I excused myself for a minute and returned with a long, black negligee, which I asked him to model for me. Daniel left on his bra, panties, hosiery, and heels, and then slipped the floor-length gown over his head. It fit him nicely, even though I could see his cock bulging beneath the gown. I caressed his dick as we sat together on the couch. Between nuzzles and light kisses on his face and neck, Daniel shared details about his life. I found out that he was twenty-three and had just gotten a job teaching. He was exactly the type of “girl” I was looking for.
Daniel spent the night in my bed dressed as Danielle. I hiked up his negligee and pulled down his panties, climbing aboard his deliciously male cock as I enjoyed the feminine frills adorning his slender frame. I rode his stiff dick until I was satisfied, and he came in my quivering sex. Then I moved upward and straddled his mouth, telling him to drink down our combined juices. He did so willingly, tonguing me to yet another orgasm.
In the morning, I asked Daniel if I could dress him up for a daylong outing and another party that evening. Of course, he was ecstatic. After another round of lovemaking, I spent the rest of the morning having him try on dresses. My walk-in closet contains numerous outfits in various sizes. Danielle is a pleasantly shaped size twelve, at five-foot-eight, and her feet are only a size ten. When I was finished with her, she was a gorgeous lady ready for a day on the town, wearing a white sundress, white slip, panties, bra, heels, and beige pantyhose. I refreshed her makeup, and then we were off. I treated Danielle to lunch, did some shopping in the afternoon, and then we had dinner at a nightclub. Danielle was totally at ease, which I took as a good sign.
For the next few months, Daniel and I went out on “dates.” I told him that his cross-dressing was a turn-on and that I enjoyed his soft, feminine side. During our time together, I created a portfolio of pictures of every Friday-night date transformation and outing. I loved having him as my own personal plaything, and I tutored him on how to behave in the most feminine way possible. He listened to every bit of my advice, eagerly taking it all in. Our relationship had taken on a distinct domme/sub flavor, and I was ready to take things to the next level.
When winter recess was approaching and Daniel didn’t have to work, I invited him to spend that time with me at my place. Since he was a good friend and very comfortable around me, I decided I was going to reveal my business to him and tell him I wanted him to work for me, so I set up a dinner party at a local hotel’s restaurant to spring my surprise.
Danielle showed up for dinner, dressed in a floor-length red gown. She was absolutely delicious-looking. After we were seated, one of my best clients joined us. Rich has a preference for young cross-dressers, and I knew he’d love Danielle. I introduced the two and told Danielle to relax and enjoy the evening. After our meal, Rich took her onto the dance floor, where they seemed to be getting along famously. Once they came back to the table and Rich excused himself to go to the men’s room, I explained my business and told her that Rich was a special client of mine and that I expected her to show him a nice time and spend the weekend with him. Danielle seemed shocked by my suggestion and started to protest weakly, but I could tell from her swelling cock and the blush on her cheeks that she was really turned on by me telling her to have sex with a stranger—and a man no less! I even went so far as to threaten to show off my photo album of Danielle’s sexiest looks to everyone she knew if she didn’t do what I said. Even though she knew I was playing and wouldn’t actually do that to her, I could tell that pretending to be blackmailed made her really excited.
I explained to Danielle that I would provide all of her feminine clothing, makeup, and wigs for her “dates,” and that if she worked for me, she agreed to sleep with whomever I deemed suitable. She agreed that she would do whatever I said, which thrilled me beyond belief.
When Rich returned to the table, I explained that Danielle was a new “girl,” and that he needed to be gentle with her because she’d never had sex with a man. Prior to dinner, I made sure that their room was well stocked with all of the female trappings that Danielle might need for their weekend together. Then I left the two of them alone, so they could have some privacy.
I drove home with thoughts of Rich and Danielle filling my head. The idea of the two of them having sex all weekend completely turned me on. The fact that Danielle was giving up her “virginity” to Rich on my orders made my pussy drip. Every time I stopped at a red light, I had my hand down my panties, frantically fingering my clit every second I could. At the very last traffic light, I brought myself over the edge, moaning loudly as I bucked in my seat. I took a little too long to come, though, because I was shocked out of my postorgasmic reverie by the driver behind me leaning on his car horn after the light had changed to green.
On Monday morning, I met with Rich to confirm that he was satisfied with my new girl. He assured me that Danielle had shown him a good time and profusely thanked me for providing him with a virgin. I assured him that Danielle would be available to him any time he was in town.
Danielle and I have continued to have a sexual relationship, and she has fully accepted her role as my “employee.” I think she is really enjoying her new career as a high-class TV escort!
—Ms. Lola D., Miami, Florida
Couple Experiences the Joy of Spanking on a Kinky Cruise
For our third wedding anniversary, my husband and I decided to go on a cruise. I was very busy at work, so I let Brett investigate our options. What he eventually came up with surprised me: a “kinky” cruise in the Caribbean. “But we don’t do… that stuff,” I said, gesturing toward the brochure photos of women and men in bondage and getting spanked.
“Well, I was thinking maybe we could learn a little more about it. Participation isn’t required, and there’ll also be some porn stars there to talk to, as well as kinky people who really know what they’re doing. Plus, there’ll be sun and good food, and all the materials say we can just watch the action if we want to. What do you think?”
The more I considered it, the more intrigued I became. I would never have brought up the subject, but deep down I wanted to know what it felt like to bend over and have a firm hand connect with my bottom, and if Brett were interested, I wanted to watch him get spanked. I wasn’t sure yet if I wanted to spank him, or whether I was even up to the task of topping someone.
“Well, I think we should keep exploring our options,” I said as I walked over to him, very aware of his prominent erection. I touched his cock, but I didn’t make a move to undo his pants just yet. I asked him what he wanted to try if we went on this cruise.
“Spanking, I think,” he said, and I felt his cock jerk against my hand. I made him tell me more as I sank to my knees, and then unzipped his pants and swallowed his cock. I thought about him bending over and getting spanked by a stern-looking woman, then about him taking me over his lap and giving my bottom the same treatment. When Brett came in my mouth, letting out a cry of excitement, I knew that this was the vacation for us.
When we boarded the ship, I instantly relaxed. Brett was right; there was nothing to worry about. Everyone in attendance was friendly and normal-looking, wearing bathing suits and flip-flops, and sipping fruity drinks. The women didn’t look like scary dominatrices with whips—at least, not yet!
On the first day, we mingled with our fellow vacationers, enjoying the sun, fresh air, and sense of adventure. At one point, I started talking to a woman my age, Felice, and she told me that she had only recently begun to explore what she called “the scene.” She was open to all my questions and answered them honestly, telling me that she was mostly a sub, meaning she liked to get spanked, but occasionally she ordered her husband, Raymond, around.
There were lots of introductory classes being offered, on everything from rope bondage to hot wax to spanking to how to be a top or a bottom. I told Brett that I didn’t care what classes we went to as long as we could go together; I was still too intimidated to fly solo, even though everyone seemed nice.
“What
about the spanking demo?” he asked. From his earlier comment and the gleam in his eyes, I knew that the class wasn’t plucked randomly from the cruise’s offerings.
“Sure,” I said, then pulled him close for a kiss. I liked that we were among people who wouldn’t mind a public display of affection. After all, ladies were going topless, and there were even people being led around by leashes! Somehow, these sunny, smiley people made it seem totally normally for us to be setting sail on a beautiful day while the sounds of kissing, spanking, and flogging filled the air.
We entered the spanking presentation and found that almost all the seats were taken. The only ones still available were at the front. Normally, I like to sit in the back of any room—or the middle if we’re at the movies. The front row is never my cup of tea, but we had no choice. It was either that or we’d have to attend another workshop. I could tell Brett would’ve been disappointed if we’d passed it up, so I bravely walked toward the front. The demo hadn’t started yet, so I hoped we could be inconspicuous.
For some reason, I had assumed there would be a woman teaching the class, but instead, there was a man—and a hot one at that! I felt a tingling in my pussy when he paused to stare at me. Then he introduced himself to everyone. His name was Tom, and he said he’d been into spanking for more than twenty years! He went over some basics, including the common reasons why people like to spank and be spanked, and then he showed us some implements. The items ranged from an average hairbrush, a ruler, and a spatula, to handcrafted paddles and whips. Then he asked for a volunteer for his demo.
Brett whispered that I should raise my hand, but I wasn’t sure I wanted everyone in the room to see my virgin bottom get spanked for the first time! Plenty of other hands were raised, with lots of joking, smirking, and grinning by those in attendance. Tom looked all around the room, as if making his decision very carefully, and then he pointed at me. “Would you like to come up?” he asked. His kind eyes seemed to read my excitement and uncertainty all at once, and somehow I felt I could trust him. I looked at Brett, who simply gave me a thumbs-up as the crowd applauded and offered encouragement.
After that, I couldn’t really refuse. Besides, I was too intrigued to say no. What if I didn’t get another chance to do something like this? Tom spoke quietly to me, asking my name and whether I was a newbie. I told him I had fantasized about spanking but had never tried it, and I wasn’t even sure if I was a top, a bottom, a switch, or none of the above. “That’s okay,” he said in a soothing voice, and then asked if I’d feel comfortable with him flipping up my skirt. I was nervous, sure, and blushing even, but I said yes. I wanted to know what a real spanking would feel like. Tom put me at ease by assuring me that if I didn’t like what he was doing, I could stop him at any time.
When I told him I was ready to start, Tom had me bend over a padded spanking bench. I kept my eyes shut while he exposed my panty-covered ass, stroked my butt, and then pointed out things to the crowd, like where my “sweet spot” was. It was a new sensation for me, being on display like that, but I couldn’t really focus on it because I was eager to finally get spanked. The more I thought about it, the more I had a feeling I might like it, especially since Tom was so sexy. Then he leaned down and asked me if I was ready to be punished. “Yes,” I whispered, amazed at how intimate a moment it was even in front of all those people.
Then the spanking began. I shut my eyes and felt his hand connect with my right butt cheek, then my left. The sensations made me catch my breath, made my heart beat faster, and caused my pussy to twinge as he swatted me over and over. He then suddenly stopped to explain to the crowd that he had been warming me up and that I could now tolerate harder blows. Then Tom really started in, using his hand to spank my entire ass as well as my upper thighs. At first, it didn’t seem like he was doing it that hard, because the swats were spread out, but the more he slapped me, the more tender my skin became. But when his hand repeatedly landed in the same spot on already-spanked skin, I finally felt the beauty of true masochism.
Tom had explained that some people process this kind of pain as erotic, and some don’t. I was one of the former, and I felt as turned on as when Brett fucks me good and hard. In fact, I hoped that after this demo my husband and I could retire to our room so he could do me doggie-style.
After the hand-spanking, Tom started showing the crowd how to use various implements. Some felt silly, like the spatula, but the hairbrush—though small—was sturdy and managed to heat up my backside really fast. When Tom got to the paddle, he teased me at first by bringing it just up to the surface of my skin, then stopping. I knew my panties were wet, but I didn’t care.
I wondered what Brett was thinking. Did he like seeing me in such a submissive posture? Did he want to spank me or get spanked himself? I kept my eyes shut as Tom used every toy in his arsenal, finishing up by rubbing his hands together and then delivering a few final very hard, warm smacks. My bottom was tingling as Tom helped me up, and I sat down gingerly on my chair. I was in a daze for the rest of the demo.
When the class was over, several people complimented me on how well I’d taken my spanking, and a few men told Brett that if he ever wanted to share me, they were more than willing to paddle my bottom. Those statements made me blush but didn’t offend me. This was a different kind of environment from our everyday life. Their words were compliments, not perverted come-ons. We went back to our room right away, and Brett told me his dick had been hard the whole time I’d been on display. “Can I try it?” he asked, his voice soft, as if expecting me to say I’d already reached my spanking quota for the day.
“Yes,” I said, because even though my ass was still warm, I wanted the man I loved to spank me. He stripped down to his boxers, while I got totally naked. He played with my breasts for a few minutes, sucking my nipples, before spreading me across his lap.
“Here’s the sweet spot,” he said, and then smacked me at the center of my ass cheeks. “How does that feel, Sam?”
“Good. Very good. Keep going,” I said, already starting to pant with arousal. And he did, quickly getting the hang of it as he went. There were a few errant blows that didn’t land as forcefully as he’d have liked or that were too far from the center of my ass to feel especially arousing, but most of them were spot-on. When he paused, I told him how wet he’d made me. He stroked his fingers along my slit and then let out a whistle.
“Ten more,” he said in an unusually deep voice. Those ten were extra-hard, harder than even Tom had spanked me. When he was finished, I really knew what being a spankee was like—and that I was a convert. Then he did indeed bend me over the bed and fuck me, while fondling my warm, pink cheeks. I came soon after the first thrust, blissfully happy, and he erupted inside me shortly afterward, leaving my pussy dripping with cream. Before we took a nap, Brett insisted on spanking me with my hairbrush, then taking a photo of my ass to remember the moment. The next day, he let me spank him, and during the rest of the cruise, we found other people to spank us!
Since then, we’ve even joined a spanking club where we can further explore our fetish, and we have another kinky anniversary cruise planned for next year. Who knows what we’ll discover about ourselves on that trip!
—Ms. Samantha L., Boulder, Colorado
Pony Girl’s Trainer Puts Her Through Her Paces to Help Break in Her Fancy New Gear
My girlfriend, Liv, loves playing all my silly sex games, and pony play is one of her favorites. It’s one of our most exciting scenarios, and we have dozens of props to help us in our equine-themed sex play. I have a butt plug that has a long tail made of synthetic hair, and when I wear it, it looks like I have a tail of my own, like a real pony. We also have a gag that’s like a horse’s bit—a latex-coated metal bar to chomp on rather than a rubber ball—and a number of crops to keep me in line.
I love everything about being a pony that’s under the control of my trainer—especially when she whips me. There’s a powerful thrill in getting to be someone, or something, else for a
few hours. But one of my favorite things is getting dressed up with my pretty pony props and showing off, even if it’s only for one person. Each time we add a new piece of tack to our collection, Liv and I act out a scene, so I can decide if the new toy works with my pony persona.
The most recent additions to our pony-play props are a plumed headband and a bright-red leather body harness that cinches around my waist like a real pony’s saddle does. And when we brought home our newest toys, we had to break them all in right away, of course.
“You’re going to be such a pretty pony girl!” Liv cooed as she watched me slather lube on my ponytail butt plug. That’s the only accessory I’m allowed to don by myself, because, as Liv likes to remind me, real ponies can’t put on their own equipment.
As I prepared my plug, Liv changed, too, putting on a sexy pair of fringed bikini panties and a matching bra, plus her favorite pair of cowboy boots and a cowboy hat left over from an old Halloween costume; she insisted it was necessary to get into character. Once she was properly attired—and my butt plug was firmly in place, with its tail hanging down my ass like a real one would—we were ready to play.
I got on my hands and knees and allowed Liv to finish getting me ready. She started by brushing my mane and tail—“No one would take out their pony without grooming her first,” she’d stated the first time we’d played—and the slight tugging of my hair as she worked through tangles and knots made my pussy spasm. My spine tingled as she brushed my hair, which it did even when we weren’t in pony-play mode, but when she brushed my tail, I really went wild. She held the base of the plug so it wouldn’t get pulled out if there was a really big knot, but every brush stroke caused subtle movements, and my sphincter clenched tight around the silicone shaft each time she tried to work through a few tangled strands. That wasn’t exactly a problem, though, and the pressure from each unexpected tug had me worked up and ready for more, long before Liv had finished grooming me.
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