Old Friend, New Relationship free porn video

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Note: ——I am NOT the author!so plz Don't ask me about part two,am simply sharing

this lovely story with all of you because I have not seen it on here
I met Karen in my divorce support group while I was dealing with my second divorce

and she was trying to cope with her first. About the only thing that we had in common

was that both our spouses had cheated with good friends of ours. She was a couple

years older and very attractive. I remember that she always dressed so well for our

group meetings. We both attended regularly for almost a year, in which time several of

us formed a sort of loose union. Among those in our circle of friends was Jane,

another gal about our age who was trying to overcome abuse at the hands of her ex-

husband. She was pretty strong, though, and in short order was back in control so it

seemed to me.

But one by one, members dropped away as new people joined the group and created

their own synergy. I never lost track of Karen, though. We would get together for dinner

occasionally, exchange greeting cards, and just talk on the phone every once in a

while. I never asked her about her love life and she never inquired about mine. She

knew that I moved from one relationship to another while I never detected that she

even dated.

The whole time, unbeknownst to a girlfriend I had at the time, I was dabbling in my

hobby. I was a closet crossdresser, and without someone living with me fulltime, I had

ample closet space. But I always yearned for that relationship in which I could be open

about my desires and even indulge in my deepest fantasies of feminization. I was

willing to settle for just a taste of things, but I never thought that I could trust any of my

girlfriends.

I’m not sure when my desire to share my secret with someone started, but it never

went away. Over the years, it would come and go, always coming back stronger than

before. And increasingly, I thought that Karen was probably just the right person. She

didn’t know anyone that I knew and her integrity was beyond reproach. Every time I

called her and hung up without telling her, I felt like I’d let an opportunity slip by. I

rationalized my silence by convincing myself that the topic was something best

discussed in person. I needed to make another date with her, and I did.

I can’t remember ever being so nervous as I was that day. As soon as the date was

made, in honor of what I hoped to share, I decided I’d be all dressed up—at least

underneath. If I didn’t get up the nerve to tell her (a very distinct possibility), I would at

least have the pleasure of going out feeling all feminine underneath my male clothes. I

shaved. I lotioned. I painted my toenails. I selected a black, heavy garter belt, black

panties and a pair of stockings that I’d been saving for Lord knows what. Before I set

off, I opened a bottle of wine and had a large glass of the liquid courage.

After a pleasant dinner at a local Italian restaurant (and some more wine), we went

back to her house for a little more conversation and, of course, some more wine. You

might think that this is where the story takes a decidedly more interesting turn (as I’d

hoped), but I was made to wait. When things were just right, I dropped the bomb. Not

surprisingly, she handled the news well, saying basically that she respected whatever

people did in the privacy of their own homes and that she would expect anyone to do

the same for her. It was that latter comment that should have been a signal. Instead, I

said my goodbyes and drove home, wondering about what might have been.

A couple days later, she called me back and told me that she had been thinking a lot

about what I’d told her and that, the more she thought about it, the more it intrigued her.

She said that if I was interested, she would like to see me fully dressed sometime.

When she asked about what kind of outerwear I had, I told her that all I owned was a

black leather skirt and a black blouse. I was more than a little surprised when she

specified that my outfit had to be some combination of pink and white: shoes, hose,

skirt, blouse and underthings. I thought that this was a rather odd request from

someone new to my scene and secret, but I also felt like it was kind of an order that I

was more than happy to try to comply with. We made a date for the following Saturday

and I wasted no time in making an appointment with a local gal who specializes in

makeovers for guys like me and then set about accumulating the new things that I

would need. The short time frame meant that I couldn’t shop while hiding behind the

anonymity of the internet. I had to go out and find my outfit. With some considerable

discomfort, I ended up with a sheer white blouse, a pink miniskirt, and some pink,

patent pumps with five inch heels, naturally. And of course I had the foundation

garments. I opted for a very strict white corset with garters, white panties and white

back-seemed stockings.

That Saturday I could barely contain my nerves as I set about preparing. After another

close shave and application of false toenails (French tips), I set off to Judy’s place

toting my outfit, false eyelashes & nails, brunette wig, jewelry, and purse along with

anything that I thought I might need. At Karen’s request, I threw in a nightie. I hardly

remember Judy’s makeover, but by the time I left trailing a lovely feminine scent

courtesy of my makeup artist, I felt truly transformed for the first time.

I arrived at Karen’s exactly when she told me to and rang her doorbell. I guess I thought

I’d be invited in and we would sit and sip wine while I told her about my history with

women’s clothing. The best I could hope for was to show a curious Karen how I was

dressed at which point she might be turned on and end up playing with me like a new

toy. So I was surprised when she answered the door almost immediately. I couldn’t tell

what she was wearing underneath her long leather coat, but there was something

subtly different about her. She had a more imperial demeanor and, unless I missed my

guess, she was more heavily made up than for our recent dinner. She brushed past

me and indicated that I should join her in her car. When I asked where we were going,

expressing that I didn’t think I was ready for a public appearance, she dismissed my

objections with a wave of her hand toward the passenger’s side of the car. I obediently

and nervously climbed in beside her. Once we got going, she said that she thought it

was time I took my hobby to the next level and then she remained silent for the rest of

the half hour trip.

Our first stop was a small jewelry store in a strip mall near her house. Against her

objections, I dutifully followed her into the store. When the young man working the

counter asked how he might help us, she told him that we were there for an ear-

piercing. He invited her to sit at a counter towards the back of the store set up for just

such a procedure, and she, of course, indicated to him that I was the one who'd be

getting his ears pierced. Once atop the stool, the now nervous young man (since he'd

discerned my rue gender) brought out a series of stud-style earrings that would be my

first. "Those just won't do", said Karen. "We'd like some large hoops for our girl here".

He tried to explain that saftey policy dictates use of studs for a "break-in" period, but

the wave of a $20 bill by Karen made him forget all about "procedure". In no time, and

with scant little pain, I was walking out of the store sporting a large set of hoops above

which there was an additional set of studs "just for good measure" according to Karen.

We resumed our drive and soon pulled up in front of a modest house in a nearby town.

As we walked up the front sidewalk, the front door opened even before we reached

the door. Clearly we were expected. We were greeted by a tall, broad-shouldered,

heavily made-up woman wearing a skimpy maids’ outfit comprised of a pink satin

dress, pink seemed stockings, white high heeled pumps, and topped by a frilly lace

cap perched atop long, cascading red hair. Despite the fact that her breasts were

undoubtedly hers, it seemed apparent that she had not been born with them. I knew at

once that my hostess had spent at least part of her life as a man. I was instantly

excited.

We were shown into the back of the house where I was surprised to be reunited with

Jane, she of the old divorce support group days. Her face was about all that I

recognized. The rest was made more difficult by the fact that her now more statuesque

figure had been poured into a red latex dress that ended far enough above her knees

to show off the lace tops of her black stockings. Normally I would have remarked on

how much taller she was than I remember but five inch heels will do that for a

woman—or a man for that matter. She greeted me with a European kiss-kiss and said

that I looked great. I thanked her for the compliment at about the same time that the

maid returned with three cosmopolitans which she deftly served in spite of her own

towering heels.

Jane asked, more like demanded, that I sit oppositee her on the couch and catch her

up on how I came to be sitting in her living room so dressed. Over the next two hours I

gave her the unabridged version starting with my compulsion to set my hair in my

mother’s rollers when I was home alone in high school and proceeding up through my

decision to come clean with Karen who sat transfixed throughout the story. At the

completion, Jane said that she understood my desires perhaps better than I did myself

and that I’d finally found a home. If I was interested, she believed that, with the help of

Karen and Ricki their maid, I might find fulfillment. I was encouraged to consider it and,

if I was game, we could start that night. Without thinking too much, I managed to

squeak out that I was very interested. With that, Jane got up and said that I needed to

see more of the house.

With some difficulty, I made it down the stairs to the basement behind Jane and Karen,

with Ricki dutifully bringing up the rear. We went down a short hallway that led to a door

that necessitated two keys to unlock. Prior to entering, Jane explained that there were

certain rules that applied to this room, the first being that anyone who owned or had

ever owned a penis was required to wear a posture collar. The second, and most

imporatnt rule according to Jane, was that everything that happened inside the room

was of a voluntary nature--nothing would be forced upon anyone. It was made clear to

me that my participation in whatever happened in this room would be within my

personal bounds. I quickly agreed to the terms, the excitment mounting in my stomach

and my little pussy. After having established a safe word that would put an immediate

stop to any of the proceedings that I deemed too much, Ricki reappeared at once with

a rather severe pink leather posture collar. Karen held up my hair all around as Jane

fitted the collar around my neck and buckled it into place.

I smoothed my skirt to dissipate my nervous energy, an act that elicited chuckles from

the other three. "I think he's going to be right at home here, Karen", mused Jane as I

was led into a virtual feminization playground. The first thing I noticed was a

gynecological exam table. Surrounding equipment made me think that real live

gynecology had been performed there and later that year, I would find out how true that

supposition was. All sorts of equipment that I’d previously only seen in trade

publications soon came into view. But the thing that got my fullest attention was a

beauty salon station complete with a make-up counter, shampoo bowl and hood dryer,

and manicure and pedicure stations all arrayed around a majestic fuchsia-colored

chair. Beyond that, mostly out of my comprehending, the walls were covered with a

variety of feminine accroutrement including high heels, wigs, dresses, purses, hats

and even a small collection of wedding dresses. It was a massive room tastefullt

decorated yet crammed full of the essence of feminity. Of all of it, that beauty salon

chair held my gaze the most. As it turned out, ever since that first glimce, I have spent

many wonderful hours in that chair under the ministrations of Jane, its owner and very

skilled operator.

At Jane’s suggestions, I removed my skirt and top, leaving me rather fully exposed to

my hostess and her party. Jane recognized my discomfort and suggested that I have a

seat at the vanity. In short order, I was seated at the delicate swivel chair. Considering

my definite lack of need for a makeover at present, Jane and Karen thought it best to

go right to Step 2 in my journey into feminization. I wasn't exactly sure what Step 2

was, but I didn't have to wait long. Given the choice, I opted to be blindfolded. After

securing said blindfold, someone swiveled me around so that I was facing out away

from the vanity table. It was time, they said, for me to get my first taste of a man's

penis. I was told not to worry—that they would start me off with a realistic dildo.

Tentatively at first, I opened my mouth. It's true that I'd sucked on realistic dildos during

my closet sessions in my house, this was a completely different story. Soon, I felt the

tip of a VERY realsitic penis eased into my awaiting mouth. Whomever was

manipulating it worked with me, never giving me more of the thing than I could handle.

It had become clear by now that this was no dildo--it must have been something that

Ricki had been hiding in her panties. She gently palced her hands on the top and back

of my head and skillfully guided me through my first (the first of many) blowjob. It was

an exquisite experience, notable for several details that I hadn't anticipated. The

texture of Ricki's penis was almost indescribably smooth. The smell that was a

combination of her perfume and precum made my head spin. The gentle bumping on

my neck of the hoop earrings resulting from the back-and-forth motion of my head

during the blowjob was a wonderful reminder of how much further down the road

toward feminization I'd come in just the time since I'd pulled into Karen's driveway. I

loved how Ricki's penis seemd to engorge an extra measure, further tightening the

skin on his penis, making it larger and smoother as he neared climax. And of course,

the taste of Ricki's juice, when it finally exploded into my mouth was wonderful. It all

was unforgettable.

That night was the start of a whole new life for me--one that I had long dreamed about.

COMMENTS AS USUAL WELCOME, GOOD OR BAD, ANY IDEAS FOR A

CONTINUATION?

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When facebook was not so famous, everyone busy with orkut, one day when I open my orkut there was an alert saying suman want to be friend with you. It was a new face to me but I went through her profile and I observed my wife and my brother already in her friend’s list. I thought she might be our far relative, whom I don’t know personally. I accepted her request, later in the evening I asked my wife, who is this suman, she said she also doesn’t know, and she accepted her request blindly. One...

2 years ago
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From friend to crush to friendzoned cuck part 5

We woke up from our nap a couple hours later. I got dressed and we acted like nothing crazy happened. We went to her living room and started hanging out there. We poured some drinks, sat around, watched tv and talked. It was honestly nice to have a normal conversation again, not to have anything sexual come up. But then it happened, I started having feelings for her again. I thought I was done, but as we sat there enjoying each other's company, I couldn't help it. I started thinking about how I...

2 years ago
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Renewing a Relationship

She had taken no more than a few steps in the direction of her car when she saw me leaning against the limo watching her interestedly. Meredith knew the reason being this close to me made her heart beat erratically and she urgently quickened her pace. Unknown to Meredith, I had silently walked up right behind her. Suddenly, I roughly grabbed her wrist and pulled her towards me. She immediately turned around to face me. " What is wrong with you?" she shot at me irritably as she...

1 year ago
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My Girlfriends Best friend

(Left out some descriptions so you can imagine whoever you want) I had occasionally fantasized about my girlfriend's friend Lucy, but I never thought she felt the same way. My girlfriend Rebecca, Lucy and I all go to the same high school. Being a great guitar player I usually brought my guitar to school and played during lunch times, on occasion we would get a sing along to our favorite bands such as pearl jam and red-hot chili-peppers. Lucy would always sit next to me during these...

4 years ago
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The United Kingdom of Zoo A fake BBC documentary seriess8e19 Sharon Callaghan 37 from Newcastle

We begin with a mini-montage of life in Newcastle-upon-Tyne ... A shot of Gray’s Monument, of the busy Eldon Square shopping center, St James’ Park football stadium, before we find ourselves in a busy street, looking up at an impressive, and very modern looking 5 story glass fronted building. We can see through the glass walls, seeing the staircases and offices inside. And then, stepping into frame from the side, trying not the block the architectural masterpiece – another masterpiece of...

1 year ago
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New Boyfriends Girlfriends

After Sue and I broke up, I was quite depressed. Sue is a fantastic woman. She is smart, funny, and beautiful. Also, she is great in bed. She has a model's body--34A-24-34--and she keeps herself in good shape. My cock gets hard just from thinking about her. When we first started going out, she was a little inexperienced. I was the first guy she did it with while the lights were on. I was the first guy to cum in her mouth. Despite this, she surprised me several times, like the time she took...

3 years ago
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Newer Level Of friendship

Newer Level Of FriendshipBy: Londebaaz Chohan Narayan was almost 5 10, dark black hair and he had hazel brown eyes. He never been to a gym but was an avid jogger man with a very nice physical appearance. Rishi on the other hand was about 5’ 8’’ a bit over weight about 190 pounds of meat but still looked in pretty good shape. They almost were never together doing any exercise but as they rented a two bedroom apartment together in the college town, it was only an accident that they saw each...

3 years ago
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Friend to crush to friendzoned cuck part 10

Some time had passed since I last hung out with Sarah. She seemed to want to go back to our old ways of friendship, so I think she was starting to avoid me. We would text here and there, but nothing too much. If she wanted to go back to a normal friendship, then I would accept that, although I would be a little sad about it.In the meantime, I was frequently joining in with Rachel and Eric. It was always so hot watching them. Sometimes it was so passionate, other times it was rough fucking. They...

3 years ago
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Old Friends New Lovers

Jennifer and Jason were best friends in high school. In all honesty, if they had not both been born and raised in a rural south Alabama town, they would have possibly been more. The racial tension in their town was not like some, but in the early nineties, a mixed couple was still frowned upon.Jennifer was a beautiful African-American young lady in high school. She had all the qualities that Jason liked in a woman. Not only was she beautiful, but she was smart, athletic and had a sense of...

Interracial
3 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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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...

3 years ago
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Response To My Story Leads To New Relationship

Would like to thank ISS for making this happened bcoz of your website I met with a memorable encounter with a south India dusky beauty. Well coming to the story which is true no fiction, last year I posted an story and got many one mail appreciation and among them was a mail which looked more impressed and sweet and I replied to the mail and I had waited for nearly 2-3 week for the response and then it all started. I thanked her for the mail and she replied back as well narrated and every mail...

3 years ago
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Centerfold

Jim McGuire skidded his bike to a stop in front of the large blue sided house. Setting the bike up against the white picket fence, the eighteen-year-old glanced at his watch. He smiled as he saw that he was right on time. Not that Mrs. Burke would've been angry if he had been a little late, but it was a matter of pride to the sandy-haired young man that he showed up places when he said he would. Originally, he had planned to spend this week in Florida. His parents had promised him a trip to...

1 year ago
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Harold

I finally made it, I have a full football scholarship to a small college and I’m away from home, for the first time in my life. I checked in, they had a whole staff to help you if you needed it, but I was fine, so I got my schedules, both football and academic and the key to my room. I knew I was getting a roommate, it was a small school and I was curious to see how the luck of the draw worked for me. He was already in the room and unpacked when I got there, it took me all of thirty seconds to...

Gay
3 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...

2 years ago
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Harold and Wendy

This is my first short story, any feedback would be welcomed. I’m planning on writing more so let me know how to improve. Hope you enjoy. ***** Harold Thompson has woken up promptly at 8 o’clock every morning for the last six months and sees nothing but an empty side of the bed where his wife used to sleep. Her name was Deanna. He thinks about her every day how she’d always smile as he woke up and tells him good morning. Now there are no more good mornings for Harold. At age 56, Harold was...

3 years ago
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Goldilocks the sexy version

It was a crisp winter’s day and Danielle was on her way to see a friend to try out her new double-ender. It was quite a walk, circumnavigating the big wood between their villages. Her Mum had always said to never go through the wood. There were tales of wolves and tigers, waiting in the deepest, darkest parts of the forest. Danielle thought this somewhat unlikely, being in West Yorkshire, but it still made her a bit weary. Danielle was known to all her friends as Goldilocks, on account of her...

3 years ago
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Goldilocks the sexy version

It was a crisp winter's day and Danielle was on her way to see a friend to try out her new double-ender. It was quite a walk, circumnavigating the big wood between their villages. Her Mum had always said to never go through the wood. There were tales of wolves and tigers, waiting in the deepest, darkest parts of the forest. Danielle thought this somewhat unlikely, being in West Yorkshire, but it still made her a bit weary. Danielle was known to all her friends as Goldilocks, on account of her...

Straight Sex
4 years ago
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GOLDILOCKS

STARTING YOUNGGoldilocks, yes she had hair like that, absolutely right, down to her navel. But who was she really?Photographing her, painting her. Reaching under her short little Catholic skirt and touching the silk of her naked thighs, I thought of all that, too, I have to admit. I thought of kissing her, seeing if her face was as soft as it looked - baby flesh.Yes, it was there from the start, especially once she gave me the age-old inviting smile and her eyes became, for a moment, a woman’s...

2 years ago
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Making new friends Strange Relationship

Originally I had no intention at all of meeting Ben again, it was the girls who talked me into it. Once I’d confessed to them that we’d met up for a drink, they were full of questions. None of them particularly like Richard, even though they haven’t met him. But they’ve all been around when I’ve had texts telling me he was going to be late, or heard him on the phone breaking a date. They never thought to ask how far Ben and I had gone on the date, which was good because I wouldn’t have been...

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,...

4 years ago
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Old Friend New Flame 8211 Love And Lust With A School Friend

This is a story about how i met my school friend lets call her M after a very long time. U can send me your comments and anybody interested in chatting can mail me at yahoo.in It was an usual day after work i was tired and i was pinged on my fb messenger by M. I had forgotten her existence as v went to school together and after that i forgot her existence only. Slowly v started chatting and became close she even used to send me her pics and stuff. Casually it became more intimate v wanted to...

3 years ago
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Harold Saves Her Husband Part 01

Harold saves her husband (Part 1)This is a sequel to the earlier story “Harold Plays The Hero” ************************************************* Copyright Oggbashan June 2006The author asserts the moral right to be identified as the author of this work.This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons.This is the first part of the sequel. . ...

3 years ago
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Harold Saves Her Husband Part 03 and Last

Harold Saves Her Husband Part Three Copyright Oggbashan July 2014The author asserts the moral right to be identified as the author of this work.This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons.Although apparently set in part of 19th Century India, the locations, incidents, customs and activities are in a fictional world that does not, and did not,...

1 year ago
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Cuckolding Positive For Some Couples

Cuckolding Can Be Positive For Some Couples, Study SaysBy Ian Kerner, CNNActing on adulterous fantasies may strengthen a relationship, as counterintuitive as it may sound.Cuckolding has become fetishized into a powerful sexual fantasy for some.Sometimes just sharing a sexy thought can be arousing enough -- you don't have to follow through...(CNN)In our current political climate, the term "cuck" -- short for "cuckservative" -- has become an insult of the so-called alt-right, aimed at men they...

2 years ago
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Harolds First Time Part I

There is one thing in this world that will always be consistent, the sexual desires of a teenage boy for older women who are clearly out of their league. Having been a teenage boy and knowing how much truth there is to it I decided a little story about a young G.I. and a barber might be something worth sharing…Harold was 17 years old when he enlisted into the military. He was about 6 foot tall, 160 to 175 lbs, medium build, black, and in pretty good shape due to high school athletics. He was...

3 years ago
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How To Introduce Sex Toys Into Your Relationship

How To Introduce Sex Toys Into Your Relationship Sex Toys are Fun. Most couples get bored with their sex lives at some point in their relationships. Sex toys add a bit of zest to the relationship and keep things from getting dull. Using a sex toy together can bring you closer; sharing new experiences together can be very intimate. I didn't try using a sex toy until I was 28. Although I've always been open-minded, fairly sexual and comfortable with my body, I'd never gotten around to actually...

2 years ago
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Cuckolding My Small Dick Boyfriend

Fucking my small dick boyfriend Jack was fun, but it was getting old and I was in need of some bigger cock. Now don’t get me wrong, my boyfriend is a great guy, but in the arena of hot sex, he was just not big enough to satisfy me. This is where my friend Terrance comes into the picture. It was a rainy and cold Saturday night and we were sitting around the house watching a movie not doing much of anything. I told him that I had a friend coming over to hang out with us, but I don’t think he...

1 year ago
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Arnolds Little Friend

Arnold Sebastian Stuart is a geeky nerd and has one little friend between his legs. He’s always been a big loser and has constantly been picked on. But now that he’s older than 18… things begin to escalate. So far Arnold has been able to keep his privates private… his one inch nub and all, but things are about to change… —— This story is humiliation focused. It’s not supposed to be wholesome. Although it can have wholesome moments. I’m experimenting with the idea of limited rules so as long as...

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