Night of Many Firsts Part 3
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I have been crossdressing in private since I was young. Now in my late forties and after three failed marriages, I had decided to step outside as Jessica.So after a lot of planning over several months, the day had finally come.I stepped in the bath as JD and shaved any hairs on my body that should not be there. It did not take long as I had been preparing my body for weeks to be smooth. I stepped out of the bath as Jessica and dried myself off. I wrapped the towel around myself just like any...
CrossdressingA Day of Firsts by Kathy Nelson [email protected] (c):Kathryn Nelson, 1998 It was one of those hectic work periods where I was putting in 70 to 80 hours a week. You know, when there's no time for anything else in your life except the job. But, thank god the rush was over and it looked like things were going to calm down. Friday night had come around and I was going home at a decent hour. I even had the whole weekend off and I was ready to celebrate. Well, more like...
The bar was crowded for the big football game. Standing room only. I was alone but hoped to find another regular to watch the game with. I ordered a beer and resigned myself to a disappointing spectacle. A good game was much more enhanced when watching with a familiar face or two. Halfway through my beer, I see Jim walk in. Jim was a guy a frequently chatted with and we really hit it off. He was the perfect guy to watch the game with. I flagged him over, shook hands and told him "Looks like...
SeductionMy 4th Bi experience happened that night of my 3rd experience. I'll never forget it was on a Saturday,Sept 24 1983. I was 16. It was 7:16 pm when I looked at the clock for what seemed like the millionth time. My parents were down the street at another neighbors house. I was sitting in my bedroom wondering what time I should go over to Charles house the anticipation was killing me. Earlier that day he asked if I wanted to come over tonight but what time should I go? I had occasionally looked out...
Eric watched with unblinking eyes as the tiny panties revealed a small but erect cock hidden underneath, and that was another first for him. The stunning woman before him had just pulled her panties down and revealed a cock and he was not repulsed. Tonya's head was bowed in shame with this act. To her, it was like showing off a birth defect. Eric responded by placing his fist under her chin and gently raised it up and looked her in the eyes. He gave her a warm smile and then removed his boxer...
TransI hope you enjoy it. Please PM me or comment below and let me know what you thought. Of course I also encourage voting. If you go into the Forum section of the site you will see the Sex Stories Section. The CAW10 entries are there... I strongly suggest reading them as they are wonderful and written by very talented people. Enjoy! A Confession – A Night of Firsts I am a bit worried as I write this. Mostly because of what I have done and what I know, with absolute certainty, I...
Introduction: A teen girl meets the guy she wants to make her a woman. Hello! Thank you to everyone who has been encouraging me to keep writing. This story is not intended to be part of a series, but I hope it is well received. I hope you enjoy it. Please PM me or comment below and let me know what you thought. Of course I also encourage voting. If you go into the Forum section of the site you will see the Sex Stories Section. The CAW10 entries are there… I strongly suggest reading them as...
Dedicated to a lovely young lady that would have graduated in 1960 with a first initial of "J" First and most important, this is a totally true story. Because it is true, there is little sex and what there is, has not been embellished to the best of my knowledge. One almost always remembers their "Firsts." Their first kiss, first date, first love, first sex and first crush. This is a story of all the above and more. I have always been a shy person. All through my freshman and sophomore...
Anita lay naked on the bed, her body trembling with anticipation. Her small breasts heaved against her chest as she looked at him. Her eyes focused on his finger tips as they reached into the waistband of his black boxer briefs. A fairly significant bulge stuck out. She knew it was going to hurt. But she didn't care. She wanted to feel a cock inside her for the very first time. It was Alicia who suggested Bobby.Bobby and Anita had known each other for about a year, they met through Alicia. She...
It’s funny how simple things trigger memories in a person. Sights, sounds, smells and even feelings of pain or pleasure can spark a flashback. That pain I was now feeling as my cock strained against denim made me recall how all this began. 15 Months Earlier It was Friday night, not long after leaving work, where I found myself in my favorite place. My home away from home, at least from the time just prior to my divorce until now, where I could relax before heading home or in this case to...
January 1981, Milford, Ohio On Monday morning at school, Tracey Jones pulled me aside and told me she had a question she needed to ask me. She and I were on different lunches, so I asked if I could call her, but she wanted to talk face-to-face. I suggested that I’d drop by her house after I saw Doctor Mercer that evening if she wanted, and she was fine with that. When I walked into Miss Barkhurst’s class, where I was the teaching assistant, I sighed. Dona Bingham was in this class. She...
I was never a big hit with the girls in High School and I was a virgin by the time I graduated. Now with living at home and just working I didn't have a real chance to date. It was the 80's and I didn't have a computer yet and when I hit at the age of 18 I was able to go to the Adult bookstores and I was a k** in the candy store. Well I would gather up some masturbating supplies and race home to jerk off, some of the items I would get were the local swingers magazine. I figured that I wanted to...
I was a horny but shy guy in school and I never had the guts to ask girls out. After getting out of high school I finally had to shed my virginity. I was a regular at the local adult bookstore and I decided to get a swingers magazine. I still lived at home so I had to try to find someone to host After sending several letters out I got a reply back from Joe and Patty, they were in their mid 40’s. Patty was a tiny blond with a nice body. Joe was a taller guy 6’3” about 250 with a slight beer gut....
I was a horny but shy guy in school and I never had the guts to ask girls out. After getting out of high school I finally had to shed my virginity. I was a regular at the local adult bookstore and I decided to get a swingers magazine. I still lived at home so I had to try to find someone to host After sending several letters out I got a reply back from Joe and Patty, they were in their mid 40’s. Patty was a tiny blond with a nice body. Joe was a taller guy 6’3” about 250 with a slight beer gut....
I was never a big hit with the girls in High School and I was a virgin by the time I graduated. Now with living at home and just working I didn't have a real chance to date. It was the 80's and I didn't have a computer yet and when I hit at the age of 18 I was able to go to the Adult bookstores and I was a k** in the candy store. Well I would gather up some masturbating supplies and race home to jerk off, some of the items I would get were the local swingers magazine. I figured that I wanted to...
Night of Many firsts (Part Two)Don Abdul ©He leads her to a particular spot and then seals his lips over hers, it feels as though they are both going to explode with lust after their lips touch. He draws her even closer into the whirlwind of their passionate kiss. Then she feels his hands reach into the neckline of her top, suspecting that he wants to feel her unclad bosom. To her surprise though what she experiences next is not the feel of his hands on her tits, but the ripping sound of her...
I opened the door to the club and walked inside. From the outside, the older brick building looked sort of run down, but once inside I found myself in a club with large bar on one side, polished brass railings, mirrors, subdued lighting, tasteful seats at the bar, hardwood floors, tables, a few booths further away and at the very end of the club a large stage with karaoke being sung. This was no seedy dive bar, thank goodness.The lights, the music (karaoke music is always so loud as if...
CrossdressingThis was the summer of firsts. I was having so much fun knowing how much control I had over my neighbor. With a flick of my tongue I could send a wave of pure pleasure making his body convulse and cum involuntarily. The power and control was intoxicating. In the few weeks to follow we fooled around practically every day after school. He was slowly but surely becoming more and more comfortable with the idea that I was his slutty little cum dumpster. With some great joy and lots of practice, he...
First TimeNight of Many firsts (Part Two)Don Abdul ©He leads her to a particular spot and then seals his lips over hers, it feels as though they are both going to explode with lust after their lips touch. He draws her even closer into the whirlwind of their passionate kiss. Then she feels his hands reach into the neckline of her top, suspecting that he wants to feel her unclad bosom. To her surprise though what she experiences next is not the feel of his hands on her tits, but the ripping sound of her...
BisexualA Night of Firsts By Sexy Laura This story is property of me, and may not be resubmitted without my consent. [email protected] ************************* "Tommy.. Can you give me a hand for a second?? Please???" I hated when my sister Shelley asked me for a favor when she had clients over. I always feel uncomfortable. Especially since my sister has a clientele that is slightly different then most people would imagine. She is a professional dominatrix. Complete with the...
Night of Many firsts (Part One)Don Abdul ©She was engaged to be married, but a couple of weeks to the wedding, her whole world came crashing down around her, when she received an anonymous tip that took her to a motel on the edge of town. At the motel, she caught her man, and her would-be maid of honor, stepping out from a raunchy fuck fest…..The trauma of that incident and the heartbreak it caused her would have put some other person in a sanatorium. Dawn however is a sister with attitude, so,...
Night of Many firsts (Part One)Don Abdul ©She was engaged to be married, but a couple of weeks to the wedding, her whole world came crashing down around her, when she received an anonymous tip that took her to a motel on the edge of town. At the motel, she caught her man, and her would-be maid of honor, stepping out from a raunchy fuck fest.....The trauma of that incident and the heartbreak it caused her would have put some other person in a sanatorium. Dawn however is a sister with attitude,...
BisexualChapter 1 I'll bet you remember your first time, right? For sex. Yeah. Well, I do. It was last Saturday. I had been dating my boyfriend, Rick, for about six months, he's seventeen, six months to the day older than I am. We had fooled around a bit, I'd jacked him off some, he'd gotten my top and bra off and had sucked my boobs. Oh, was that great. It's the first time my panties got real wet, oh, I loved it. Anyway, my parents were going out of town over the weekend and my best friend, Lindsey,...
First TimeChapter 1 I'll bet you remember your first time, right? For sex. Yeah. Well, I do. It was last Saturday. I had been dating my boyfriend, Rick, for about six months, he's sixteen, six months to the day older than I am. We had fooled around a bit, I'd jacked him off some, he'd gotten my top and bra off and had sucked my boobs. Oh, was that great. It's the first time my panties got real wet, oh, I loved it. Anyway, my parents were going out of town over the weekend and my best friend,...
I was 20 years old, a sophomore in college, and was living in an apartment with a friend off campus for the first time in my life. No one in my circle of friends had any idea that I had always felt like I was a girl in my mind. Living in the deep south in the 90’s, it wasn’t an option to be honest with people. If you had these feelings, it would be in your best interests to store them as far back in your mind as you possibly could. No one had a clue that I wore panties almost exclusively....
Chapter 1 I’ll bet you remember your first time, right? For sex. Yeah. Well, I do. It was last Saturday. I had been dating my boyfriend, Rick, for about six months, he’s seventeen, six months to the day older than I am. We had fooled around a bit, I’d jacked him off some, he’d gotten my top and bra off and had sucked my boobs. Oh, was that great. It’s the first time my panties got real wet, oh, I loved it. Anyway, my parents were going out of town over the weekend and my best friend,...
First day of school for both Murphy kids saw a return of a family tradition: Mom fixed a full breakfast for everyone. Pancakes, bacon, sausage, eggs, fruits and all kinds of baked goods. She generally cooks for the family, then the mothers from the neighborhood carpool come and enjoy a wonderful meal at their own pace. There were usually a few empty bottles of wine in the trash when the kids returned home from the first day of school. Rumor has it the same carpoolers also got together toward...
Reassured of my dominance, I licked his cum off my hands and went back to his friend. I patted his hard cock on my tongue, moaning playfully. I was having the time of my life, people were stopping in the street to watch, and I was loving it. I took the second man’s cock back into my mouth again and again, slowing going deeper each time. Then I kept my tongue out, flicking along the underside of his shaft as I took him down my throat. As the tip of my tongue touched his balls, he came, sending a...
First TimeThe date did not get off to a good start. I arrived early as always, ordered a drink and found a nice seat outside to enjoy the amazing summer sun that for once was beating down on London. As the minutes ticked by I began to think that I’d been stood up. Suddenly, fifteen minutes late, my phone buzzed with a message apologising but assuring me she was on her way.She finally arrived thirty minutes late and I was taken aback - she had looked very cute online but her picture really didn’t do her...
True"Mr. Clinton, this is Brian Frost." "Hello, Brian." Did he sound exceptionally cool? "Sir, I have been given the privilege of accompanying your daughter, Cassandra, on her first official date this Saturday." "I'm aware. She told me months ago. I suppose there isn't much I can say about it, now. What is it you wanted?" "I wanted to make sure my choice of activities would meet with your approval before I purchased the tickets. The Notre Dame Ballet Company is performing...
I invite all my fine female dear readers to respond to this sweet sexy survey of their first time erotic experiences.I take my inspiration from a very successfull short blog, in terms of the ever growing number of responses it gets.I try to be a bit more precise in my private intimate inquiry, stating several sets of questions related to this subject.I hotly hope we will get to read loads of cunning comments from warm women wanting to share some sexy secrets!I often wonder how much women differ...
OK this time in my life was turbulent, as far as sexual relations developed, with here I am at the beginning of the Sexual Revolution, Vietnam Protests, Protests in general, Peace Love Dope, Flower Power, Flower c***dren, Acid Rock, Jimi Hendrix, Janis Joplin, Timothy Leary, even the dawn of Gay Rights. That plus I had a head start in knowledge. I was torn between what I was taught was proper and paths others led me down. My girlfriend, which I was taught was the normal thing, I thought, where...
"I need to find someone to take me camping," she said while standing in my cubicle. We'd just been talking about how much we enjoyed camping and the outdoors and I'd been showing her some of my nature photos. I can't even remember what brought it all up, but it was fun to open up with a coworker like that. I like to feel the intimacy that comes from opening up to others and having them accept me. It's even better when we have similar interests and I can feel that rapport growing almost...
January 1981, Milford, Ohio I slowly slid my hand down Kara’s stomach until my fingers touched her soft pubic hair. I twirled my fingers lightly in that downy softness for a bit, then asked her to spread her legs. She moved them slightly apart, and I slid a single finger down to her labia and started gently rubbing in a circle. She gasped at the contact and her breathing sped up. I continued with very light pressure, probing between her lips for her clit. She jerked suddenly, gasping when I...
We had been building up to this for many months. She was the gorgeous account manager, I was the admiring customer. She had captivated me from the first moment we met, and countless texts, emails and phone calls later, I knew she was someone very special. Innocent on the outside, something much more intriguing on the inside. After a fabulous dinner, followed by a few drinks in one of those hidden bars that only the locals know in my town, she boldly told me it was high time I delivered one of...
We all took a sip of our drink. Catherine, Anna and myself, presided over by Lauren. I felt like a new gurl at this party. I bit my lower lip, I wriggled in my seat for my dress giving an accidental glimpse of way too much upper pantyhosed thigh.I blushed so deeply. Lauren must have sensed it as she leaned in closer and told me that I was a flirty gurl and those legs of mine might get me in trouble. I lowered my eyes and she giggled when I didn't meet her gaze. I fumbled for conversation until...
CrossdressingDavid Miller and his wife Mandy were an attractive looking couple in their late thirties. Mandy stood just under five and a half feet, with David nearly six. Though David had always admired his wife's full rounded breasts as being one of her major attributes, her tight muscular ass was certainly another which he couldn't help but reach out and fondle whenever she walked by. Mandy of course thought her eyes to be her best feature, an almost cobalt blue that was accentuated greatly by her near...
I stood outside Mark’s door starting to doubt myself when it opened, and there he stood with this look that clearly said he was impressed with me, and my fear eased.“Wow Red, you are as bold as I hoped you’d be,” Mark said and pulled me inside.Stumbling into the room, I watched as he closed and locked the door. “How did you get away from the watchful eye of my sister?”“She was with her boyfriend. She wasn’t paying any attention to me.”Mark flopped on his bed and motioned for me to climb on....
First TimeMy encounter at the Seattle ABS frightened me so much that is was three or four months before I would go into another one and I had transferred to San Diego in the meantime.I had been thinking about that blowjob and decided that since I had enjoyed it so much I was curious to try some more and what better place to try to find more than another ABS. There were a few of them some distance from the base so it seemed safe. This was back before Don’t Ask Don’t Tell so the services were still...
Robbie wanted to take his time over this; to make sure Zoe's first time was perfect. She however, had other ideas. Sleeping with Robbie had never been far from her mind over the past few weeks and she couldn't get him upstairs fast enough. She took his hand and tugged him along behind her, only pausing once she had led them both to her room. Turning, she began to tug at his shirt, eager to get it off. "Zoe, slow down, this is not how your first time should be. It's too rushed, we should...
January 1981, Milford, Ohio On Monday, when I sat down beside Kara in chemistry class, she reached over and squeezed my hand. “Kara, let’s have lunch, I need to tell you what happened on Saturday.” “OK. I’ll meet you at the computer lab.” I dropped my hand to her knee and squeezed as the bell rang and Kara smiled. At lunch, I stopped to tell Bethany I’d be talking to Kara and then went to the computer lab. Kara arrived just about the same time I did. I unlocked the door, and we went...
It looked like it would be an absolutely terrible Holiday Break for me. As an orphan, having been abandoned by my mother just days after birth and having never known my father, I had no family to go home to, for I had never been adopted. Even though there were some 3,000 students at my college, it had just happened that all my friends were either from the southern or western states, and I could not afford the airfare and spending money to go with them for the Holiday Break to spend the time...
Thursday December 13 had been the end of the first semester for me, for that was the night of my last final exam. One week later, the date would be forever memorable for me because it was the day my companion and I were rescued from our isolation. It was nearly sunset when the work crew had finally cleared away the snow from the north-side door. I sent Megumi out first, and someone quickly grabbed her suitcase while someone else wrapped a large thick blanket around her and hurried her to an...
We find Eric St Clare naked and under the sheets of king size hotel bed, oblivious to the rain and thunder outside. His arms are wrapped around a stunning dark haired beauty clad only in nylons and garter belt. They are sharing gentle kisses on each other's necks and lips as Eric allows his hands to run across her naked breasts as well as her nylon covered legs.A soft moan escapes the brunette's red parted lips as Eric slowly draws his fingertips up the back of her leg and he marvels at the...
TransSummer was definitely upon us. The heat had risen, but was not yet uncomfortable. I had traded in heavy coats and pants for tank tops, skirts and shorts. The end of my junior year of high school was quickly approaching. All and all the year had been slightly uneventful beyond the usual adjustment of getting used to the high school mentality. Since it wasn’t freezing cold outside I had begun to walk to and from school instead of catching the bus. It was on these walks I got to know my neighbor....
First TimeI should probably start off this story by saying that all of what I am about to put is in fact real and happened to me a few years ago when I had just turned 20 and is not exaggerated in anyway. In fact I'll have to keep some of what happened out of the story so I stick to the rules. I will try articulate it as best as I can. Hopefully I won't get too descriptive and make it too long.This night started like most nights when I lived at home, desperate to sneak away have sex and come back without...
Note about the formatting: text between sets of ":::" shows which character's perspective that portion is in.----Thursday Night---- :::George::: George collapsed on the bed next to his girlfriend Lucy. “That was the best yet sweet buns. Night”. He laid down his head, closed his eyes, and smiled as remembered the big game the next day. “George Hallis Lindern, what do I tell you day after day?” “Like I care?” He heard Lucy give an audible sigh. “Sometimes I don't know why I stay with you. You...
First TimeSome time ago my older sister caught me out in the Rumpus room with a girlie magazine. I was having a quiet wank over a full page layout of a gorgeous blonde bird who was sprawled out on a bed working on her fat juicy pussy with a huge dildo. I was only 14 at the time and my sister was a well developed 15 year old and aggressive with it. She grabbed my mag. and with a wicked grin she flounced off out of the room calling over her shoulder "I've got you now you little bastard, one peep out of...
Labor Day was the busiest day of the season for Dad and his Parks and Recreation staff. The parks would be full and it was the last day they had the public pools open. Greg and I always had to help in some way. For some reason Greg had gotten out of helping this time. He got up early and left for the day. Dad made me help the lifeguards at the main pool. You had to be 16 to do it for money so I was an unpaid volunteer, or that was what Dad told me. By 11:00 am the pool was packed. It was a...
Friday night is friends night out night, Six of us have always tried our best over the years after school to save at least one night a month to stay in touch so the last Friday of each month was saved for those that we're available to get together. This has been a ritual for the last several years. One member of the group was new and a close friend of one of the old group. Her name was Peggy, she didn't attend school with us but was invited into our close group. She was very quiet but smiled...
I was out of town on a business trip. Work ran late at the client's office and I was a little tired, but really wanted a drink. Not knowing the area, I just drove around until I found a decent-looking bar. As I made my way in, I only noticed that the lights were dim and the bar was set up like a relaxed club. The theme was very post-modern and there was electronic music playing in the background, but nothing too loud. I streamlined my way to the bar and asked for a drink. As soon...
The General sat behind his desk, grumbling to Chaz, who was ensconced in one of Michael's Shanghai Art Deco guest chairs. Chaz carefully hid his growing amusement. Bâtisse himself was now quartered in a pen out in the main dome near the base fire hall, with a replicator that pumped out carefully measured quantities of weed and shrubbery clippings every few hours. He was a source of endless fascination for everyone on base, young and old, and did not lack for visitors. "Only fucking goat...
My name is Josh I am 21 and I live with my girlfriend Ashley and her best friend Pamela. Ashley and I have been dating for 5 years. She is the most beautiful girl ever. She is 34-24-32, 5’5” and her hair was straight and black. Pamela was 5’3” had black hair measured 36-26-36. Ashley and I were very sexually active and she was very much bisexual so it was no surprise that the 3 of us had had a lot of threesomes and group sex. Ashley was very comfortable with me being sexually active with her...
Group SexIn 1989 my National Guard unit was activated to support Operation Just Cause, the invasion of Panama. Since we were a helicopter maintenance company, we knew that we would be busy but not have to see any action. Due to all the shots and paperwork that was needed, we got to Howard Air Force Base on the west coast of Panama after the fighting was over. My unit then set about helping the local maintenance staff repair all the birds that had been used hard during the invasion. We were there a few...
Gay MaleI have always had a desire for dressing femme and having submissive thoughts ever since I can remember. I started like many other gurls by trying on my mother's lingerie and loving it. Things gradually escalated to shaving (thankfully I am blonde and not very hairy naturally), experimenting with make-up, and inevitably sucking cock at the park toward the end of my college days. I was on my way to being a true sissy gurl now that I reflect on it. Everything I did was subconsciously geared toward...
I enjoyed giving my very first blow job and swallowing my first cum shot. I was hungry for more sexual experiences. I began to relive all the stories I’d overheard my sister telling her friends and every bit of porn I’d ever seen. I played with myself thinking about all of it. I was looking forward to trying them all out. Over the next few days after the blow job incident, every time we were out of earshot of other people, he would make subtle remarks and hints about how much fun he had. I let...
First Time"Ken?" my wife, Danielle, said to me one night while we were lying in bed. "Yea?" Here it comes, one of those "what are you thinking about" questions. Not quite. "When was your first time?" she asked. "Huh?" I said suprised. "You know, sex,"she said. "Mine?, you wouldn't want to here about it,"I said. "No, c'mon, I do." She snuggled up close to me. I put my hand up and ran my hand through her soft dark blonde hair. "Hmmmm, well,... My first time was back in ninth grade. "No...
January 1981, Milford, Ohio In chemistry class, Kara reminded me about our date. “As if I would forget!” I challenged. “I’ll pick you up at 5:00pm as promised! How about Chinese food tonight?” “That sounds good,” she said. “I have quite a few things to talk to you about, too!” “Did my dad give you the third degree?” “Kind of, but it’s more than that,” I said. The bell rang, preventing any further conversation. At lunch, I talked to Bethany. “I asked Elyse to go to the Sweetheart Dance...