob. Kimmy looked at me with a surprised expression but didn't say no.

My parents weren't home that afternoon, so I took her to my bedroom where we both undressed. I had never seen her completely nude before. She had an exceptional body with mature tits and a shaved pussy. I wanted to skip the blowjob and go straight into her pussy. She said, "No, one thing at a time."

Kimmy caressed my hard-on stroking it with her soft hand. That wasn't new, but when she went down on me, everything was like out of a dream.

She teased me by licking the tip of my cock and running her tongue up and down my shaft until she knew I was ready to cum. Kimmy didn't deep throat me but came pretty close. She would lick my precum and devoured every drop when I exploded in her tender mouth. I was surprised that Kimmy was so experienced at pleasuring me and even more so that she swallowed my entire load.

The irony of this situation was that she was very pregnant when we met at the Pizza Hut later in the summer. My best friend knocked her up when they both had been drinking at one of our Friday night parties. I was playing pool in the rec room while he was fucking Kimmy in the upstairs bedroom. I had no idea what had happened but was angry when she came downstairs and said she wanted to go home. I reluctantly left the party and took her home, no kisses, no blowjob.

This is one of those very memorable times to forget. So, I left high school a virgin and was very disgusted with myself that I never got into Kimmy. Something needed to change.

The old me didn't last long after high school. The new me emerged at a summer party before leaving for college. My parents had a cookout for a few friends. The party was a kind of graduation celebration for me along with a neighborhood get together. Among them was Delores, a married woman a few years younger than my parents. The day was warm, almost hot, so everyone was out by the pool. I didn't know Delores well but seeing her in skimpy bikini made me want to get to know her better. Finding a way to approach her was a problem as I fought my insecurity by drinking a couple of beers.

Sipping my third beer, she sat across the pool from me laying down on a chaise lounge. Her thong was tight against her pussy outlining every curve and crevice. I sat staring for most of a half an hour and couldn't take my eyes off her. Finally, I got my nerve up to go over and ask if I could bring her a drink.

"Oh, that would be wonderful," she said beaming a smile at me. "What are you drinking?"

"Beer," I said a little too timidly.

"Well, bring me a gin and tonic with a twist of lime."

"Yes, well," I said, "You'll have to show me how to fix it."

Delores looked at me for a few seconds, then she said, "I'd be glad to. A college guy needs to learn how to fix a girl a drink."

When she got out of the lounge chair, I got a glimpse of her perfectly shaped voluptuous tits. My heart skipped a beat and my cock surged needing release.

After she finished mixing her drink, Delores said, "You are Bob and Betty's son. It was so nice of them to invite us today. My husband, Wally, loves swimming pools. He thinks we should get one. I've seen you mowing the lawn but didn't know you were their son. You're so grown up. When are you headed to college?"

"I'll be going in the fall, Mam. Orientation is in August."

"Please call me Delores. What is your name?"

"Flynn but people call me Fly."

"Do you have a girlfriend, Fly?"

"Had one. She got herself pregnant by a buddy of mine."

"Really. That must have been a shock."

"It was and it still is."

"Maybe it's a good thing," Delores sympathized. "You're too young to be a father."

"Well, the way things have been going for me, I won't be a father anytime soon."

"Why do you say that, Fly?" she asked.

"I don't like to admit this, but I've never had sex with a girl."

"So you're a virgin. That's a shame. You are so handsome with a great body. Women would die to get you in bed."

I blushed and said, "Thanks. That's a real compliment coming from a gorgeous woman like yourself." I hoped I hadn't over-done it by saying gorgeous, but she was.

"Do you think I'm pretty. I'm not a young girl anymore. At thirty-six a woman loses some of her glamor.

"You haven't lost a thing. You look younger than thirty-six and sexy." Maybe it was the beer that let me say sexy.

"Well, Fly, you certainly say the right things. I could use more of that kind of talk. Come over sometime and I'll show you my pictures as a model. You wouldn't know it now, but I was Miss New Hampshire when I was nineteen. I think I won because of these," and she shook her body, so her boobs swung back and forth.

"Believe me, Delores, I'm not at all surprised."

That night, I couldn't get Delores out of my head. All I could think about were her swinging tits and the crease in her pussy. I needed some relief and pleasured myself before falling asleep.

It was unusually hot that summer, but the lawn still needed mowing. I was nearly finished when Delores came running out from next door with a glass of ice water. "You're soaked to the skin, Fly. You need to hydrate. I gratefully accepted the water and gulped it down. Handing back the empty glass, I got a good view of her tits. She wore a small revealing bra under a short house dress that was unzipped part way.

"Why don't you come over and get out of this heat and. I'll show you those pictures from New Hampshire."

"Sure, I'll be there in a few minutes, just gotta finish the parkway."

A soon as I got into her house, she practically ripped off my shirt. "My god you worked up a sweat. I'm going to toss this in the dryer and here's a towel to wipe yourself down. Gosh, you must be working out. You have a great body."

I flexed a few muscles just for the effect. I tried not to be embarrassed because it was clear she was hitting on me. I was anxious to find out how far it would take me. "How about a beer while you cool down?"

"Yeah, a beer would be great."

I could hear her turn on the dryer then open a cabinet to get me a glass. She returned wearing her bikini that was under her house dress and said, "I know we're not at the beach but when it's hot like this, I need to wear as little as possible. I take it you like the look."

"Yes, I love it but how did you know?"

"When I was at your place by the pool, you kept staring at me before we went for the drink. I'm so glad you came over to introduce yourself. To be honest, I kept an eye on you too."

She handed me a beer and opened a photo album titled "New Hampshire." I had expected to see them on her cell phone or computer, but they were professional color prints. Delores turned the pages and told me what the judges were looking for and why she posed in certain ways for each picture. Finally, she got to the swimsuit pictures and they were stunning.

I thought that was the end until she turned one more page. It was a picture of her topless. "Oh, maybe I shouldn't show you this," and she slammed the book closed.

"Come on Delores, that was beautiful."

She opened to the back page and explained, "I told you I did some modeling after I was Miss New Hampshire. This was the first shoot I did for a men's magazine. There are others but they are on our computer in the bedroom. Sometimes when we become really really good friends, I'll show them to you."

She smiled looking down at the bulge in my pants. "You know, Fly, my husband, Wally, is out of town next week. Maybe we can get together and we'll talk.

"Talk? What kind of talk?"

"We should talk about how you were able to get through high school a virgin."

"Okay, it's a short story. I can tell it to you now."

"Look, Wally will be home soon so it's best that you finish your beer. We'll have a chance to talk later."

I left with a hard on that was immediately satisfied in my bedroom. Maybe I was a virgin, but I wasn't short on the stick. If I had saved all my jizz, there would be a gallon jug full. But as for Delores, I had to find a way to up the ante and be a little more proactive. She certainly made no secret of the fact that she liked me.

That summer was good to me. I worked for my dad at his office entering data three times a week, went drinking with the boys, and of course did the lawn work when I wasn't jerking off thinking about Delores.

I decided to wear very brief gym shorts, no shirt and sandals when I knocked at her door one afternoon when I knew she was home. "Hello, Fly, I wasn't expecting you. I just finished my shower."

That was obvious as she was wrapped in a robe. "Is Wally home?" I asked.

"You know he isn't. I told you he was out of town this week."

"That's why I'm here, Delores. You know, so we can have that talk and be friends."

She looked confused for a moment, then said, "You came to see my other pictures, right?"

"I came to see you."

"How would you like to see me?"

"Without that robe," I said with my heart pounding. I'd never been that assertive before in my life. How would she react? I wondered.

"You mean like this?" and she dropped the robe.

"Yes," I said. "Exactly like that."

Her tits were marvelous; her pussy was shaved bald; her smile was seductive. Delores was the perfect model for a men's magazine.

"Maybe we should continue this in the bedroom," I said in a slightly elevated tone.

"Maybe we should but I'm expecting a friend in a few minutes. Can you come back tomorrow afternoon?"

"I work tomorrow. Maybe tomorrow night."

She gave me a pensive look and said, "That would be fine but after dinner around eight-thirty."

"Okay."

After leaving Delores standing in the doorway nude, I was curious about her friend. I watched from our front window as a man pulled up on her driveway. He was tall with greying hair. He wore a tie and sunglasses so I couldn't tell who he was. He slipped in the side door but didn't come out to his car for nearly three hours. I had a view of the side door from my bedroom and watched as she gave him a goodbye kiss. He wasn't wearing his tie or sunglasses and the top three buttons on his shirt were open. It looked like she still wasn't wearing anything. I recognized him. He was the school principal.

Oh, did I ever feel like a jackass, tip toeing around trying to get into her cunt. She was no angel and now I know what I needed to do. I needed to act like a man.

Eight-thirty didn't arrive quickly. It was like waiting for a snail to cross the road. Again, I wore gym shorts but this time without briefs. I had on a distressed t-shirt and sandals like before. This wasn't going to be a test of my virility but my determination to overcome my insecurity.

I showed up at her door five minutes late. She was ready for me giving me a passionate kiss and wearing a nightgown.

"I hope you don't mind me being so informal tonight. I thought we should relax and enjoy the evening. I'll show you the pictures after we have a drink."

"Fuck the pictures. Fuck the drinks," I said. "Take off that nightgown. I want to see the live and in-person version."

I didn't wait for her reaction and pulled it over her head. "My, Fly, you are a bit aggressive tonight. I like that in a man."

I pulled her into the bedroom and sat her on the edge of the bed, pulling her legs apart. I went down on her hoping I was doing the right thing. Her pussy was silky smooth and sleek. I found her clit and tried to duplicate what men did in the porn flicks. She seemed to enjoy it.

Hop on the bed, Fly. Let me see that cock of yours. I dropped my shorts and rolled next to her. "Oh Fly, you have a nice one. I kept hoping you had a big cock ever since we met by your pool. I'm not disappointed. After I pleasure you a little, show me what you can do with it."

My hand work at home helped me hold back for a while after I gently penetrated her wet pussy then thrust myself inside until I'd bottomed out. She squealed, "That's it, Fly. That's how I like it. Please don't cum too fast. Fuck me like you would your girlfriend."

Her encouragement didn't help my powers of resistance. I could feel my insides swelling up ready to burst and when she said 'fuck me' I just exploded. She didn't seem to mind. "Oh oh, oh, that's good. That feels so good."

I laid on top of her still impaled in that sweet warm pussy. She told me to keep it in as long as I wanted. She liked the afterglow when a man had cum and kept his fat hard cock lingering inside her.

"How did you learn to eat out a lady like that?"

"It's something I saw in porn videos."

"Yes, they certainly are good for educational purposes. Anyway, now we can have that drink," she said when I finally pulled out with a limp flaccid penis. "We can come back here later. You're young so I'm counting on you to recover quickly. That's why sex with young guys like you is so rewarding."

I tried the gin and tonic for the first time. Beer was better. We talked and talked. I said she was a beautiful sexy woman and told her I knew her friend.

"What friend?" she asked.

"It's our school principal."

"Fly, you have to understand. Principal Vincent and I have been friends for a long time. Look, I never said you were going to be my only one. I like cheating on Wally and Wally gets off hearing about the men I fuck. I like men and always have. It helped me win the Miss New Hampshire contest. You know, Fly, Wally isn't any more faithful that I am. That was part of our prenup when we married. He isn't on a business trip this week. He's shacked up some bimbo at our vacation home. More important though, how was it for your first time?"

"Fabulous! I've really been missing out."

"Drink up. Let's see how we can make it even better the second time."

It was. Delores showed me all the positions she liked, and they were exactly what I liked. The third time I came, she wanted it in her mouth. She had to wait a long time before I let loose with a modest load on her waiting tongue. I was drained but Delores was delighted to have cum in her mouth so she could share it giving me a deep tongue kiss. It was the first time I had tasted cum and it was my own!

From then on when I saw Wally, I made a point of greeting him with a friendly hello when he was taking his morning run. One day he asked if I'd like to run with him. The next morning, I was running and talking with the husband of the woman I had fucked a few days earlier.

Wally got to the point right away. "I want to tell you, Flynn, how much I appreciate you taking care of Delores when I was away. She said you were very good to her."

It surprised me that he would be that open minded without a hint of anger. Wally appeared to mean what he said. "Your wife is a very considerate beautiful woman, Wally," is all I could say.

"Delores said you are going to college soon. When do you leave?"

"In a week. I'm a little nervous about it."

"Delores and I are flying to Arizona tomorrow to visit her parents. So, let me say goodbye and good luck."

I eked out a weak goodbye and said, "Thanks and have a good trip."

****

The first few days of college was a whirlwind of events. It amounted to starting a new life by getting settled in the dorm, signing up for classes, buying books, social events, and getting to know the campus. My roommate was Tyler, a six-foot seven-inch basketball player from Chicago. He was on scholarship and didn't appear to be a scholar. I soon learned that the girls loved him, and he loved them.

At first, I left the room while Tyler romanced his date, but it became an almost everyday affair so occasionally I would stay and pretend not to watch. He didn't seem to mind. I didn't get to know how the girls felt about me being there until I got to know Bonnie. She was in my math class and was working on being a high school math teacher. Sex with her was like applying a mathematical algorithm. There was little romance and no spontaneity. We did it by the numbers.

I remember her saying on our first date, "Look, Fly, if we have sex, you have to wear a condom. I don't do it with guys without a condom. And I like being on top. Can you live with that?" She had it all worked out. Sex was the vanilla variety but at least it was a way to get off without using my hand. The highlight of fucking Bonnie cowgirl was watching her sizeable boobs giggle as she rode my cock. It seemed out of character, but she came quickly and often. I liked that.

Tilly Taggert from Omaha was a different story. I didn't date her until second semester. By that time, Tyler had moved out into an apartment with some of his teammates. I had the dorm room all to myself. Tilly would stay the night and wanted sex before going to sleep and the first thing in the morning. She didn't have a preference for position. Tilly wanted to do them all. She kept reminding me that variety was the spice of life. I got plenty of spice that semester.

I was home for the summer working for my dad as an apprentice. Unlike the previous summer when I worked only three days a week, this was full time work. There was less time to visit Delores, but I made a point of hooking up with her on the weekend to demonstrate what I had learned in college. I couldn't get enough of her pussy and she must have felt the same about my cock. Delores complimented me on my new skills and now lucky she was to have me as her neighbor.

It was that summer when Delores finally showed me her modeling pictures. Delores had only said she worked for a men's magazine. What Delores meant was that she did porn.

The first few shots in the slideshow were what might be expected in a man's magazine. Delores wore seductive clothes followed by bikini pictures. In the next set she was topless, then nude. The pictures became increasingly more lurid with her legs apart showing every detail of her pussy. The final sets were fuck pictures. It included a variety of positions and a lot of different men of all ages and colors.