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At School and Work

High-Heeled Slut

On television, a guy that works in a womenís shoe store is supposed to be the lowest form of life. While the pay is not the best in the world, I enjoy the fringe benefits that were associated with my summer job. I enjoyed how my patrons would flirt with me by flashing me a peek at the crotch of their panties, or even some that were willing to give me a peek of hair pie.

One afternoon, the mother of a classmate came by. She said she wanted a pair of boots. I told her that we had a good selection of designer boots and off-brand boots. I told her how the biggest issue in her decision was what type of response she wanted to get from the guys. She smiled and said she would go with whatever I thought might be best. I went to the back room and got out a pair of Steve Madden boots with stiletto three-and-a-half-inch heels. I told her that these were the type that were worn with either a suede or wool skirt, and would cause every guy she walked by to get an erection.

I also told her that I would be willing to give her a personal discount at the cost of my commission of the sale. She smiled and said she didnít want me to do that. She didnít just buy one pair of boots; she picked up four pairs (in black, camel, white and red). This caused the store manager to offer her several pairs of matching stockings. The manager also didnít have a problem when she asked if I could help her carry the boxes to her car. He was all smiles and said for me to take the remainder of the afternoon off.

She drove me to her nearby condo, where she slipped out of the shoes. Then she asked me which pair I wanted her to try on first. I picked the white pair, and with a smile, she slipped them on and began to walk around the room as if she was a high-fashion model. When I told her that I thought she looked great, she said she was hoping that I would be willing to show something else. It was my time to smile, as I knew what she wanted and was more than willing to comply.

I undid my belt and, in one motion, dropped my slacks and briefs to the ground and revealed to her my erection. And while she looked great in the boots, it was the fact that I found her sexually appealing that got my cock hard. She licked her lips and asked if that was for her. She didnít wait for me to answer as she dropped to her knees and began to give me head. She was barely able to wrap her lips around the head of my cock, but did her best and even attempted to deep-throat me.

She sucked on my cock for several minutes before getting up and taking off her clothes. Once she was nude, with the exception of the white high-heel stiletto boots, she sat on the edge of a table and asked if I would be interested in returning the favor. I immediately dropped to my knees and began licking at her pussy, and from looking at the blondish hair, I was able to conclude that she was a natural blonde. I licked and finger-fucked her to several orgasms before fucking her.

She was much more vocal than some of the girls I had sex with from school, as she moan and gasped. She also screamed out obscenities of what I was doing to her with that giant cock of mine. I continued to fuck her while standing up, until her knees got weak. I then moved her to the living room sofa where I licked her pussy from behind while finger-fucking her bunghole before penetrating her pussy doggie-style.

She enjoyed making love to me and finished with me experiencing an orgasm while she was on top. We rested, with her still impaled on my erection, and she didnít make any effort to do anything until my cock began to shrink and slipped out of her pussy.

After showering together, I got dressed in preparation of leaving. She thanked me for a wonderful time and said she would be back in a couple of weeks. She also slipped $200 in my pocket as a tip for all I had done.


Party on the Playground

Thereís this very sexy 43-year-old woman I work with at a grade school, and she has flirted with me for the past year. We would eat lunch together, talk about dating, relationships, work and such. One day on the playground, I mentioned how we should sneak off into the woods for a while. She said it sounded like a good idea, but not here.

Some time later, she called me up and our conversation turned to sex. I asked her why she cared so much about my sex life, and she said it was because she didnít have one. She asked if I would talk dirty to her. I told her to lie on the bed and I described how Iíd fantasized about her for months and wanted to fuck her. She even told me about how she would stare at my cock during recess. I could hear her moaning as I talked about eating her out, fucking her doggie style and 69ing her. Later, I asked her if she came and she smiled. She didnít say yes, but when I asked her if I made her wet, she only smiled more.

Since then, weíve gotten together to watch porn and I write her sex-stories. She gives better head than any one of the under-30 girls. Most times, I just have to pull out my cock and sheíll suck me and swallow it. Itís been great! She especially loves to have me fuck her in the ass while she uses her dildo. Man, I love MILFs!
 

College Times

I am a senior in college. I go to a university in the Northeastern part of the U.S. I am a communications major. In my college for my major, there is this secretary that I have gotten to know from all of my time spent in that building. Her name is Vicki. She is probably in her late 50s. She has short grayish-black hair and is fairly tall. She has a nice body, not overly skinny, but plump with a nice butt. She definitely turns me on. As a college student, my hormones are raging, and at we all have fantasies of fucking older women. She is mine. I always think about Vicki sexually. I have dreamed of fucking her.

Anyways, Vicki was throwing an end of the semester party at her house for all of the new communications graduates that she was close to, as well as faculty members. This was my only chance to ever show Vicki the way I felt. So, when I was invited, I purposely got to her house two hours earlier, claiming I forgot what time it started. Vicki said, "No problem, I'm glad you're here." After helping her set up for a little bit, I went to the bathroom to execute my plan. I left the door unlocked and began to strip. I was all naked and started stroking my cock thinking of Vicki. Then I started moaning her name out loud, so as to get her attention. Vicki heard something, and she yelled out, "Are you okay?" Then I heard her walk towards the bathroom. She called out but I didn't respond. Then she opened the door and saw me jacking off to her. She sort of blushed and looked awkward. I explained everything to her, what my intentions were: to fuck her because I think she is amazing, I have always liked her, etc. Then I apologized and told her I wouldn't tell what had happened and was about to leave, when she said that it wasn't a problem and that she was flattered.

Then came something I thought I would never hear: "You know, I've always liked you too. I wouldn't mind doing it with you." I asked her if she was serious, and she said yes, but I couldn't tell anyone. As long as she did the same, I So we went into the bedroom, I was stark naked and jumped on the bed. She stripped into her bra and panties. I couldn't believe this. I was about to fuck my deparment secretary. My dick stood up and was rock hard, all 7 inches of it. Vicki then took off her bra and underwear. I saw the most hairy pussy in my life. I loved it, that is a huge turn on for me. She got on the bed with me, and I asked her to give me head. She said, "I haven't done this in a long time, so bear with me." I didn't care, I was turned on from the start. Vicki grabbed my hard cock with her soft hands and stroked my shaft. Some precum formed and then she buried her mouth on it. Immediately I quivered, as her mouth was going up and down on my cock. After 30 seconds, I was about to come but she stopped so that I could save it.

Then Vicki got on her back. I asked, "Can I eat your pussy?" Vicki said yes. I told her that I loved hairy bushes, it was such a turn on to me. Her pubes nearly covered her belly button. I put my mouth on her mound and started licking her pubes and opening her pussy lips, and started moving my tongue around it. I could tell she liked this because she started to moan. I separated her clit with my hands and then put my finger in her pussy and moved it in and out. After playing with her vagina for about two minutes, from eating it to probing it, Vicki started to emit some groans.

Then I was on my back, and she got on top of me. Her pussy was so loose, after squeezing out a couple of kids some twenty years ago. She positioned her pussy on my cock and sat down. Oh my God, it felt good. And just the sight of it got me going, my college secretary, an older woman, was fucking me. Vicki started riding me. It felt so amazing. She threw her head back and started moaning, like she was a seasoned vet. I started talking dirty because I couldn't hold back: "Oh my God Vicki, you are so amazing, yeah baby, ride that cock. Ride it faster God damn it!!!" Vicki looked like she was enjoying it, making facial expressions that bordered on pain and enjoyment, she was also breathing very fast.

I quickly turned her over on her back, and fucked her the usual missionary style. I was pounding her pussy hard with my cock, turning myself on by looking at my dick go in and out of her hairy pussy. I was on the verge of exploding, I said to Vicki: "Vicki, I'm gonna cum...you want me to pull out?" Then she said something that was a dream come true. "No, I want you to cum inside me, I can't get pregnant at my age." I lost it then. I looked down at her pussy one last time, then up at her contorted face, realizing that I was fucking a faculty member at my university. Then off I went. "Oh God Vicki, I'm cumming, I'm cumming!!!....ahhhhhhhhhhhhh" I let out the scream of my life as I deposited my sperm inside of Vicki's womb. I shot about three jets of cum into her and the final few drops onto her pussy hair because I think that is so nasty. I rubbed it all around her pubes, and my cock emitted a little more cum because her pubes felt so good. I asked her, "Bet you never thought what I wanted to do today at this party, huh?" Vicki said no, but that she definitely enjoyed it. I told her it was the best feeling, like now, this is all a dream of mine. The beginning is true, I am in love with Vicki sexually. I want to fuck her badly, even though it is highly improbable. But, I can always dream. And my dream has been this story

Anal Sex | Neighbor | School and Work | Mother-in-Law | Step-Mom | Friend's Mom | Masturbation

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