Category: first times

Annas First Time

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I have a girl that works for me in my law office every Saturday. Her name is Anna. She’s such a delight, a sweet innocent young girl. Saturday is the day I’m always there alone catching up from the week while Anna does all my filing for me. Anna is really quite a cute little girl; at least that’s the way I see her. She’s about 5′ 7″ tall and very, very slender. I figure she only weighs about 100 pounds. Anna just turned eighteen a few weeks ago, but you’d never guess that. She looks like she’s only 14 or 15 years old. Maybe that’s what makes her so exciting to me. She’s got a great body with small breasts maybe only a 30 or 32 inch chest. Her waist is very thin perhaps 22 inches if that, and hips matching her attractive figure. But then there’s Anna’s rear end. Yes, her ass. Her ass is what always catches my attention. Many Saturday afternoons I’ve stared at her while she was filing and just gazed at her well-proportioned bottom.

I always loved those days when Anna would wear a blouse and a short skirt, especially her pleated skirt. When she wears that, she looks like she’s ready for cheerleading practice. Needless to say I have a hard time concentrating on my work those days. I would spend most of my time watching Anna and those smooth slender legs. Every time she bent down and her skirt rode up higher, I’d catch a glimpse of her soft supple thighs.

“My God,” I would think. “Look at those gorgeous legs.” You talk about driving a man nuts; well this is what was happening to me. Sometimes when she sat at the table next to my desk her legs would be apart a bit and I would get a peek up underneath her skirt. One day she inadvertently had her legs spread allot and I could see everything. “Pink panties,’ I said to myself. “What a fucking cute girl.” It took allot of willpower to keep from grabbing her and feeling her up.

Anna is a very proper young lady always being quite polite and appreciative of having a job and working for me. Although I’ve daydreamed many times of having a go at her petite gorgeous body, I never really thought anything more of it or that anything could happen because she always acted so professional. She did her work, went home and that was that.

Well this one Saturday everything was normal. Anna was filing some papers bending down to the bottom drawer and I was staring at her cute ass as I usually did. And she had on that pleated skirt. I must have been daydreaming more than usual looking up her dress, because the next thing I realized was Anna staring right back at me. At first I was a little embarrassed for being caught staring at her, but she just smiled and looked back at me. However, what started out as a simple glance at each other soon became a long inviting stare. I was wondering what she was thinking and I was convinced she was thinking about my nasty thoughts.
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Mommy Daughter Frat Party

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This is true story that was pasted to me by a women “friend” while we were lying in bed after making love. It was in response to a question I asked her about any interesting experiences she had had and could share with me. Her husband is not aware of this event or the times that we have shared together.

My daughter and I have always been best of friends; even through high school we were able to share with each other all our experiences and concerns. When she left for her freshman year at college 150 miles away I felt a hole in my life with her absents. About six weeks after she started school I decided to visit her for a long weekend. I ask my husband if he wanted to go with me, but he declined telling me it would ruin Kim’s and my opportunity to send quality time together. I was happy that he declined because this left Kim and myself free to talk and spend time together as mother-daughter, best friends. I left to visit Kim on Thursday afternoon knowing that she would have class on Friday for part of the time and I could look around the campus. Our plans were for me to stay in her room and be part of the college crowd again, even if just for the weekend. When I arrived I met Kim and was introduced to the other girls in her dorm. I felt like a young college student again, having to share a common bathroom and hearing the constant girl talk in the hallway.

I asked Kim and her friends if there were any big plans for the weekend and one of her friends said that some of the group was planning to go to a local frat party off campus. I asked Kim if she had planned to go and she “no” because she thought I wouldn’t be interested in a frat party, with a lot of drinking and loud music. After a short pause I told her that I wouldn’t mind going, if she wouldn’t be embarrassed having be there. So the plan was to go to a college frat party on Friday night, my first college party in many years.
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2 Guys Are Better Than 1

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My best friend Jake called me and asked if I’d fly up to visit him to help him move. I never turn down a free trip so off I went. We spent most of the first day putting all of his stuff in boxes, and by nightfall we were both ready for a few beers. We met up with some friends of his, including Darcy, a beautiful redhead with a great body. I flirted with Darcy all night as we went from bar to bar. I thought I was making pretty good progress, even though Jake kept giving me signals to back off, but I just figured he was jealous. Finally, I asked Darcy if she’d ever slept with a guy she’d just met. She laughed and asked if I’d ever slept with a lesbian. I stuttered, not knowing how to respond. She replied, “If you get the chance take it, we’re excellent.”

“Do you exclusively sleep with women, are do you sleep with men also?” I asked, hoping I still had a chance.

“I’d never do a guy. Woman are just so much prettier.” I had to agree with her, even though my hopes for the night were dashed. After that however, Darcy and I were still just as flirtatious, maybe even moreso now that I knew I wasn’t going to get any. Jake still had no idea that I knew, and kept trying to warn me, I played dumb and let him think I thought I still had a chance. The bars all closed down, and the whole group, about nine of us, all went for a night cap at a nearby apartment. We stayed up most of the night telling embarrassing stories and drinking. Darcy was sitting on my lap while Jake continued to give me silent warnings. I got up to use the restroom, and when I returned Jake had taken my place under Darcy’s beautiful backside. Knowing I wasn’t losing out on anything, I simply took the available seat and rejoined the fun.
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Ariel Feels Daring

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I have always been a selective girl when it comes to sleeping with a guy. All through high school and college, I had mostly dated Asian guys, being of Japanese ancestry. I’ve dated a few white guys but have never slept with them. My parents, 2nd generation Americans, were always strict with me, so my sexual experience was pretty limited before college, and even then it took a while for me to feel comfortable with my sexual side. Now that I’m 23, I feel that I have really hit my stride, sexually speaking. I can say that in large part to what happened to me last weekend.

It was last Saturday that my best friend Eloise called me – she wanted to go clubbing that night, and who was I to say no? I love to go dancing, and there’s always a chance to meet some cute guys. That afternoon, I went to the manicurist – I always get a weekly manicure and pedicure to show off my long slender fingers and the toe cleavage on my small feet. Today it would be a French manicure for my fingernails and silver polish for my toenails. Then I went home and got into the shower, making sure I was freshly shaven. I left only a tiny wisp of hair above my pussy. I toweled off and dried my hair – I have the typical Asian straight black hair, which I keep long, down to my shoulder blades. Today, I decided I’d put my hair up in a bun, which I secured with two hair sticks. Next I put on makeup. I have raised, thin eyebrows, with large brown eyes that are round compared to many Asian girls, so I used a little eyebrow pencil and some mascara to highlight my large, round brown eyes.

My lips are fairly full, so I applied some fire engine red lipstick. I put pearl drop earrings in my pierced ears and put on a double strand pearl choker around my neck. (It’s all costume jewelry, but who knows the difference, really.) In my lingerie drawer I picked out a pair of black lacy panties and a matching strapless bra – 32C, not bad for someone with my genes! I caught a glimpse of myself in the mirror and wondered if anyone would see me like this tonight. It’s vain, I know, but sometimes when I’m at home getting dressed to go out I like to stand in front of the mirror and look at my body. For being only 5’1”, I think my best asset, though, are my legs and my butt. I’m especially proud of the little open space between my lean upper thighs right below my pussy. Any girl who has that little space right there is keeping her thighs in good condition, don’t you think?
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Football Memories

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Reminiscing is a good thing. I do quite a bit of it. I especially like to reminisce about my college football days. It’s been 9 years since I graduated college and joined the working world. Although my dating life has been good, nothing has happened to me since that can compare to those days of football glory. I remember the parties, the perks, the fame, the women…what a wonderful experience. Pussy was so plentiful in those days. Young, gorgeous college girls with their tight bodies practically threw themselves at me and my teammates.

I was the starting tailback for my school. I was in much better shape in those days. I stood 6 ft 2 inches tall and carried 225 lbs of rock solid muscle. Being a large young black man, some found my presence to be a bit intimidating. I was the prototype Mandingo warrior, complete with an 11 inch thick black cock for stretching young white pussies. I was pretty proud of my dick. Still am. Not only is my cock thick and long, but it sports an assortment of thick veins, giving it a muscular and powerful look, and a doorknob-sized head. I’m also a heavy cummer. I have been known to spray women with such huge loads of love juice as to be able to fill a drinking glass to the brim.

My school had very wealthy alumni. Many of them were crotchety old white men who love football and were willing to pad the pockets of the players to show their “gratitude” for continuing the school’s winning tradition. I received a king’s ransom in cash and gifts in those days. Of course, this was all against NCAA rules, but so what. Most of the players, although receiving full scholarships, didn’t have enough spare change to afford to take their girlfriends to a movie. We believed we earned our perks, and kept it all under wraps.

During one of the many “socials” that we have with alumni, I met the college’s most wealthy benefactor, a Texas oil man named Mr. Clive Jones. Mr. Jones was 77 years old and looked to have one foot in the grave. He was a nice old man though. We talked a bit about football and my future plans before he slipped me an envelope full of cash. It was my freshman year at school, and I was totally taken aback by this gesture. He looked at me and smiled. At that moment, a beautiful young blonde came our way. She wrapped her arms around the old man and gave him a kiss on the cheek.
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Sweet Revenge

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Let me introduce myself. My name is Adam. I’m 29, and have been working the City stock markets as a dealer for the last six years. People say that I am arrogant, but to be successful at what I do, one has to have a very forceful personality. I met my wife Christine, or Chris for short, at a works party three years ago. The moment I saw her tall, athletic figure with her long flowing blonde hair, I just knew I had to have her. I usually get what I want, and a few short months later we were married. Chris also has a very stubborn streak, and our inevitable arguments were of a very explosive nature. As I sit here now, thinking back to the events of last night, I can hardly remember how the argument started. Let me see if I can recall some of the details……

It all began last Friday evening as I arrived home from work. As usual, I had stopped off at a local bar in the city for a few drinks with some colleagues, before braving the commuter ride home on the train. As I entered my house, I could smell the aroma of home cooking and knew immediately that Chris had been trying out a new recipe. As the meal progressed, assisted by a couple of classes of good claret we talked casually about our respective days.

“By the way.” I said casually. “We are going to a party tomorrow night. Clive at the office is having a whole bunch of us over to watch the match on cable.”

“What? You didn’t say anything. I had plans for tomorrow!”

“Well you will just have to cancel them. Everyone will be there, and so will we!”

The argument continued late into the evening and into the following morning. As I have said, I usually get my way, and by lunchtime Chris had reluctantly agreed to go to the party. For the whole of the afternoon, she point blank refused to speak to me, ignoring any of my half hearted attempts at reconciliation. By 7pm we were both showered and changed and heading for Clive’s house in the country. Chris had mellowed a little, but was still obviously extremely angry with me. What the hell! I thought, I could just watch the match while she sulked!
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Seducing Greg

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Greg really wasn’t into dating in High School. He was heavily into his many activities, especially music, and besides he was too shy to pursue dating. So, off to college he went, inexperienced in the ways of girls and dating.

After being at the university for 6 months, he first met Lisa at work. Lisa and Greg had both been assigned to student work in the Music Library. They were both music majors. Greg was a smart ass know it all conducting major, while Lisa was a confidant and out going sophomore who played the cello. They would talk about music and school gossip during their hours working together. Greg lived in the scholar dorms where he had a single room and communal bathroom. Lisa lived nearby with 3 other girls in an off campus rental house.

Greg had a rather extensive record collection and Lisa and he often discussed the performance interpretations by various artists. Over time Lisa and Greg sometimes walked home together after a stint working at the library and would stop by Greg’s room to listen to some recordings. Lisa eventually began to occasionally stop by unannounced and they would listen to music or just talk. Lisa enjoyed being with Greg, he was interesting to talk to enjoyable to be with. Greg had blue eyes with sandy colored hair and was medium height and slim body. Lisa liked his warm smile and thought he had a great set of buns.

Lisa was interested in Greg but was sort of dating someone else. Also, she never heard Greg talk about girls or old girl friends. Was he not interested in dating? Was he gay? Lisa even quizzed some of her gay friends to see what they knew about him. Other than agreeing that Greg did indeed have a nice ass, they were unaware of his leanings either way. Lisa occasionally mentioned her boyfriend to Greg hoping to get a reaction out of him, or have him remark about some of the girls he might have dated, but he said nothing.

Greg enjoyed spending time with Lisa. She was a smart girl and didn’t let any of his smart remarks go unchallenged. Lisa was short, about 5′ 2″, slim with black curly hair and brown eyes. She had nice “college girl” figure, with firm breasts and a cute butt.
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Surprise For Kim

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Justin took me there because he wanted to buy me something sexy for my birthday. I expected Victoria’s Secret or someplace like that, not the adult book store. But there we were, he had picked out a black crotchless teddy he said he would like on me, and so I went into the fitting room to try it on. I had, and it fit well. I thought to myself that I would have to get some stockings that go with it. I was just finishing getting dressed in my normal clothes again when I heard the door to the fitting room next to me close. Could hear someone moving around, then a hard cock poked through a hole in the wall that I hadn’t noticed till just then. Justin must really want to be naughty, and I felt a little naughty myself right then.

I reached out and wrapped my hand around his hard cock, it really was a beautiful piece of meat. About 7 inches long, which is perfect for me, veiny with a mushroom head. I was squeezing and slowly stroking it, Justin loved when I teased him like that. He pushed against the wall harder, trying to get it all through to me. Thinking about how easy it would be for someone to catch us was getting me wet. From the way he felt in my hand it was having the same effect on him.

I bent toward him, holding it in my hand so just the head was poking out. I squeezed tight, and licked the tip. I opened my hand and licked all the way from the base to the tip, which made him twitch. I reached down to play with his balls, wiggling all the fingers of my left hand against them as I put my mouth around the head of his lovely cock. I stayed there, tickling his balls while I sucked on the head for a few seconds, then I slowly slid down his pole. He pushed a little more, trying to get inside my mouth. I took him as deep as I could with the wall there, my nose up against it. I sucked on him like that for a minute, feeling him throb and twitch in my wet mouth. My other hand was now pinching and playing with my right nipple, and I could feel that my panties were getting wet.
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Heather Has a Virgin Ass

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Over the past few weeks my secretary Christine has been telling me about a girl she met at a dress boutique. She stopped there one night to do some shopping and met this girl Heather who worked there. Ever since then, Christine has been talking about her. You see Christine has this fantasy. She constantly wonders what it would be like turning a sweet innocent girl into our little plaything. Now we really didn’t think that we’d ever meet anyone to make that fantasy come true, but it was nice dreaming about it.

After meeting Heather that night and few more visits to the boutique, Christine desperately wanted to ask her to join us for an evening. My nasty little secretary told me how much they talked about the many things we did at home and in the office. Heather apparently seemed interested and asked allot about me. I wasn’t surprised when, one evening, Christine told me that she had asked Heather to join us and she accepted. The arrangements were set for this Friday night. I have to say, I was really excited about it and Christine was too.

At about eight o’clock when the doorbell rang, Christine answered it. I couldn’t believe what I saw. This incredibly cute blonde walked in. She wore a simple summer dress that hugged her little schoolgirl curves so nicely. And that’s exactly how she looked, like a little schoolgirl. I couldn’t imagine that sweet young thing wanting to join in with Christine and I. I just stood there staring at her.

Christine properly introduced Heather to me explaining that she worked at the dress boutique. But I knew all that, it was just the formality and breaking the ice so to speak. Christine went on saying that she had just turned eighteen and worked there to help with her college expenses.
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Alone At The Movies

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I’ve got to tell you about a most incredible experience I had last week. Ok, ya, sure, you’re thinking I made all this up. Well, read it and believe!

There it was, a crappy Thursday night. I was feeling anxious and itchy and decided to go to the movies. I wanted to be alone; what better place than in a theatre? The wife was in her usual “I couldn’t care less” mode, so I decided, “frig her”, I’ll go by myself. I always wondered what it would feel like to go to the movies alone; wondered what people would think.

As I entered the darkened theatre, popcorn and soda in hand, I slunk down into a seat in the middle of the last isle. A stupid preview was playing so, naturally, I started fantasizing about wild sex (I seem to be doing that a lot lately).

Suddenly, I was awakened out of my reverie.

“Excuse me,” she said as she slid past me, rubbing her beautiful ass on my legs as she squeezed by. And of course I knew it was a beautiful ass, after all I was right in the middle of one of my fantasy moments. If she wasn’t with her male friend (husband?), I would have thought she did it on purpose. (*heavy sigh*) My sexual imagination getting the best of me again.
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