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Old Man’s Folly

Author: Ben Barker
View as a PDF

Krissy’s Note: I totally fell in love with this story when I read it. The thought of meeting an older, romantic, businessman while having a drink is such a total turn-on. I love the romance that these two enjoy as well and this story really got my imagination firing away. Much thanks to the Author for allowing me to reproduce this story here on Transsexual Erotica Blog, and I hope you enjoy reading this beautiful story.

I was in the City to speak at a class on Business. I am in my 70′s but still very active and love to travel. I lost my wife of 51 years two years ago after a long and wonderful marriage. We had a very active life, extremely active in the sexual area. So with nothing else to do I make appearances at meetings etc rattling on about my success in business.

I checked into my room at the hotel, settled in and went to dinner alone. I chatted with some folks at the next table and was not tired when dinner was over so decided on a night cap in the lounge. It was packed but a 20 dollar bill in the hand of the right person found me a small booth for two. I ordered single malt on the rocks and began my usual pastime, watching people. There was a couple dancing that were very entertaining, her tits were bouncing all over the place.

And then I saw her. She was standing a few feet away looking around like trying to find a friend or something. I was absolutely stunned at her beauty. Very close to 6 feet tall, very slender with beautiful black hair that reached her waist. Small to medium breasts but the most stunning was her face. I was instantly in love. I said, “Miss,”

She looked down at me and smiled and I about fell to pieces.

“If you have no one to meet I would be really pleased if you would join me,” I said, nervous as a school boy.

She smiled, said thank you and slid in beside me. “I love this Hotel but this lounge is always so crowded.”

I offered my hand and said, “I’m Tony.”

She took my hand and replied, “I’m Lizabeth but please don’t call me Lizz or Lizzy,” with a smile.

I smiled back and said, “Agreed.”

I was no longer looking around at the crowd. I was intently studying the face of this beautiful person setting next to me. Looking, starring might better describe my action. She glanced at me a couple of times and when our eyes met I felt she was a little uncomfortable.

“I’m so sorry I am making you uncomfortable but you are sooo beautiful I just can’t help it.”

“Thank you for the compliment,” she replied.

We chatted about why I was here in the City and she said she was here for a meeting and was surprised to find out I was speaking there and we discussed why we got there on Friday when the meeting wasn’t until Monday. We got along really well so I decided to ask,

“It’s only 9:30, is there somewhere else you like in the City?”

“I love the Downtown Lounge she said but we will never get in this late.”

Our waiter was just walking by so I gave him a Fifty and said,

“Let’s go find out.”

She gave me a big smile and I melted a little more. We hailed a cab and headed for the DL as it was called. It was a 20 minute ride which gave us more time to get to know each other. I really liked this girl. She was smart, easy to talk to and very observant. I am sure she noticed a small bulge in my pants that was constant. When we got to the DL there was a line of about 30 people or so waiting. I took her hand and pulled her to the front of the line. I let the doorman see the Hundred, he nodded and took it and said follow me. We were led thru the main area, which was packed with people, up a few steps to a private lounge and over looked the dance floor. The lighting was very dim but we could see that all the tables and booths were full except one clear in the back. We were seated, ordered our drinks and settled in. The place was loud, hot and crowded and as our eyes adjusted to the dark we began to see that watching the dancers wasn’t the only thing going on. One guy was getting a lap dance and the way his dates skirt was up it was fairly evident she was riding the pole. Another was getting a hand job and at one table the gal was on her knees.

“This is quite a place,” I exclaimed.

“Yes it is, that’s why I like it here,” she replied.

“You must wish you were with a younger guy,” I offered.

“If I didn’t want to be here with you I wouldn’t have suggested it,” she said.

Of course I was completely blown away. This beautiful creature actually wanted to be here with me, a guy old enough to be her Father or maybe even her Grandfather. She took my arm in her hands and sort of rub her breast on it. My cock was sooo hard. Pretty soon one of her hands was rested on my thigh and she began patting. I decided what the hell so I took her face in my hands and kissed her beautiful lips. It was her tongue that started the dance and things took off from there. I carraced her breasts, wanting to kiss and suck her nipples. She unbuttoned a few so access was allowed. Then she unhooked the front of her bra so entrance was even easier. Her breasts were so firm and nipples so hard I bent down and kissed each one and suckled like a baby. Her hand was on my cock, rubbing it up and down. I so wanted to let it out but thought probably shouldn’t. I did however decide to go for her love zone.

I placed my hand on her leg right at the edge of her skirt and started slowly moving it towards her cunny. When I was about half way to my goal she placed her hand on mine and stopped the movement. I was a bit puzzled but didn’t say anything. She kissed me ear and whispered,

“You’re going to find something different down there.”

“What do you mean?” I asked.

“You are going to find what I have my hand on.”

It took a couple minutes of very awkward silence for it to sink in what she was trying to tell me.

“A cock?” I asked.

“Yes!”

I couldn’t believe it. The most beautiful woman I had ever seen, face, breasts, body, legs, complete with a cock. She relaxed her hand but didn’t move it then whispered, “My thong keeps it from showing but it’s there alright.”

She felt a little tense and nothing was said for a couple more minutes. I just sat there looking at the beautiful face really not believing that this was happening.

“Are you going to hit me?” she asked.

I kissed her, pushing my tongue into her mouth to show her my feelings hadn’t changed.

“Oh no little girl, I’m not going to hit you. I feel like I’ve died and gone to heaven.”

I finished my scotch and asked her if she’d like another glass of wine.

“No, we could call and have a bottle delivered to my room if you are interested.”

I was up and ready to leave in a second. She led the way out and we hailed a cab. As soon as we settled in she borrowed my phone and called the Hotel. I was very pleasantly surprised when she opened my pants and released my very hard cock. She stroked it while we kissed and then lowered her mouth and took it all the way down her throat. Because of my age I rarely have a climax but in no time I felt one coming. I advised her she best stop till we were in her room.

The wine was in her room all ready open with the cork back in the bottle. As I poured a couple glasses Lizabeth excused herself and went to the other room. I was sure she would reappear in something a little sexier but she didn’t. I offered her a glass of wine which she accepted and then turned a little music on, something soft but with a nice rhythm. Then she started moving her hips and doing a little dance for me. Her beautiful smile had me captivated. I barely noticed her undoing her blouse and tossing it aside. She caressed her breasts as her dance continued. Then her bra was off and her beautiful breasts were there for me to enjoy. One hand moved from breast to breast while the other hand moved down to her love zone. Her skirt was the next to go leaving her in just a white thong. She turned her back to me as she danced, bent over and spread her ass cheeks with her hands and then started pulling her thong down and off. Then this beautiful girl just swayed back and forth, enjoying being the center of attention. As her legs spread slightly I could see her ball sack. But I was completely blown away as she slowly turned around to face me.

This absolutely beautiful girl had the most amazing cock. It was all of 9 cut inches, very slender with a cycle helmet head, slightly smaller than the shaft. As she danced she moved towards me then bent over to rub her breasts on my face. As I nibble her nipples my hand grasped her cock and I took over the game. She stood up and I moved my mouth to her cock. It was very hard, very hot, yet very soft as it moved between my lips. I was in a daze on what to do. I wanted the feeling of her tongue in my mouth, I wanted to feel and kiss and nibble her tits and I wanted to suck her cock until she filled my mouth with love juice. So I did all three. As I kissed her and tended to her breasts I slowly stroked the hard meat in my hand. She was working my cock as we played. I had her cock deep in my throat when she held my head and told me to slow down or she was going to cum. I came up for air and she changed positions with me.

After stroking and sucking my very hard old cock this beautiful lady reached to the night stand and retrieved a tube of cream and squirted a little on my rosebud. Then she started fingering as she sucked by dick. I was just laying there enjoying as she fucked me with one finger then two and then three. There was a short break and then I felt the head of her hard meat pressed against my hole. She started with just the head then slowly moved her cock in and out until she was fucking me with almost all of her meat. It was the first time in my life that I had been fucked but I found out that I loved it. As she pushed her meat in and out of me she was also playing with my meat. I told her I was about to cum so she pulled her cock out and buried mine down her throat. I unloaded a tremendous amount of cum and she swallowed almost all of it. The last bit she let drizzle into my mouth just before she kissed me.

I was completely wasted, not really capable of continuing out game. Lizabeth realized this so slowly stroked her cock until she shot her load in my mouth. Then she snuggled up to me, kissed me and we both dropped off to sleep.

When I awoke I found my lover in exactly the same position she was when we dropped off. I just laid there looking at her beautiful, peaceful face. I realized how much I truly loved her even though I had known her for less than 24 hours. She had a smile as if she knew I was gazing at her. I had to pee really bad so gently lowered her arm and head to the bed and slid out. I looked at the clock and it was 11:30. The last I remembered it was about 4 in the morning and that was just before we both shot our loads.

Lizabeth was still asleep when I returned so I decided to take a shower. I had just finished brushing my teeth when hands were soaping my back. I turned to find my lover smiling broadly as she soaped up and down my body and grasped my soft wiener with her hand. I kissed her briefly and told her I didn’t think I was up to playing. She continued to soap me until I took the soap and returned the favor. We rinsed off and exited the shower grabbing towels on our way out. I dried her and she dried me and laughed and kissed as we did.

“I’ve order breakfast for us,” she offered. “Hope you like hot cakes, eggs, bacon and coffee.”

“Sounds good to me,” I replied.

I went into the bathroom while the waiter delivered our food. Don’t know why because I’m sure he knew she wasn’t going to eat all of it. As we ate we chatted about what we wanted to do the rest of the day and she said,

“Sleep, play, sleep, play, in that order.”

“Well that gets us to about 4 o’clock tomorrow afternoon,” I replied with a laugh.

She stopped talking and just looked at me with this really sort of funny look on her face. She took a drink of coffee, got up and came over and sat on my lap.

“You know,” she started, “For some reason when I was standing there looking for a place to set in the Hotel lounge last night and you asked me to join you and I looked at you I knew right off we were going to get along really well together.”

“Well, I knew one thing for sure. The minute my eyes saw you I was in love.”

The Author of Old Man’s Folly
welcomes your questions and comments:
itsbeenfun99 at yahoo dot com

AUTHOR’S NOTE:
I hope you enjoyed my story. I know I probably should have called Lizabeth
a guy instead of a gal but to me she was just a beautiful woman that just
happened to have a cock.

Caramel And Devin

Author: Caramel
View as a PDF

Krissy’s Note: Caramel sent me this story after I did an interview with her for her excellent blog, Caramel’s Tgirls. Not sure if this is autobiographical or not but the rich imagery makes you feel like you were right there with the subject in this story. Pretty hot and I’m looking forward to reading more from Caramel in the future!

I began crossdressing at 12, but it wasn’t until I was 17 when I dressed up completely for the first time. When my parents went away for the weekend to Atlantic City, I took advantage of the opportunity to explore my feminine side to the fullest. As soon as they left the house that summer morning, I got out of bed, padded naked into the bathroom, drew myself a bath and poured a packet of Caswell & Massey sandalwood powder into the steaming water. The scent was like a forest after a heavy rain, the tiny suds crackling softly as I climbed into the tub and let the water’s heat seep into my body. After relaxing for awhile, I gave myself a panty shave, removing every trace of hair from my cock and balls. What remained was a thatch of slightly kinky tendrils just above the base of my shaft. I thought it looked pretty sexy. With that done, I stood up and turned on the shower and let the water drain out. The hot stream of needles pounding against my skin made me crazy with lust, but I resisted the urge to masturbate just yet.

I rinsed the last of the suds from my feet and stepped out of the bath, reaching for a large, thirsty white towel to dry my body. Next, I dusted my skin with a richly scented powder and a fine sable brush, then sat down at
the vanity to do my nails. Using an emery board, I buffed my toenails to artistic perfection and placed cotton balls between the spaces of each toe. I painted the nails scarlet red, carefully smoothing out the lustrous Chanel
varnish with the soft little bristles. I did my fingernails with French tips while my toes dried, thinking about how to do my hair and face. When my finger nails dried, I applied a generous amount of styling moose to my wet
curly hair and arranged a short, yet feminine couiffure. At 17, it didn’t take much makeup to make me look girlish. With just a little foundation, mascara, blush and a touch of red lipstick, I was ready to move on to the next step.

I entered my parent’s bedroom and went to my mom’s huge walk-in closet, surveying her highly sophisticated wardrobe. From the lingerie drawer, I picked out a pair of Lise Charmel panties and stepped into them. Then I
shimmied into a microscopic black YSL minidress with pointe d’esprit inserts at the sides. This dress was clearly meant to be worn with no undergarments, so I took the panties off, feeling my cock beginning to stir. The collection of sexy shoes included stiletto sandals, platforms with chunky heels, pumps with knotted vamps but I took a particular interest in a pair of black Charles Jourdan four inch sandals with three tiny straps to cross over the toes and lace bows at the centers. I was fascinated by how dainty my feet looked in the strappy lattice work of the skyscraper sandals, the cleavage of my red-painted toes criss-crossed by the gleaming straps of supple black leather. Within about ten minutes, I found myself walking in the sey heels with a sexy, hip-swaying stride. Just walking around the room was like an erotic exercise. The more I clicked across the floor, the more my swollen cock against the exquisitely form-fitting dress. Soon, I was literally trembling with lust. I went before the bedroom’s full-length mirror and posed in a variety of sexy stances, pausing for several moments when I looked my feminine best. While gazing at the points of my stiff nipples straining against the glimmering minidress, I imagined what it would look like if I had a firm set of breasts and by this time, clear streams of pre-cum were literally pouring from the swollen head of my erection.

I hoisted the hem of the dress up to my waist, curled my fingers around my shaft and began stroking it hard and fast. After about five minutes, my entire being exploded like a white-hot burst of energy. My body convulsed in a series of powerful spasms as my cock spurted rapid bursts of cum, splattering in a lewd rain across the mirror. I was so overtaken by the sheer force of my climax that I was barely aware of my own voice when I sharply cried out my self-loving passion. I’d experienced many great orgasms before, but this was definitely the most powerful ever. I loved dressing up completely and knew from then on that there would be no turning back.

One good thing about my having been a teenager before the Internet age began booming was that I had no knowledge about society’s labels. I didn’t understand the difference between crossdressing from transvestism or a
transgendered person from a transsexual. There was no pressure to try and figure out whether my secret past time was a sexual thing or something deeper. No one was going to find out about it anyway, right? I had the whole weekend all to myself to just be a girl. I only masturbated one more time that evening and only twice the next day which was highly unusual for a teenage hormone on two legs like me. I ended up just doing the same ordinary things I normally did on weekends; only dressed as a girl. Well, that’s not entirely true. I did put a bit of a spin on things, like cooking breakfast with nothing on but an apron and six inch wedge heels. I normally cut the lawn on Sundays in a t-shirt, jeans and sneakers, but this time I risked being watched by the neighbors doing this chore in a skimpy self-made pair of denim short-shorts, a high-cut pair of red satin panties, flip-flops and nothing to cover me up top. I’ll never know if anyone saw me dressed like this.

By the time the yard was finished and I’d taken a shower that day, I realized it was getting close to sundown and I knew that my parents would be back home in the next few hours. Sometimes they even returned an hour early
so I chose to be careful and put back everything the way I found it and get my homework done. I hated that Sunday evening realization that the weekend has flown by and it was responsibility time again. Within the next twelve hours, I’d be sitting in homeroom class all over again in boy mode with a bunch of people I hardly knew, except for one other kid.

My best friend, Devin Witherspoon was not only my best friend during my senior year of high school, but my only friend. He was a fellow honor student who sat next to me in homeroom class. Just like me, he was shy and
awkward; a wallflower at dances and extra-curricular activities. He could have dated just about any girl he wanted to if he knew what he had to offer. However, if he’d been aware of his good looks, he may have been impossible to deal with. His modesty seemed to enhance his sweet personality.

Upon learning that we lived near each other in our small northern New Jersey suburb at the beginning of the school year, we began walking to and from school together, eventually developing an easy, comfortable comradeship. We talked about everything, but my physical attraction to him was something I chose to keep to myself since I hadn’t yet come to terms with the fact that I might be bisexual. I’d always considered myself to be purely heterosexual, so my attraction really surprised and alarmed me.

I was quite certain that Devin was one the prettiest boy I’d ever met in my life. He had a thin, angular body and a certain feminine air about him combined with a look of rare serenity for someone so young. His demeanor was
one of quiet reserve, except for when he spoke about a subject that fascinated him. Then, his features would become animated with a lively intelligence which I found terribly appealing. I sometimes wondered if he’d ever experimented with makeup or feminine clothing, but of course, I couldn’t just come right out and ask him that. Instead, I just made use of every opportunity I had to just look at him without appearing in awe of him or love-struck.

His androgynous looks amazed me; pretty eyes as blue as a cloudless sky, fine aquiline nose and a wide, sensuous mouth , the edges of which were always upturned in just a trace of a smile. With his longish blonde hair curling crisply over his temples and high cheekbones, he reminded me of some of the flattest waif models that were so popular in the early 70s whose images graced the pages I’d seen in my mom’s issues of Vogue and Harper’s Bazaar. I’ve never any racial preference but thought our contrast would be pretty sexy, skin-to-skin.

The first time we made small talk in homeroom, I was acutely aware of the way his sexy, narrow eyes lingered over my face and body, not just once but two and three times. Could he be attracted to me, too? I wondered. I was so glad that we’d both chosen to sit at the very back desks of the room, where no one would notice how I allowed my eyes to drink in the sight of him when I thought he wouldn’t notice.

Devin introduced himself to me formally in the middle of our first conversation.

“By the way, I’m Devin”, he said in a quietly unassuming tone, extending his hand. I took his hand in mine and shook it from across from across our desks, letting mine linger just a moment longer than necessary when I told
him my name. His eyes dropped downward and a rosy hue came to his face. I realized that my flirty little handshake actually made him blush! Hopefully it wasn’t just wishful thinking on my part.

One day, while walking home from school, we tossed around the idea of catching a movie or going to the mall to hang out and people watch so we exchanged phone numbers. So there I was at home one night itching to call
him. I picked up the phone, dialed his number, but then stopped and hung up. I repeated this process three times before I finally allowed my call to go through. When he picked up, I didn’t really know what to say and asked him if I’d caught him at a bad time, half-hoping he’d tell me that I did.

“No, I was just doing some homework”, he replied.

“On a Saturday night” Devin? “Instead of hanging out with some hot girls?”

“Well, yeah. See, I had three dates lined up consecutively for tonight, but they all fell through.”

“That’s not funny. You could actually do that if you wanted too, if you put yourself out there.”

“Yeah, you too, kiddo. So what’s your excuse for being at home tonight?”

“My dates fell through, too.”

“Well, in that case, we might as well be doing our homework together.”

I couldn’t believe my ears when he asked so I invited him over.

“Yeah, but it’s like ten o’clock already. Wouldn’t your folks mind?”

“I’ve lost track of the time. Weren’t your parents going to Atlantic City again this weekend?”

“Yeah, Dev. They should be getting there just about now. They won’t mind the hour. I think they’ll be just glad to see I have a new friend.”

“Okay then,” he replied. “I’ll be there in about half an hour.”

We started out with art history in my room, which was one of my favorite subjects. Devin liked art, too, but couldn’t understand Picasso’s cubism so I tried my best to explain it to him.

“You’re pretty deep aren’t you?” he asked, once he started to get it.

“No, actually I’m pretty shallow, Dev.”

“You’re basically a loner like me, right?”

“Yep.”

“I thought at first that you had some sort of racial hang-up going on.”

“Why would you think something like that, Devin?”

“Well, there’s only a handful of other black kids at our school and you seemed to have some sort of special common friendliness with them. But then I’d see you talking with all different kinds of kids once in awhile and
decided that wasn’t it.”

“Yeah, I like everyone, Devin, even white kids like you.”

“So what did you think of me at first?”

“Do you really want me to answer that?”

“Sure, I’ve probably heard it before.”

“Okay. When I first saw you in homeroom class, I um, thought you were a girl at my first glance. I’m sorry. Maybe i shouldn’t have told you that.”

“Don’t be sorry. That’s nothing new. But why didn’t you change your seat or something once you realized that I wasn’t one? You didn’t mind being seen sitting next to such a girly boy?”

“I didn’t say it bothered me, did I?”

“Uh, no. I guess you didn’t.”

I couldn’t help but wonder if Devin was asking me what else I’d thought about him because I wondered if he was as attracted to me as I was to him. Thinking this would probably be the best time to find out for sure since we
had complete privacy for a change, I decided to go for it. I rose from the desk and began to leave the room.

“Hey, where are you going?” he asked.

“Keep studying,” I replied. I’ll be back in a few. And to answer your question, I think that you have an open mind, Dev. At least, I hope so.”

My opportunity to reveal my feminine side to Devin had finally arrived so I took total advantage of it, not knowing when it would come again. As soon as I reached my bedroom, I stripped out of my t-shirt and blue jeans. I’d already laid out a sexy outfit, having hoped things would turn out as well as they had so far. I sat at the edge of the bed, curled up one leg of my sheerest pair of black stockings and smoothed the soft fabric over my painted toes, up my calf and thigh , repeating the process with the other silky stocking. Then I stood up to pull the hose up my thighs, over my stiffening cock and around my hips. I wriggled my body into my favorite short, low-cut black lycra minidress which showed off the large points of my nipples and showcased my long smooth legs. In the bathroom, I put on a little makeup and lipstick and smoothed some finger waves into my hair with a little styling mousse. I was completely satisfied with my feminine look in my reflection in the mirror and it was now or never.

I slowly entered the study with my hips swaying ever so gently, awaiting Devin’s reaction.

“Oh my God, I almost didn’t recognize you , “he exclaimed. “Damn, you look hot.”

I let out a long sigh of relief. He asked me to turn around and I pirouetted with as much grace as I could muster.

“I always knew you’d look beautiful this way, but I didn’t expect you to…”

“…You’ve thought about seeing me dressed like this?”

“Yeah, but, wow. Even your voice sounds different now. How do you do that?”

“This is my natural voice really. I’d speak this way all the time if I didn’t have to act so boyish at school.”

Devin rose from behind the desk and came within a few feet from me.

“I know I’m gawking at you, but I just can’t get over the way you look. Do you know there’s not a soul in the world who wouldn’t think you weren’t a real girl looking like this?”

I’d been dressing like this for a few years, but I never thought I could actually fool anyone. I was convinced that Devin really thought that I looked like a real girl and a pretty one at that. Yet, I was still so nervous that my legs were shaking.

“I have a confession to make, “he offered shyly. “I dress up and try my best to look like a real girl, too, but I could never look as good as you do.”

“What are you talking about? You look like a girl even when you’re trying to look like a guy.”

“Well, I’ve never tried to completely transform myself. I have brothers and sisters at home, so there’s not much privacy.”

“Would you like to try it now, Devin?”

“You’ll help me?”

“Of course I’ll help you, silly. Come with me,” I said, making my way to the bathroom off my bedroom. I turned on the bath and told Devin to take off his clothes.

“Oh my God. You’re going to see me naked.”

“Don’t worry about it, hon. If it’ll make you feel more comfortable, I’ll get naked, too. We’ve both seen other guys naked in the locker rooms, right?”

“Yeah, but not each other.”

“Are you beginning to have second thoughts?”

“Yes, I am. So we’d better get on with this before I change my mind.”

I bubbled the bath water and only glanced at Devin now and then as not to make him more nervous than he already was. I saw that there was no hair on his flat, hard chest and his precisely rounded nipples and areole were the prettiest shades of pink. His tiny waist tapered down to an enticingly wide set of hips. Although his penis was flaccid, it was longer and thicker than I’d imagined it would be, with a heavily-veined shaft and a bulbous, smooth-fleshed crown. His legs were well-toned and long, ending in a trim set of narrow, dainty feet with the most adorable long pretty toes. I was dying to see Devin’s sizeable cock completely hard and I could feel his eyes on me as I peeled myself out of my dress, slipped out of my heels and paused for a few moments for effect before pulling my pantyhose down to expose my erect cock, which danced up and down lewdly once freed from its silky constraints.

When I was completely nude, Devin was too shy to really look at me directly. However, his cock was as hard as a roll of quarters, standing out from his loins and up toward his belly button as he stepped into the bathtub. Neither of us commented on one another’s naked bodies and Devin just smiled innocently as he sank into the steaming water.

I bathed him first with a soft cloth, then a loofah from the side of the tub. The tension was thick enough to cut with a knife and I broke it by jumping inside the tub with him and playfully splashing him with the bubbly water. He splashed back at me and we broke into a water fight, the two of us giggling and thrashing about like a wildly competitive pair of schoolgirls. The bathroom floor was soaked with water by the time we calmed down.

We got out of the tub and threw a few large, fluffy white towels on the floor, then entered my bedroom, our naked cocks bobbing this way and that respectively. Devin couldn’t seem to pry his eyes away from mine at first, then looked lower down my body.

“You must be proud to have such a big one, he said.”

“I don’t really think about it, “I responded. I really haven’t had much use for it yet.”

“You will soon I think.”

As soon as I tried to search for Devin’s eyes, he looked away, his shyness driving me crazy with desire.

“Oh, really? Ya think so?” I asked, moving toward him until we were close enough to be kissing. Devin froze and stared into my eyes. As badly as I wanted to touch him, I wouldn’t risk scaring him off and held myself back.

“Have a seat on the bed while I get you something to put on, ” I said, struggling to regain my composure.

Inside my closet, I found a pair of one of my most feminine, strappy high-heeled sandals from Via Spiga for Devin to try on. When he slid his feet into them, I fastened the delicate straps around his tiny ankles and had him stand up in them. The height of the heels strained his calves tautly, stretching his long firm thighs and elongating the symmetrical orbs of his plump, protuberant ass. Looking downward, he said, “I love the way they make me look, but I don’t know if Ill be able to walk in them.”

“It’ll take some practice, ” I admitted. “No one’s born knowing how to walk in high heels.”

I put on an equally tall pair of heels to guide him around the house until he learned how to move about with a sexy little sway. Then we spent the next hour or so changing in and out of various sexy outfits, doing each others hair and makeup and posing before the mirror together. At one point, I just couldn’t seem to stop staring at Devin and began to think of him as her.

She, Devin, was wearing an ensemble of mine of black lace, including a waist cinch that laced up the back with four ribbons to hold up the stockings and matching thong which barely encased her cock and balls. The underwire bra created the illusion of a sexy, feminine cleavage and her pretty pink nipples peeked through the lace. Her narrow, pedicured feet were arched upward in black patent leather mules with tapering five inch heels. All I had on was a lacy white LaPerla bra and panty set to show off my brown skin and a pair of five inch tall clear lucite platforms from Frederick’s of Hollywood. Devin had seen me in a variety of sexy outfits from my collection by now, but this one seemed to intrigue her more than anything else I’d worn. She became unusually quiet and somber and instead of looking at our reflections in the mirror, we found ourselves silently staring each other up and down. The next thing I knew, I found myself staring into her cool blue eyes that sparkled as if made out of crystal. I was in a daze when she leaned forward and planted a gentle kiss on my lips and then pulled back with her eyes full of question. She stepped away and brushed back a lock of hair that had slipped across her sweet, tender face.” I shouldn’t have done that”, she whispered. “I’m sorry.”

I reached out to her and pulled her against me gently. Her body was intensely hot and her heart was beating rapidly as I held her close. I moved a finger to trace the outline of her strawberry lips and she opened her mouth slightly with her eyes shut to allow my finger to slip inside and feel the wet heat of it. I leaned forward to kiss her soft cheek and said, “Don’t be sorry. I’m not. ”

I then pressed my lips to hers and the passion of our kiss rose to sensuous heights that left us both gasping for breath. I opened the front clasp of my brassiere and slid out of it. Devin’s eyes, which so often found it easier to look away during intense moments were burning into mine as I continued to undress.

Gazing down at my bare chest, she used one of her pretty manicured fingers to run small circles around one of my jet black nipples and areola and then the other. They responded quickly to her touch, erecting fully as she kissed my neck and earlobes.

“I love your complexion,” she purred. It reminds me of caramel.”

My cock was straining against the snugness of my panties and I felt a strong sense of relief when I worked them downward to let it spring out into the open air. I clasped the base tightly to pronounce the thick veins bulging around the shaft, extending its normal length.

“Oh God, hon. I’m so hard for you,” I breathed.

“I did that to you? ” she asked innocently.

“Mmmm, yes,” I gasped. “I’ve never been so turned on before.”

“Can I touch it?” she asked.

I was dizzy from the wave of excitement that surged through me when she asked that. “Go right ahead. “It’s all yours.”

For the first time in my life, I felt another person’s hand on my sex. She caressed my cock gently and clear streams of pre-come began to flow from its tip. “You can squeeze it harder if you want to,” I offered and she did.

“This is so strange, “she said, staring mesmerized at my cock as she stroked its hard length. “I’ve never touched another penis before. In fact, I never even thought I would.”

“Is this a problem for you, Devin?”

“Well, yes, sort of. I cant believe we’re doing this,” she replied. “But at the same time, I know that I love it.”

She kissed my lips again while firmly stroking my stiff cock. When our kiss broke, I moaned, “Oh, that feels so good, honey. Amazing.”

“I could make it feel better if you want.”

“How so?”

“I could sort of lick it a bit.”

“Would you really do that for me?”

“You have no idea how much I’d do for you.”

I pushed my panties down to my ankles and stepped out of them. Then I sat down on the bed with my high-heeled feet spread widely apart on the floor, my cock throbbing in an erotic dance between my open thighs. Devin sank to her knees and slipped between my legs to take me inside her mouth, gently licking just below the head of my staff, the most sensitive area. Then she went about giving me a full-fledged blow job. I savored every delicious detail of her going down on me; the softness of her hair on my thighs, the way she stared up at me, her soft hands gently caressing my smooth-shaven balls, the contrast of our skin tones.

“Am I doing this right? ” she asked between her downward sweeping oral caresses.

“You’ve got to be kidding,” I whimpered, lying back on the bed. “Can’t you tell?”

Every now and then, she’d pause to stare at my swollen cock, firmly stroking the shaft, her eyes glazed as my prick filled her field of vision. The peaches and cream complexion of her pretty face made my cock seem to appear darker than ever. She began licking me everywhere, from the base of my scrotum, across my ball-sack, and even at the aperture of my anal opening. She worked her tongue up along the underside of my shaft and teased my cock head with feather-like flicks and hot breath, then began sucking me in earnest, her head moving rapidly up and down, her talented mouth sending me racing toward orgasm.

Her lips reached further down my shaft as she worked one of her long, slender fingers inside my ass, sending me completely over the edge. At the moment of my climax, she pumped my shaft in her fist furiously, aiming the head directly at her face. Then began the maddening rapture of orgasmic contractions; great torrents of hot white seed racing from the tip of my spasming cock. The look on her face was one of pure amazement as my thick white come splashed against her lips, nose and chin. She gave me an erotic little surprise by scooping up my come as it rolled down her face and licking it up as if it were frosting on a spatula.

As I kept spending, she closed her mouth around me and stared up at me lustfully until I was completely finished. As I lay there, gasping for breath, she rose to her feet, the alabaster column of her cock completely stiff, the bulbous head engorged in an angry shade of red. I grasped her hot staff and playfully pulled her onto the bed next to me. I took each side of her beautiful face and kissed her deeply. We began rubbing our bodies together and I was hard again in no time flat. I reached down and impulsively slipped one of my fingers inside her virgin ass.

“Oh, God, I’ve been waiting for you to do that for so long, “she gasped. “Work it in and out of me, please.”

Her cock was oozing copious amounts of pre-come and when I suggested taking her ass with my cock, she responded with a bashful admission that shed fantasized about it, but had been too embarrassed to ask for it. Her eyes were luminous, her lips trembling as she breathed, “I want your cock inside me now. I want it.”

I thought about how lucky I was that my room was far down the hall from my parent’s master bedroom and that they never just barged in on me by surprise. I think that Devin was so excited, she never thought to ask about
it. As I reached into my nightstand drawer to find a small bottle of vaseline to lubricate my erection with, she perched herself on her hands and knees on the bed, raising her sexy little bottom high in the air. In the dim light, her ass looked so inviting, the shadows making its soft curves even more alluring. She reached back and spread her ass cheeks widely apart for me, displaying her tiny, wrinkled rosebud. I moved behind her with a trembling fist clasped tightly around the base of my throbbing hard on. She looked back at my swollen cock and a worried look came to her face.

“I’m not going to hurt you, Devin,” I whispered. She smiled back at me with a renewed sense of calm and assurance, a lock of hair dangling across her face prettily. “I’m not going to lie to you, though. Actually it might hurt at first.”

“I know, but I think I’m ready.”

I guided the head of my cock to her tiny rosette and pushed forward. It took several moments of patient care and a bit of lubricant before I managed to sink the entire length of my shaft inside. “If it hurts, let me know and I’ll stop.”

With my hands firmly grasping Devin’s hips, I began to move in and out of her with measured strokes, establishing a steady rhythm.

“Oh, God, I’m getting fucked! “she cried out, not in disbelief but in emphasis. I hadn’t imagined that she’d take to my penetration so quickly and with such unbridled enthusiasm. The inner muscles of her ass tightened around my pumping cock periodically, stretching my member out to its full length, drawing on it like a hot, hungry mouth. I reached beneath her and grasped her cock, which was every bit as hard as my own. As I shoved myself in and out of her, manipulating her erection in time with my thrusts, her cock felt like almost an extension of my own.

As much as I enjoyed taking Devin from behind, I had a sudden urge to have her lying beneath me on her back. I withdrew my cock just long enough for her to turn over. She spread her long, coltish legs high in the air in an abandoned offering of her tender opening. She let out a sharp gasp as I sank the head inside of her again. then she smiled up at me lustfully and began breathing heavily. Very slowly, I worked my way further, deeper inside her.

“Oh, yes,” she panted. “Give me all of your cock, please.” I probed inside balls deep, feeling her vise-like anal ring squeezing to keep the head of my tool from slipping from her tight orifice. As I fucked her faster and faster, with all the strength and endurance my body could muster, she yelped, shuddered and broke into a frenzy, bucking up against me. She wrapped her arms around my tightly and gasped, “Oh, God. I’m gonna come.”

Her cock erupted untouched, blasting a cascading offering of creamy white spurts that splattered across my stomach. Her ass muscles spasmed harder than before throughout her intense orgasm. I was soon about to experience for the first time the moment of exquisite bliss that accompanies release inside a hot tight ass. When I was unable to hold back any longer, I wrapped my arms tightly around her frame and came with a sharp cry and a series of violent shudders.

“I can feel you coming in me, Caramel, “she moaned. “Oh, I love this,” she mewled as I collapsed on top of her spent, sweaty form. Both of us completely exhausted, we cuddled quietly and drifted off into a deep slumber. The last thing I remember thinking about was that she’d given me a new name I might use for the rest of my life. That was pretty special to me.

Devin and I continued to meet as often as possible but after graduation, it was time to get ready for college and neither of us would be attending school near one another. I was to attend Northeastern University in Boston, MA and she was off to Louisiana State University. We stayed in touch by phone, snail mail and email but it wasn’t quite the same. What made things the most difficult was that we had no privacy at our dorms, not even for chat online much. We both had room mates to deal with and it always seemed that once one of us were free, the other was busy.

We looked forward to meeting during the holidays until her parents dropped the bomb that they were moving to Florida for an early retirement. Once it became obvious that it might be years before we got together again, we promised to stay in touch, and kept our hopes up about being together again and possibly exploring a long term relationship one out of college. For the next four years, we never stopped writing love letters to one another.

The Author of Caramel And Devin
welcomes your questions and comments:
caramel at ts dreamland dot com

BEWITCHED, BOTHERED AND BEWILDERED: Part One

Author: Lillia
View as a PDF

Krissy’s Note: Femdom is one of my favorite themes when it comes to CD/TV/TS fiction so this story by Lillia is one that I really enjoyed. How many of us Tgirls haven’t at one point or another gotten lost in our own fantasies… reliving that first moment we found that sliding on sexy panties turned us on…

Vivian flipped through his mum’s mail order catalogue, turning to his favourite bit – the lingerie section. She had asked him to choose something for his birthday, a new fishing rod perhaps, a couple of golfing irons to add to his set, or maybe even some new clothes.

The catalogue provided some welcome respite from the maths homework he should have been concentrating on. The funny thing was – it was the garments in which the sexy models posed, rather than their bodies that held him spellbound. How fantastic it would be to dress in something like that.

He drifted off into a salacious daydream – that of trying on several different exotic items. Wouldn’t it be really great to pose in front of a full-length mirror in them? He imagined imitating the stances and poses of the lovely models. Wow! How fantastic to have that job, getting to wear all that fabulous stuff, and getting paid for it. What must it be like to put on a pair of lace or satin panties, the gorgeous sensuous feel of the material around his bottom and against his cock? The thought stirred his JT into life.

Then there were the stockings and suspenders, the garter belts, and what about the wearing of a nice lacy bra, filling the cups with real breasts rather than padding. It didn’t seem quite right to cheat. Yeah, he knew even girls had to pad themselves out sometimes to achieve their desired shape, but he’d read somewhere about guys (and girls) these days, if they were so inclined, could have implants in whatever size they desired. There was really nothing to it apart from having the nerve – and of course the money – to go through with the procedure.

Some guys preferred the natural route… growing one’s own tits.

This involved a course of hormone injections to stimulate breast growth in the male gender. The results for some were quite astounding, achieving wonderfully natural-looking boobies, and for some an added enjoyment – and source of stimulation – the actual budding, the sprouting of little titties, watching them grow, and their continued monitoring into maturity and fruition, pubescent buds to full-blown milky bazookas was mind-blowing. Ultimately – he thought to himself – the thrill was watching oneself developing into an attractive young lady – plus… the added bonus of being able to tit oneself up occasionally, surely a fairly pleasant pastime in itself – kneading and squeezing and then teasing the nipples until they became hard and pointy. Oh boy, the very mouth-watering thought of it…

Vivian was fully hard now and a tad uncomfortable. To relieve some of the pressure he undid his fly and gave his burgeoning erection some air and much-needed liberty while he browsed the sexy pictures. He absent-mindedly stroked himself while reading. It was very pleasant. He’d just have to keep an ear out for the sound of his mother coming through from the kitchen. God, what if she caught him in this state of impropriety? Would she mistakenly assume that he was in the middle of a good old wank? And yet… would that presumptuous assumption be so far removed from the truth?

He must have been miles away because the next thing his mother was coming into the lounge, through the door and he had no time to zip up. In one quick, but awkward movement he’d covered himself with the glossy catalogue and hoped for the best. It was rather conspicuously open at the exotic ranges of underwear – crotchless panties, corsets, basques, girdles, garters, fishnet stockings… He felt his face become hot very quickly. There was nowhere to run, nowhere to hide.

His mother was an attractive woman; indeed, when she made the effort now and again she still looked pretty and at least ten years younger than her actual age. She cut a nice figure – good high tits and shapely bottom, the couple of extra chocolate pounds on the hips you could forgive. Everybody had a weakness. Many of Vivian’s mates had compared notes about their individual erotic fantasies involving his mum, Mrs Richardson. Of course, they never let on to Richardson junior.

“Have you found anything you like, Vivian?” said Mum, taking a seat beside him on the sofa.

Vivian knew his face must look like a traffic light on red at that moment. He felt flustered and had not even turned the page to something more appropriate – like sportswear, sports equipment or menswear.

“What’s this? Does my dear little boy have a thing for ladies undies? Or are you thinking of buying something for the girlfriend you don’t have yet but are thinking of acquiring?” She smiled teasingly, winked and nudged him.

“I was just getting to the right pages when you came in.”

“Oh I see. Here, give me the catalogue… I know the section you want. We’ll look together.”

“I can do it.” Vivian shifted awkwardly.

“Let me show you. You’ll be here all day at this rate.”

“No, Mum!” Vivian’s fingers tightened on the catalogue and kept it firmly pressed down on his lap.

“Give me the catalogue. What’s the matter… are you hiding something?”

“No! Please, Mum, let me do-”

And with one super-determined effort Vivian’s mother snatched away the catalogue from his ‘death-grip’ grasp. Something sprang to attention which naturally caught her undivided attention. Vivian’s hands flew to the rescue, covering the offending item as best he could. He wished he was somewhere else; far away… anywhere… anywhere away from here, away from his mother’s accusing eyes. He imagined lowering himself down into a nice deep hole and somebody putting a lid over the top.

“Oh, I see,” said his mother. “Your mind was obviously on other things.” Her eyes went from her son’s frantically shielding hands, to the pretty girls in the catalogue, and back again.

Vivian was speechless. Why didn’t she just go out of the room so he was able to salvage at least some dignity? But she didn’t go anywhere; she just sat there prolonging his discomfort, tormenting him it seemed.

“So this turns you on, does it? Girls in sexy underwear?” She tapped the page and then turned to the next page which had girls modelling even more exciting and revealing items. She held the catalogue up for him to see. “Which of these do you like best?”

Vivian looked away, squirming in his seat, wishing his erection would soften. But his naughty willy had no intention of letting him off so easily; in fact he was so hard now it was positively painful.

“Come on; tell Mummy which ones you like. Don’t be shy.”

“Mum, please..!”

“I’ve suspected for a while you know – that you were into this kind of thing. I know for instance, that you go through my underwear drawer from time to time. I don’t mind too much. In fact I’m quite flattered if anything, that you should want to play with my knickers. Do you ever try them on?”

Vivian shook his head in a shameful lie. He felt humiliated, but there was something thrilling about it too. It was as if he was being held prisoner but in a consensual, agreeable way, as if his cock would not allow him his freedom and dignity on the one hand, and on the other, the sceptre of his mother’s knowledge about his fetish paralysed him, kept him in his seat. The fact that she was fully aware of his present state of decorum (or rather – lack of it) only amplified his shame… and thus his enjoyment.

“All right, Vivian… I know how desperate your urge is. The lure of ladies underwear and the femininity it represents is a powerful force to some. She is a demanding mistress once she gets her long, sharp fingernails into you. It is pointless trying to fight it, believe me. It is better to embrace something you have no hope of defeating.

“I went through the same thing with your father when he was still around and I found it far easier going along with his desires and encouraging them rather than forcing him into denial. And so I’ll make it easy for you too. Here’s what we’ll do…”

Mrs Richardson angled her legs and turned towards her son, her skirt riding up to reveal an extra inch or two of sleek black stockinged thigh. Her knee bumped his leg. He could smell her warmth and perfume.

“You’re going to think I’m terrible, but… ” She smiled, folding down the corners of the page absent-mindedly. “I’d like to watch you do something…” She blinked and blushed. “You know…”

Vivian was confused. What was she getting to? “Watch me what?” he said. There was buzzing and ringing in his ears.

“Don’t make me spell it out.”

He stared at his mother’s nice breasts, the shadowy beginning of her cleavage visible in the ‘V’ of her skimpy black top. He wondered if she might be wearing a favourite item of his underneath – the lacy black bra he sometimes held to his nose, breathing the feminine odour of his mother while he played with himself. If she was wearing it now, how sexy it would be to slip his cock between her bunched titties, to feel the light graze of lace against his stretched foreskin. The sound of her voice brought him back to reality…

“I’d like to see you do it… see how much lovely spunk you make now you’re a big little boy. There, I’ve said it now. Are you shocked? If you do that for me I will treat you to a nice set of women’s underwear of your choosing for your 16th birthday. Perhaps you’d even like to model them for me? What do you think, Vivian?”

Vivian’s heart raced with confused anticipation. Did his mother really mean all that she was saying?

(…continued in Part Two…)

The Author of Bewitched, Bothered, and Bewildered: Part One
welcomes your questions and comments:
trevor at maytum.fsnet.co.uk

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