Chapter 5. Playing With A New Friend While Dresse free porn video

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While my friend Jim was pretty much my best buddy, I never tried to involve him in my panty play. I didn’t believe he would go for it, and I was afraid to suggest it to him for fear I would lose his friendship and become the object of his ridicule.

I did meet another boy my age, and I discovered he shared my passion for nylon. His name was Dale. He also had a mature woman fan the flames of his passion. It was his mother, but, as he told me, she merely facilitated his enjoyment of her lingerie; she did not participate as a sex partner.

I met Dale under the most unusual circumstances. It was summertime, and the weather was hot. Usually I wore as few clothes as I could, but always tried to find opportunities for wearing my panties.

One day no one was around to play, so I decided to go on an extended bike ride. I also decided to dress to enjoy the ride. I wore two pair of pink, full nylon briefs and a baggy pair of shorts. I would pedal hard to gain speed and then coast for as long as possible. While coasting, I would ride “no hands” and use my hands to hold the baggy legs of my shorts open so the warm breezes could go up my legs and across my nylon covered cock. The briefs were big and loose on me, so they would flutter in the breeze and give me an extra thrill.

As luck would have it, I was doing this in a park in front of a boy riding toward me on his bicycle. He couldn’t help but notice the bright pink colors showing up the legs of my shorts. As we passed, our eyes met and he smiled somewhat bashfully. At the moment I was mortified.

“Did he see my panties? Do I know him from anywhere? Will he tell everybody what he saw?” I was concerned and decided to get out of the park and on my way home as quickly as possible.

Before I could get very far, I heard someone behind me yelling for me to stop. “Hey k**. Wait a minute. I want to talk to you.” It was the boy who saw me wearing the panties under my shorts. I decided to talk to him instead of trying to speed away. He could always follow me, find out where I lived, and then make my life miserable without me even knowing it.

As he rode up he said, “Hey. Hi. Where you going? Got a minute?”

“Yea. I guess so. What do you want?”

“My name is Dale. What’s yours?”

“Bobbie. Why?”

“Listen Bobbie. Don’t be nervous. This may sound crazy, but I think we have something in common. You are wearing pink nylon panties, aren’t you?”

“What. Are you nuts? Why would I be wearing girl’s clothes?”

“Come on. You don’t have to lie about it. You know I saw you. I just want to talk to you for a couple of minutes and show you something. Let’s go over there in the field away from the path.”

So I followed him. What else could I do? We pushed our bikes through the field to some big trees that offered some privacy. To anyone watching, we looked like two boys doing some exploring in the woods. It turned out we did some exploring all right. Just not the kind anyone would expect.

We leaned our bikes against the trees and Dale said, “I want to show you something. He pulled up his tee shirt and reached in the waist of his pants. He grabbed the waist of what I assumed was his under pants. I expected white briefs. What I saw was white all right, but it was sleek and shiny. Just like my pink panties were sleek and shiny.

“Are you wearing panties too? Where did you get them? Why are you wearing them?” My excitement soon had me babbling like a fool.

“Slow down Bobbie. I will tell you what you want to know. I am just as excited as you to find someone who wears panties. They feel so good on me that I want to wear them all the time, but I was concerned I am queer. I thought no normal boy wears women’s panties. I just can’t seem to stop myself from wanting to wear them though.”

“I feel the same way Dale. I try not to wear them, and I hold out for a day or two, but then I have this incredible urge to wear them again.”

“Do you do anything while you are wearing them?”

“What do you mean?”

“You know. Do you play with yourself while you are wearing the panties?”

“No, of course not. What do you think I am? Queer or something? What about you?”

“No, I don’t think you are queer. But I do think you are a lot like me. I bet your pecker gets hard when sexy nylon lingerie of any kind touches it. I bet you jerk off with it, just like me. Like right now. I am getting so excited just talking to you about wearing panties and jerking off with them that I wish I was home right now so I could play with myself.”

Well Dale sure had me figured out. I certainly was experiencing those same feelings as him. My cock was straining against those lovely pink panties I was wearing. So as long as he was fessing up too, I figured I didn’t have anything to lose. I began to tell him about my life in panties. If you have read the previous chapters, you know what I told him.

While I was telling Dale my story, we both had our hands in our pockets, rubbing the fronts of our pants and the nylon panties under them over the heads of our excited cocks. We each knew what the other was doing, but we were still too cautious to do what we both wanted – that is to take down our pants and masturbate in our panties.

Then Dale told me about his panty experiences. He started out much like all of us panty lovers. Raging hormones, curiosity about the female body, glimpses of women partially dressed in sexy underwear, association of the nylon lingerie with sex, and easy access to that lingerie (in Dale’s case it belonged to his mom Joan) ultimately caused him to touch it.

All us panty boys seem to have a switch inside us. That first time we touch the nylon we become hooked for life. We become an addict that nobody talks about. Our addiction to nylon lingerie is every bit as strong as a junkie is to cocaine or an alcoholic is to booze. We just need to experience the pleasure of the nylon on our cock and our body.

Dale told me his mother caught him wearing her panties and slip. He can tell you in his story what happened, but the eventual outcome was that he was allowed to wear her lingerie.

When he told me that, I was so jealous. Imagine, being able to wear panties around the house whenever you want. Imagine being able to go to bed dressed in the luxury of nylon lingerie instead of old cotton pajamas. I was ready to ask Dale if his mother would adopt me.

But back to the park and my encounter with Dale. As Dale finished telling me about his start in panties, we both realized our cocks were hard and we were desperate to cum in our panties.

“Dale, do you live very far from here?” I asked.

“No, only about a 10 minute ride on our bicycles. Why do you ask?”

“Well, if you let me come to your house, I will show you my panties and what I do when I am wearing them. Do you want to do that?”

Oh, yes. That sounds like fun. I will show you mine too. If my mom is home, she might like to see you in your panties too.”

So Dale and I hurried to his house. As I rode there, all sorts of fantasies ran through my mind. Of course, I pulled up the legs of my shorts so the breeze blew across my rock hard cock. No reason to stop the activity that started this new adventure with Dale.

Dale looked across and saw what I was doing. My pink panties were so obvious that I might as well not even be wearing my shorts. He smiled and said he couldn’t wait to see me in nothing but those sexy pink beauties.

We soon arrived at his house. We went in the back door, and he called out to his mother. No answer, so we had the house to ourselves. Just as well, because I wasn’t too comfortable with the idea of showing my panties to his mother.

“Come on into my bedroom. We can have some privacy here. This used to be my mom’s bedroom. She still has her panties and slips in the dresser in here. When she realized how much I enjoyed wearing her things, she changed bedrooms with me. It’s really weird the way she lets me use her things, but it sure is convenient to slip in here.

Every night before I go to bed I take a clean slip and panties from the dresser and put them on. They have become my pajamas. Of course my cock starts to get hard right away. When I slide between the sheets, the feel of the nylon on my legs and chest is so nice that I can’t keep my hands off my nylon covered cock. The two layers of nylon feels great. Sometimes I even put on a second pair of panties. I just have to be careful not to make a mess in mom’s panties. I don’t want to make her mad by staining them.”

“Dale, you are really lucky. I love to sleep in nylon too, but I have to hide my panties and slip into them after everyone goes to sleep. Then I have to be careful the next morning so my mom doesn’t find me wearing them if she comes to wake me when I sleep in.

And what do I do with my cum? Sometimes I remember to take tissues or an old hanky to bed, and I cum in that. Sometimes I get so excited I can’t hold it long enough, and I cum in my panties. That feels the best, but then I have a mess to clean up later. Occasionally I miss both, and I get cum on my sheets.”

“Oh, you poor thing Bobbie. Too bad you don’t have a mom like mine. You’d be able to play anytime you want.

Like now, for instance. My cock has been hard since I saw you in your pink panties in the park. I can’t wait any longer. I need to get some relief.”

With that, Dale unzipped his pants and let them slowly slide down his legs to the floor. I watched as his sexy white panties came into view. They were very silky looking and had a little lace trim on the legs. God he looked sexy.

“Are those Joan’s panties,” I asked.

I thought he hadn’t heard me. His hands moved to his nylon cock as if they had a mind of his own. He rubbed his prick around inside the loose fitting briefs, clearly outlining his boy cock against the sheer white nylon.

“Of course they are’” he gasped. “Who else would they belong to? Now get out of your shorts. I want to see you in those pink panties. Hurry up! I’m almost ready to come.”

I quickly took off my shorts. My hands immediately went to my cock as well. The nylon felt so good on my cock. I just wanted to jerk off and come in my panties. I didn’t care that Dale was in the room watching me, and I am sure he didn’t care about me watching him.

“Bobbie, I like your panties. They look really hot. Oh, you are wearing two pair. I bet that feels great.”

“Yes, it does. But what are we going to do now?”

“I don’t know about you silly, but I am going to cum. I need more nylon, though.”

I watched as Dale tucked the elastic of his white nylon briefs under his balls. He pulled open a dresser drawer, reached in, and came out with a full nylon white slip. Then he climbed up on the bed, lay on his back, and pulled on his cock with a handful of that nylon slip.

That was all the invitation I needed. Watching Dale out of the corner of my eye, I rubbed my pink panties all over my cock. Wet spots appeared on the front. I continued rubbing, faster and faster. I was losing control.

I heard Dale moaning on the bed. I looked again and saw him throw the slip aside just as his cock started shooting cum up onto his chest. I lost it then. I just bent my knees to balance myself and shot my load of cum in my panties. What a delightful mess!

After a few minutes, I began to recover. Looking around, I realized what I had done. Actually, what we had done. I didn’t quite know how to feel. One part of me was embarrassed because I masturbated in front of another guy. The other part of me was hoping it was the start of a relationship that would see us do it again.

Dale put my mind at ease when he looked at me and laughed out loud. “God, that was wild. I love having an audience when I am playing in my panties. Until now it was just my mom, but watching you play with yourself while I was coming was too much. Will you do it again with me?”

“Do birds fly? Heck yes, Dale. I was worried you wouldn’t want to.”

“Good. Let’s me at the park again tomorrow at 10 o’clock. I am going to tell my mom about what we did today. She might want to meet you tomorrow.”

“Hey, that sounds great. Maybe I can find a way for you to meet my Aunt Florence too. I think the two of you would get along just fine. But I better start heading home now. My mom will wonder where I got to.”

I then started to take off my panties. “Wait, what are doing,” Dale asked.

“I can’t very well wear these home Dale. The front of both pair is wet and sticky with my cum. It will stain my shorts, and then mom will see.”

“Oh, yeah. Okay, I will tell you what we’ll do. I will loan you a pair of my mom’s panties to wear home. You can give them back to me tomorrow. Just don’t cum in them.”

So he opened another dresser drawer and took out a pair of white nylon panties, similar to the ones he was wearing. He handed them to me. As I took them, my cock sprang to life. All I could think of was the forbidden pleasure of wearing a strange woman’s lingerie. I pulled them up onto my ass and tucked my cock into the front. They felt delicious. Too bad I couldn’t ride home wearing just them.

I pulled on my shorts and walked to the door. Then I remembered I had left my pink panties on the floor in the bedroom. When I went back to the room I found Dale had already picked them up and was fingering the dry back panels.

“Feel good, don’t they? I want to take those with me and clean them, but I will bring an extra pair of clean ones for you to try on tomorrow if you want. All I really have are pink ones. Will that be OK?”

The expression on Dale’s face was all the answer I needed. Of course he wanted to wear a pair of my pink panties. So I put one pair of my cum-stained pink panties in each front pocket of my shorts and headed for the door. I definitely would meet him (and maybe his mom) tomorrow.

Outside I got on my bike and started pedaling home, again enjoying the thing that led to this encounter – feeling the breeze up my pants leg and across my nylon-covered cock.

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Sorry for the part 1 guys I accidentally press post and I din know how to edit but anyways here's the part two hope you like it. Jake said he was really sorry for what happen. I was a bit mad because of he said that. I thought he liked me so I ask him "Jake, do you really like me or you just made me feel better about what happened with nick? Jake drove and no words came out of his mouth not even a nodd. I was dissappointed I thought to myself I will never ever do this stupid things I did to...

4 years ago
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Me and my bestfriend Jake part 2

Sorry for the part 1 guys I accidentally press post and I din know how to edit but anyways here's the part two hope you like it. Jake said he was really sorry for what happen. I was a bit mad because of he said that. I thought he liked me so I ask him "Jake, do you really like me or you just made me feel better about what happened with nick? Jake drove and no words came out of his mouth not even a nodd. I was dissappointed I thought to myself I will never ever do this stupid things I did to...

4 years ago
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Friend to Crush to Friendzoned Cuck 2

After we woke up from our nap we only briefly talked about what happened. I again admitted that I loved her, and even though what happened was hot, I wasn't sure if I'd want something like that again because of my feelings for her. She said she understood and we would keep it a secret. It was to be buried between us, never to be talked about again.Things seemed to have gone back to normal. We didn't talk to much during the week, then she texted me on Friday. She asked me if I wanted to go to a...

4 years ago
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Amazing Friendship Anniversary Moments With A Friend 8211 A Lovely One

Hello everyone. Here Raj again from Bhubaneswar presenting my first ever story. Thank you all for the feedbacks received for my previous story. You may please contact me for feedback of this story too at Ladies, aunties and unsatisfied women are most welcome. You people can drop a mail to me if you want a secret relationship or some fun. Your secrecy is my guarantee. Now coming to the story. Who don’t know me previously, for them; I am Raj, from Bhubaneswar, Odisha. Well-built with gym touch....

3 years ago
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From friend to crush to friendzoned cuck

I've known Sarah for years and we hit it off immediately. I always thought she was attractive, with her long legs, her dark hair, her beautiful thick lips. But I didn't have romantic feelings for her right away, it was something that slowly grew as we spent more time together. One night we were drunk at her place. We flirted a lot, and I thought it was time for me to finally make my move. I told her how I felt, but she gently let me down. She said she couldn't ruin our friendship. She loved me,...

2 years ago
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Girlfriend Flirts with Boyfriends Father

I was living at home right after I graduated from college and I was dating this girl Brittany at the time.  She was a little wild though and I had a hard time dealing with her. This one time, my mom was out of town visiting her sister and Brittany came over to visit and have some beers.  It was a hot summer day and we were drinking by the pool and my dad was in his lawn chair, reading the paper under a shady tree nearby.“It’s so nice out, I want to go swimming,” said Brittany stretching...

Cuckold
3 years ago
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Fucking My Girlfriend While Her Friend Watches 8211 Part 1

Hi everyone! This is my first story here. It might be a bit lengthy but it is definitely worth reading. I am Aman, 23 years old, 6 feet tall, muscular build and with a shaft of 6″. This is my story of indulging in an extremely erotic threesome with my beautiful girlfriend and her even more beautiful friend. So without any further delay, let us start the story. I and my girlfriend are internees at a medical college in Kolkata. We first met during the first lecture ever attended by us in the...

2 years ago
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My girlfriends best friend1

The previous day she had been wearing a short skirt and platform heels the entire day, when I had met her, and nearly every subject we spoke on she connected with sex somehow. My girl knew from the way I had been watching her friend's legs stroll down the street in front of us that I was probably going to try and fuck her. She also knew that if her old friend said no that it would only be rougher for her. She had thought about warning Karen not to say no, but had decided her slutty friend...

2 years ago
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From friend to crush to friendzoned cuck part 9

A little later in the week I talked to Rachel some more. She told me Eric would be into the idea of me being there while they fucked and them treating me kind of like their cuck. We set up a time for Saturday. They had plans for the night, so they wanted to do something early in the day, which was fine with me.Although I never had the feelings for Rachel like I did for Sarah, Rachel is very attractive. A pretty blonde girl, busty, curvy. She's soft in the right places. Unlike Sarah, I've...

4 years ago
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Caught in my girlfriends lingerie by her friends

My girlfriend lives alone, so whenever I am at her house by myself, while she's out clubbing or working, I always take the opportunity to go through all of her sexy clothes and lingerie and dress up like the slut that I crave to be.I undressed and put on a pair of white fishnet stockings, a black thong, mini skirt, black and white see through top and a sexy pair of silver high heels. I set my camera up at the end of the bed and set it to record myself in various poses. After a while doing this,...

Crossdressing
1 year ago
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The United Kingdom of Zoo A fake BBC documentary seriesS14 E13 Ruby Suddick 25 from Newcastle

We start this week’s show with establishing shots of a Geordie-land’s infamous night-life. Along the Quayside, teaming with young bodies as the youth of the Toon move from pub to pub, barely wearing enough to protect them from the cold northern wind. Then we’re around the corner on a street with four story buildings on either side of a wide street, with plenty of pedestrian space infront of multiple pubs and clubs. Everyone looking very relieved that the lockdown is over and the party has...

2 years ago
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Tricked by his BestFriends Girlfriend Gay

"Dude, I need your help, and it's gonna sound crazy, okay?" Caleb immediately said as he opened his front door to let his friend in.His best friend Adam has just arrived after receiving a frantic phone call from Caleb only twenty minutes earlier explaining that it was an absolute emergency and that he needed him to come over immediately.Caleb lived not too far away on the other side of the campus and so he quickly threw on some runners, his jogging shorts and a gray sweater and headed over to...

3 years ago
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My Girlfriends Girlfriend

My Girlfriend's Girl Friend Although this is fictional, many parts of this story actually happened. You, the reader can decide for yourself which are real and which are entirely a lifetime crossdresser's vivid imaginations. My name is Don. This story takes place in the late 60's when everyone had a little different or new view of their sexuality. From the time I was able to masturbate, I was in my mother's lingerie drawer trying on her silky panties and hose. I was probably 12...

2 years ago
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Constructing New Friendships Part 1

The following is fictional. Names, and locations have been made up and are not meant to depict real people, living or deceased. These stories also depict dangerous, unprotected sexual encounters. In this day and age of killer STDs, please be careful and wear protection! Only YOU can keep yourself healthy.This is an adults only story. If you are u******e in the community you live in, please do not go any further. Thank you and happy reading!Note: This is one of the first stories I wrote for my...

4 years ago
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Friend to crush to friendzoned cuck part 8

It didn't take much to turn me on. Before I knew it, I was jerking off again for the third time that day. I was looking at a pic of Sarah and Rachel together. In my state of horniness, I texted Sarah."So I thought about it, I'm okay with you telling Rachel about me being your cuck," I typed.What I got back was a much longer response than I expected."Are you sure? I don't want to make you feel obligated. I really care about you and I don't want to ruin our friendship with this. I want to tell...

3 years ago
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Playing Footsie with friends wife

This is a true story. As the title implies, it involves me playing footsie with one of my closest friend's wife and he doesn’t know about it! No, I'm not cheating on my friend with his wife, nor is there anything romantic going on on the side. We just play footsie and that’s it. No names will be mentioned, other than the fact that my friend’s wife is a petit South East Asian, who is shorter than me and I'm 5'3, and hence, has petit, cute feet.This all started about five or so years ago. I have...

3 years ago
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A construction superintendant has a threesome wwith a fourteen year old girl and her boyfriend

As a construction supervisor I meet all sorts of subcontractors. Working on a Saturday is not uncommon and often the subs bring their teenage sons along to learn the trade. This was the case when I met Dillon. Now I am a straight male but even I have to admit this boy was cute. Small boned, brown wavy hair to his shoulders, blue eyes and an engaging smile. At lunch time Dillon found me in the construction trailer and asked if he could talk to me. “Sure,” I said pushing a chair towards him. He...

3 years ago
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The Newlins Marcie and MarkChapter 13 Stunning News for Mark

Mark was still mortified the following day and called in sick rather than face his boss, Ezra DeZam. But DeZam surprised him, and came by his motel room to see how he was and to impart some important information to him. “Listen Mark, here in Monroe, some of us play it fast and loose. We have good reason for it. Other folks have tried to fit in here ... this climate sucks. We get torrential rain followed by floods and the humidity and heat are enough to drive you crazy. Seemed like everyone...

3 years ago
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My Girlfriends Gum A Witchy Girlfriend

My Girlfriend's Gum (A Witchy Girlfriend) By: Boredsitting This story is heavily influenced by the story A Force Of Habit by Jessica Drew. I read the story a long time ago, and it is still one of my faves. There's also some other influences in here, as well. I just hope that it is as good a read as hers. Also, I tried to change the story about midway through to avoid copying her directly. The first half is a tribute to A Force Of Habit, but the rest needed to be my own. This...

1 year ago
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Girlfriend Her Bestfriend First Time

I sat down and turned on the movie as the two girls got the food ready. It was still early in the night and we had nothing really planed. Sara, my girlfriend, sat next to me and handed me dish of food. Amanda, Sara’s best friend, sat on the couch across from us. We had a few beers each as we ate and watched the movie. Time moved on and the events of the night took an unexpected twist. Before we continue let me describe Sara. Slightly darker skin, about 5’5 with shoulder length black hair. Her...

Lesbian
4 years ago
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A New Gurlfriend

A New Gurlfriend by Paul1954 Discovery - May 14th, 1999 William Alistair Burns slammed the door shut, threw down his wet umbrella in the corner of the hallway, and started to remove his wet overcoat as he examined the drawn, and pale looking face that stared back at him in the mirror. He had just been through another piss awful day at the office and had arrived home late once again feeling mentally drained and physically exhausted, and he was really looking forward to winding...

2 years ago
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Meeting my ExGirlfriends New Boyfriend

Not long after I got out of the service, I met Trish at a house party. She was a hot little brunette with a great body and we hit it off right away. After a few months of dating we ended up moving in together and she was a great lover...with one little quirk. She always wanted me to wear a pair of her panties while we were having sex. I readily obliged because she was so good on her back and also gave the best blow job I've ever had. I got used to wearing her underwear and have to admit that I...

Crossdressing
1 year ago
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Friend to crush to friendzoned cuck part 7

When I woke up I helped clean Rachel's a little bit so the whole place wasn't a complete mess. Eventually Sarah and Mark came out of the room. It was awkward with other people there, and no one really said anything. I felt like everyone kinda knew I was a cuck, even though Sarah and I weren't together. I knew I had been in love with her, but she just fucked one of my friends. My two best friends were fucking each other and I was stuck masturbating.Eventually Sarah asked me to drive her home....

1 year ago
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My Friend My Friends Mother Me Have The Time Of Our Life

I waited outside the door waiting for her to open the door. Soon I heard footsteps and the door opened. It was her mother. For a moment I was awestruck. This was the first time I had seen her mother and she was beautiful. She must have been around 40 but she had a very firm pair of breast. I could see that she was not wearing a bra or anything. So her tits were just bouncing around when she walked. I could even see her nipples. Suddenly I had an urge to touch them, but I contained my self and...

First Time
3 years ago
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Reese Witherspoon dommed

any of the actresses mentioned below. This story is written down for enjoyment purposes only. Reese witherspoon woke up with a headache. She didn't know where she was. All she could feel that she was blindfolded. Not only that, she was tied to the bed with duct tape, unable to move her hands and legs. She also noticed that she was nude. A duct tape covered her mouth so that she shouldn't shout. All she remembered was going to a producer's home for some script reading of a film they were...

4 years ago
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First Time With Crossdressers

For once, I actually decided to look at some of the other categories on the streaming sites I'd visit. So many things came up under fetish. Some of it I don't get but to each their own. A BBW was mixed in with the fetish and as I had expected before hand, it wasn't my cup of tea. Several videos had girls dominating guys in leather or latex outfits. I liked how tight they were, showing off every curve of their body, leaving little to the imagination. Upon thought, I had never been...

2 years ago
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Chronicles With Sexy Crossdressers

My email id is Do not forget to let me know how this sex story was. Who knows, we might get even lucky if everything goes well ;) Clean shaved men inside female clothes (or people who are known by the name crossdressers) are my new found favorites. Believe me, I always make it a point to taste every bit of them with passion and fire. My hands and tongue never leave an inch of their body. Hairless, like women and the ‘EXTRA’ jackpot called ‘COCK’, is simply divine. This is a story of how a...

Gay Male
1 year ago
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Constructing New Friendships Part 2

The following is fictional. Names, and locations have been made up and are not meant to depict real people, living or deceased. These stories also depict dangerous, unprotected sexual encounters. In this day and age of killer STDs, please be careful and wear protection! Only YOU can keep yourself healthy.This is an adults only story. If you are u******e in the community you live in, please do not go any further. Thank you and happy reading!Note: This is one of the first stories I wrote for my...

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