From Frat Boy to Sissy Boi Pt. 1 Phone Sex

His name was Chad. Of course it was. Aren’t these frat dudes all named Chad, or Tad, or Brad? He was about 6’2″, blonde blue-eyed All American man’s man. Handsome, masculine, and dumb. Oh so dumb, but very sweet. I was tutoring him in English, and we had been working together for a couple of semesters, so we had gotten to know each other well. We hadn’t hooked up or anything, which was pretty surprising for a whore like myself.

I found out his secret when he opened the wrong tab on his laptop one tutoring session. It was a video clip of a hot guy in women’s panties going down on some huge dude. Chad shut the laptop, embarrassed, but I poked him in the ribs and asked him to dish. He shyly admitted that he got turned on by wearing ladies’ panties. Not only that, he added, but he wanted to be made to do things like the guy in the clip, to suck a dude’s cock, preferably in front of other people.

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Open House Open Legs Phone Sex

The open house was nearly over, and I had been walking around town. On a whim, I decided to check out the beautiful contemporary home just for fun (not like I have the cash for a home lol)

The real estate agent was a tall, blond older woman, quite attractive with big tits like mine. She greeted me warmly, and gave me a personal tour of the gorgeous new house. Our voices echoed in the empty grand room as we chatted about the house and the neighborhood. The way the agent was smiling at me was reminiscent of the looks my lovers give me when they want to fuck my brains out. Or maybe I was projecting my lust onto her, and was just imagining it.

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First Anal Phone Sex

mmmmm anal sex, so fucking hot, I love it! My first anal experience was unplanned. It was a little while after I had lost my virginity to my professor, and I was dating another older guy. I was on my hands and knees, taking his cock in my pussy. Something came over me, and I just said “I want you in my ass right now”. My boyfriend, in the midst of pumping away at my cunt, asked if I was sure, and I gasped out yes. He withdrew his cock from my pussy, then spread my ass cheeks with his hands.

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The Boutique Salesgirl Phone Sex Pt. 2

 

Melinda, the hot Black salesgirl with the thick gorgeous body, had just kissed me in the dressing room of her boutique. Her hands gripped my ass cheeks, as I returned her kiss. With her heels on and tall stature, I felt like I was making out with the most beautiful Amazon. She pushed me against the wall and, her lips still on mine, ran her hands up and down my voluptuous body. As she kissed and licked my neck, she hiked up my dress, revealing my hairy pussy clad in baby blue bikini panties.

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The Boutique Salesgirl Phone Sex Pt. 1

I’d mentioned before that I had gained some weight since starting grad school. Even with biking to campus every day, I had a few more pounds on me than a few months ago, and I could feel it in certain articles of clothing. So, I decided to get some new outfits for my increasingly voluptuous body.

My friend had told me about a chic little boutique that offered quality pieces in my size (I was starting to creep into the plus size category). The shop was staffed by thick girls of all shapes and sizes, all dressed to the nines and looking like hot femme goddesses.

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For the Love of the Quickie Phone Sex

 

Sometimes, there’s nothing like a quickie. I’m so busy with school and work, that at times, I have no more than a few minutes for fucking. But, I’ve learned to appreciate the quickie. Good sex is good sex, no matter the duration.

My latest quickie was earlier tonight. I was getting ready for work when I got the text – “wyd”. It was my roommate’s friend, whom I’d known for a few months, and we’d finally gotten around to fucking. He was a busy guy, so our encounters were brief, but hot. My pussy pulsed as I texted back–“getting ready for work. Wanna cum over?” He texted back “omw” and I ran and brushed my teeth.

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Snowballing My Lover Phone Sex

 

My 24-year old lover and I were laying naked in my bed and making out, our hands caressing each other’s bare skin. I loved being with him–he was probably the closest I had to a boyfriend. Intimacy with him was so easy, and he was such a great fuck. I was smelling his skin and kissing my way down his neck and tummy as he caressed my hair and massaged my neck.

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Naughty Elf on the Shelf Phone Sex

Holiday time, and I was caring for the little one of the hot single father who lived downstairs. He had to work a late shift, so he asked for my help since his regular sitter was sick. His apartment was decked out for the holidays, complete with Christmas tree and that ubiquitous elf on the shelf. The dad said it was cool if I had someone over, so I invited one of my male study buddies to do work on a grad school project.

My study buddy and I did a little bit of work, but soon ended up naked and fucking on the dad’s living room couch. The little one was asleep and content, so I only felt a little guilty as my pussy got a pounding.

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Mistletoe Ho Phone Sex

My date was taking me to the holiday party for his work. We met at my first library job, while he was checking out books. I had just begun to love my ample body, and was showing off my tits and booty in a festive (and tight) red dress. I quickly realized I was dressed totally against the vibe of the party. It was very casual, more ironically ugly Christmas sweaters than clubwear, like my dumb ass was decked out in

Oh well, what the fuck, I thought. I knew I looked hot in the dress. My date had already given his approval with a “Damn, girl!” and a quickie fuck against the wall before we left for the party. so I know he was ok with it. He brought me around and introduced to his coworkers and boss. I got a couple of dirty looks from a couple of the other women, but fuck that! Sister, you wish you looked this good.

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Cuntry Boy Phone Sex

 

He was a farmer, which I found so hot. Met him at the farmer’s market. I found his number in my box of strawberries–smooth move. With his beard and overalls, he reminded me of a hot Amish hipster. I called him, and he invited me for lunch at his farm. I hoped lunch also meant dessert, in the form of his cock.

As he led me around the property, showing me the paddock, the adorable goats, and the expansive land, I was barely listening. I was mesmerized by his tan, muscular arms and the way his jeans hugged his great ass. As promised, we had lunch, and he fed me strawberries after. The sweet juices ran down my chin, and he wiped them away, and we laughed. He gazed deeply into my eyes, and said he bet I tasted as sweet as the berries. I said he needed to find out, and leaned over and kissed him. He grabbed my face and kissed me deeply, and then licked my lips. Sweet, just like I thought, he said. I giggled and said my other juices are just as sweet. He grabbed my hand and pulled me toward the barn.

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