The Gigolo Chronicles Part 1 Katherine
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Conversations With Katherine free porn video
My boyfriend has some really weird friends and neighbors. One couple, who live just down the block from James, loved to throw themed parties. Costumes are always part of it, but during the party, you are supposed to stay in character. For example, last New Year's Eve they held a 1930's Prohibition-themed party. Everyone was a 1930's Gangster or Gun Moll. We had a Bonnie and Clyde, a John Dillinger and the Lady in Red . . . you get the idea.
James and I didn’t go the typical route and came in as a pair of Elliot Ness' Untouchables, complete with Tommy guns and axes to break up barrels of illegal liquor. It took some time to convince James not to go in the expected direction. My only issue with James is he does tend to be pretty conventional, in many things. When he realized I was going to dress as a Fed myself, he was more than a little put-out, especially when I added the pencil-thin mustache and wrapped my chest to look a bit more masculine.
I'm not overly endowed, but trying to look like a sexy gun moll wasn't going to happen. I liked Tom and Valerie, the hosts, a few of the other neighbors were a bit on the pushy side, especially after a few drinks. I mistakenly wore a two-piece to a neighborhood pool party and one of them was all too insistent and right in front of his wife. The host of that particular party had to ask him to leave. Luckily he wasn't drunk enough to stand up to him. I heard the asshole and his wife split a while back, so hopefully, he won't be there. But I decided to keep things low key for any future pool parties.
When I said I had just one issue with James, I did mean it. I really like the guy and in many ways I love him. But we were never going to be more than boyfriend and girlfriend and had been for the past two years. It seemed odd to many of our friends, but it worked perfectly for us. We enjoyed many of the same things and had a great time together. The sex was good, even if there he was a little conventional, but he was usually willing to try a few new things. Nothing outrageous, but different.
So back to the party invite, just what was the theme for this party? Sex! No, not an orgy, but just to dress sexy and act a bit more . . . well . . . slutty. At first, I was a little put-off. I mean if that one asshole was going to be there, I certainly didn't want to dress like a hooker! Of course, that was James' first reaction. Him as a pimp and me as his hooker/girlfriend. I decided I wanted to change things up again and hopefully not walk around with a target on my ass to be patted at every turn or worse — getting hit on by any other drunk husband or boyfriend. It took a while but I finally figured out an alternative, but it took over a week to talk James into it. It was pretty out there, and I was surprised how much I enjoyed it as I tried it all on! Jessie’s, the adult boutique off Main, made a bundle off of me for this party. Two of the girls who worked there helped me get it all together and even helped me dress at the shop to try it all on. As I was leaving, Natalie, the clerk who rang up the sale, hugged me and offered to come to my house to help me get dressed up, any time. I was both surprised and a little flattered.
I knew our outfits were going to have an impact, but even I was surprised at how the conversation simply ceased as we walked in. From experience, I knew it was a party for adults only and the kids would be off having their own little get together at another house, so James and I went all out. The best part is no one could tell it was us just yet. My leather hood hid my hair and the mask covered most of my face. I knew once I spoke they would figure it out, so James and I decided to not speak for a long as possible.
As you might have guessed, my outfit was that of a leather-fetish dominatrix. The form-fitting black leather bodysuit, the nearly knee-high boots, even the fingerless gloves were a matte-black. My accessories included a chain belt with a curled-up whip, a leather collar, and a set of handcuffs hooked to it, and some decorative silver zippers and accents. My upper chest was open and the tight leather actually gave me more cleavage than normal. The shoulders were bare, showing more skin. The legs had several strategically placed slits so I would show a lot of leg as I moved around. There was one more thing and James almost freaked when he saw it, but it made the costume as intimidating as I wanted. An 8-inch black, life-like toy, complete with black harness. I rigged the harness so it didn't stick out perfectly straight, but hung down a little, like it wasn't erect, but with a tightening of two straps, it could be. When I looked at myself in the mirror I loved it and for just a second thought about how much Natalie liked it!
When I walked out of the bedroom with it on, James' eyes grew two sizes. But he didn't argue, for a change! Maybe the outfit was even more intimidating than I realized. I watched him dress and while I wanted him to get into the game and go as a submissive slave, I couldn't make that sale. I did get him to put on a very sexy plastic outfit, made of PVC. It was fun treating his skin with lotion to get him into it. While he didn't look like a slave, he was not the dominant one of our pairing. His outfit was also black, but PVC shiny! The hood with a built-in mask, a tight-fitting shirt, pants, and lace-up sandals completed the look. There were several strategically placed buckles that I told him were for accessories he didn't need. What I forgot to tell him was that the accessories were on the unusual side and I did buy a couple. But the ball-gag wasn't going to fly, so I didn't even try. I also had a waist chain with two built-in handcuffs that I was going to try and use when I was working on him to be a submissive, but he didn't go for it, so I just left them in my car.
What I loved about his outfit was just how form-fitting it was. James is in pretty good shape and the shirt showed it off. The pants were also form-fitting, so tight you could tell what religion he was, even soft. I don't think he realized just how tight it looked, but I sure did and I loved it. From behind his ass was perfection! He tried it with underwear, but it wrecked it. Without underwear, it was nearly obscene . . . I loved it. For a second I was tempted to stay in, but figured we would be playing later! Time to scare the shit out of his neighbors.
Like I said, walking into the house, all conversation stopped. Valerie greeted us, and I took charge and shook her hand, but didn't say anything. She caught right on and grinned. She hugged me and whispered, "You two are going to drive some folks insane!"
I smiled and she paused, leaning in again. "Don't smile, Katherine, it gave you away. You look fucking fabulous and James looks absolutely edible! He might be fighting some of the women off by the end of the evening." I hugged her tight, in acknowledgment, but still didn't say anything. I vowed to keep a stern, domineering look on my face until identities were revealed.
I was right, most of the folks went toward slutty rather than sexy. There were a couple of exceptions. Donna was there, it was impossible to miss her hair, even wearing a mask. She was not with her ex, thank goodness, but a smaller, Asian, girl. The two of them looked like a couple. Good for them, she had to be able to do better than Frank! I recognized a few more, mostly the ones who didn't bother with a mask. There were quite a few others whose identity was well hidden. What I loved was the attention from everyone! While they didn't stare, it was nearly palpable! You could feel the eyes and in a few cases the desire! I expected intimidating, but not the feeling of being both sexy and powerful!
The party at that point was pretty normal. Food, drink, some dancing, and what turned out to be the hardest thing - no pun intended - not talking. Dancing was also surprisingly difficult. A few of the guys tried to get me on the dance floor, but there was one person who refused to take no for an answer and it was a she. She was shorter than I was and in a very sexy outfit. Do you remember the show 'Firefly'? She was dressed in a costume similar to Inara, the 'companion'. It showed a lot of Japanese styling and was incredibly sexy without showing much skin. She didn't ask, but just held out her hand and practically dared me to say no, which I simply couldn't bring myself to do so.
So I let her lead me to the dance floor, actually on the back patio where half of the party was. She took me in her arms and led. For a moment I was off-center. I loved dancing, especially to such a nice slow song, but the height difference was disconcerting. I was used to be led on the floor, but I was also used to being shorter than my partner. When she pulled me close, there was a clear spot around us as folks watched. I know it wasn't simply because it was two ladies dancing, because Donna and her partner were frequently on the floor, as were several others, including Valarie and a few different women. But there was something different when we danced and I think people felt it more than saw it. I know she felt the toy and at one point she reached a hand between us to reposition it to a more comfortable spot. I am sure you could guess where that was. We kept it between us, but I felt her breath change and realize she was getting turned on, which was getting to me as well. When the song ended, she kissed me on the cheek and thanked me in a low, sexy voice. I had to sit down after that and cool off!
Slowly the masks were taken off as people were identified. Finally, it was down to three of us. The majority of the party-goers had gathered in the living room and the three of us were in the center. It was James and I and one other lady, of course, the Inara-dressed woman. Valerie hosted the unveiling. While there wasn't an official contest, Valerie declared ‘Inara’ the winner. She explained that she had realized who James and I were much earlier, but left it to someone else to figure it out. But even she hadn't figured out who Inara was. James took off his hood and everyone applauded. When I took off my mask and lowered the hood, my hair came tumbling out. I had it colored black to match the outfit and it looked pretty good, even after being trapped all evening. Now it was the Lady's turn.
She walked around the center of the room briefly, offering a tantalizing tease and still no one could figure it out. There were several guesses.
She stood in front of me and asked me to do the honors in a quiet voice. As I took her mask off, even I was surprised. She had also colored her hair, but once I saw the small elfin face I realized it was Gem. I also figured out why no one had recognized her. I don't think anyone had seen Gem wearing anything but torn jeans, the occasional bathing suit - always a one-piece - or running shorts when she was jogging in the neighborhood. I know I had never seen her all dressed up and she looked amazing!
She twirled around and received her acknowledgment from the group. There were hugs all around, and even a few for me from folks. I avoided the known lechers, which was easier seeing all the faces. What started being funny was watching James and how much attention he was getting. He got dragged out to the dance floor by two ladies and I knew he was enjoying himself because there was no way to hide it in those pants. He started getting a great deal of attention and when he looked at me helplessly, I just shrugged and smiled at him. Across the room Gem was just sitting there, sipping some wine. She seemed in a little bubble, no one was talking to her right then and she was simply looking at me. I had trouble looking away for some reason.
At one point she slid her gaze toward the patio door and back to me. I thought she wanted to dance again and I swallowed nervously. I nodded and she headed out into the backyard. I waited a few moments and went out there myself. I didn't see her right away. I had expected her on the dance floor. Then I caught a flash of color off to the side, near the bushes and trees bordering Valerie and Tom from their neighbor. It was her dress and it disappeared between two hedges. When I got there, I found a short passageway of hedges, overhung by tree branches. She was standing next to a tree in a quiet spot and even had a small table and a couple of chairs.
I went up to her and she smiled at me. "I really enjoyed the dance," she said softly. Before I could answer, she reached out and grasped my toy. When she pushed it against me I realized that I had enjoyed the dance even more than I realized. I looked around nervously for a minute.
"It's okay, Val and I planned this little bit of privacy. We sometimes have coffee out here and appreciate the quiet." At that point, I remembered than Gem was the next house. While my brain was engaged dredging up that fact, she pulled me even closer, almost like we were dancing again. "I wanted to do this so badly after we danced," she then kissed me.
Her lips were so soft, softer than any I had ever kissed. She wasn't forceful, but her lips slowly parted and her tongue ventured forth almost shyly. My brain wasn't engaged, but something else certainly was. I opened my lips a bit and touched my tongue to hers. We melted against each other. Don't get the wrong idea, I was straight! But I don't think anyone could remain straight in such a situation. I think I started running on a sexual high the moment I decided to dress in this costume. The small pass from Natalie was part of it, as was James's costume. Everything that had happened was a turn-on, even the attention at the party! When Gem's lips touched mine, I was helpless. It felt so perfect!
She pulled back and tugged at a few things on her costume. The large sash at her waist was holding everything together. The dress parted and she shook off the outer layer and then she pulled me in for another kiss. This time her hands were roaming my leather and my hands realized she was practically in little more than a shift. I pulled it up and soon had my hands on her naked waist. I could feel her smiling in the kiss as her soft lips firmed up. She started pulling a little on my toy and I did something very challenging, I let go of her and tightened two straps. My cock, there was no other word for it anymore, but my cock was sticking straight out. Gem turned and grasped a low branch and stuck out her ass, holding up her shift, I could see her bright white skin through the leave-filtered lights. The invitation was one I was physically and emotionally unable to refuse. I stepped behind her and rubbed the tip up and down.
Her low groan was thrilling. I could picture the wet tip as I felt for the right spot and slowly sunk it into her. She was more than turned on because I slid right in. She pushed back and grabbed the branch with two hands. It felt so strange to me! I wasn't a stranger to toys, but I was always on the receiving end. The tightness of the leather made me feel a sharp pressure right on my clit with each push. I felt a bit empty, but that pressure felt good, exceptionally good. Gem moaned again, very low. I knew she was trying to not get anyone's attention, but I'm not sure I cared as much. I held her hips as we started getting faster and faster. Just as we started getting very close, there was a movement of the bushes. Gem reacted first, almost like she was primed for it. I was too confused by the sudden change to even think. She pulled off and grabbed her overdress and sash, then pulled me deeper in the bushes. She stayed low, I was still in so much matte-black it would have taken someone with a flashlight to realize I was there. Gem stayed next to me but stopped me from moving and rustling the bushes. I heard them come to the cleared area, then I heard the voices.
James was easy to identify. Someone must have gotten his attention the way Gem had gotten mine. Part of me should have felt something more, but I really couldn't blame him. After all, I was doing the same thing. Gem slowly stood up and we both look back, moving slowly to avoid any attention. I could see James sit down on one of the armless chairs. The woman with him stripped off her pants and sat upon the table. Her voice was nearly as easy to make out as James', even with her stage whisper, it was Valerie. She pulled his face down and without even a token protest, he was going down on her. Gem leaned against me and touched my toy, slowly grinding it against me. Val wasn't as quiet as Gem, but she wasn't too loud. We were probably the only ones who could hear her and her semi-quiet mews were hot! Gem's motion with the toy just made it worse for me. I was as turned on as I had ever been in my life, I think!
In minutes we could see Val shake in a small orgasm. James stood up and started tugging at his PVC. I nearly laughed because it was really hard to get him into it, it must have been nearly impossible to get out of it quickly. Val stayed on the table while he struggled. Her legs splayed while she played with herself. James finally succeeded getting his cock out and he wasted no time, he just started fucking the hell out of her. Gem reached up and slowly pulled my head down. I thought she wanted a kiss, but instead, she whispered, "Slowly look to the right."
I looked back up and slowly examined the area to my right and I nearly jumped and gave the whole thing away. Tom was standing there. In a moment I realized he was doing more than just standing there, he was jerking off. Wow! I couldn't help but wonder how well James had known them before tonight but didn't care that much, which surprised me.
I turned my face back to the main action and realized it was going to be over all too soon. James was way too excited to hold on for long. I guess he got as turned on all night, just like I had. Val slowed him down and finally stopped him. He was still buried inside her and was catching his breath when he felt something behind him.
Tom had joined them and pressed up against James. He tensed up and there was a quick whispering, sounding slightly like an argument. I was pretty sure this was something new for James, but surprisingly Tom seemed to be an old hand. I watched as Tom pulled James' pants further down, baring his ass. Val was making encouraging noises and . . . well, can we say they educated me that night? It took a while, but Tom eventually got into James. He must have been a virgin back there because it took a long time, lucky for James Tom was patient. As soon as he started, Val seemed to be a near-constant state of orgasm. Every move Tom made, she felt through James.
Gem pulled me down lower. "Care to watch any more or should we leave?"
"They might see us?"
"If we stay low and move slow, we can give them some privacy. We can go to my house."
We snuck out of the hedges and entered her house from the lower patio door. On the way, we heard a few cries from the bushes and hoped no one would bust them. Gem kept her lights off and took me into heaven, but heaven I am talking about is her bedroom. It was huge and beautifully decorated! I thought her house was a 4-bedroom split level, but she must have merged two or three of them into one. She led me to the bed and was sat together, not doing anything.
"Are you okay?"
"Fine, why?"
"Well if that had been my boyfriend, I might not be so fine."
I realized where she was going and shrugged.
"Yea, he's my boyfriend, but look at what I was doing before they rudely interrupted us."
"God, I was hoping you would feel that way." She stood up and lost all her clothes. She was slim, as anyone who looked at her would know, but she had a nice slim shape to her. I started to tug at my leather and she stopped me. "Not yet." She pushed me back on the bed, straddling me and took my toy back into her. Like this, I could feel even more, with her weight coming down on me. She looked me right in the eye and started fucking herself on my cock. It was an experience, and her weight coming down pushing against me. It wasn't quite the same as masturbation, but then the view was much better than anything my imagination could dream up.
It was fascinating watching her climb higher and higher, her movements getting harder and slightly less coordinated. I watched her cum and it was such a turn on. She kept going, right through her orgasm and by the time she came again, I was right with her. I had to close my eyes, for the first time not watching her. I couldn't help it, my orgasm took me someplace else, someplace I hadn't visited before. When we were both done, she curled up on top of me, with my toy still inside her. My arms around her, holding her close.
She smiled at me, "So, do you want to go back to the party?"
"Oh hell no!"
"Good answer. But I think we can do without all the leather, as delightful as it is."
"I don't exactly have anything else to wear."
"Oh, I think we dispense with that till morning. Then I'm sure I can scrounge up something or other."
She helped me strip, and I don't I have ever had so much fun just taking clothes off. She was playful and very physical. By the time I was naked, I was horny all over again. I got the impression she was much more experienced with women than I certainly was. Since she was my first female lover that should go without saying. Kissing a couple of other pre-teen girls when we were all curious as hell about boys doesn't count.
We made gentle love for the rest of the evening. The mechanics of it shouldn't have been a surprise, since there was only one thing missing, but not what you might think. What was different was the . . . patience. At no point was she harsh or demanding. She was patient in what she did and also what she wanted me to do. It was . . . hard to describe. It simply felt the way sex should always be, exhilarating and yet calming at the same time. We fell asleep in each other's arms, perfectly content.
Waking up the next morning was a slow, languid affair. The light coming in gave me a new appreciation of Gem's bedroom. It was huge! High cathedral ceiling, the windows were eight feet above the floor. I realized that this bedroom was the original living room for this style of house. As I looked around, I realized that it was more than a bedroom. There was a nice sitting area, with an entertainment unit. Half a level up was what looked like a nice kitchen, completely open to the bedroom.
"There are privacy screens I can lower if need be." Gem had woken up and watching me look around.
"This room is incredible."
"Well, I like it. But right now, I need coffee. How about you?"
"First the loo, then I can restock my system with caffeine."
Gem laughed and pointed to the left. "Right there, then come on upstairs. There should be a robe hanging there that should fit."
"Your girlfriend?"
"No, just one I bought that was too big. I do like to snuggle in it in front of my fireplace on chilly nights. You don't have to wear it, you can stay naked." She pushed off the sheet. "I plan on it."
We shared coffee on her kitchen table, naked! It felt comfortable and the feeling of open space made the space seem very comfortable.
We didn't talk, which seemed a little strange, but I think it was a hold-over from last night. We felt comfortable with each other.
She rummaged through a drawer and came up with a cell. "You might need to call James. He could have been worried about you."
I nodded. That thought was circulating in my head someplace, but I didn't know how to bring it up. All I had on me was the outfit I wore last night, no license, no cell phone, and no car keys . . . not like me at all.
"Thanks!"
"You can call me Gem or you can call me 'lover' if you want. But if you call me ‘Honey’ we are going to have words,” She said with a smile. “But I have to ask, are you okay with last night? I didn't realize until later you've never been with a woman."
Looking closer I realized that there was a little nervousness in her movements. I would like to say I knew her well enough to tell. But to be honest, I didn't. James mentioned her a few times and I had run into her in the neighborhood and, of course, at earlier parties. But I didn't know her. I looked at her in a way I hoped was reassuring. "Gem, love, I am fine. I am better than fine. Last night certainly didn't go as planned, but it went much better than planned."
"You had a plan?"
I laughed. "Well, after the party of fucking James' brains out. I didn't realize how turned on that outfit and all the attention was going to get me."
"Sorry to wreck your plans!"
"If you try and apologize for last night, I will put my leather back on and spank you!"
"I might like that," Gem said encouragingly.
"I might as well! I tried to get James to go as a submissive slave, but that wasn't going to happen."
"He looked pretty submissive last night."
I remembered how we last saw him. His cock in Val and her husband's in James. "I know. That wasn't like the James I know at all. Do Valerie and Tom do stuff like that often?"
"Sometimes. I stay out of their love life. The only thing I would say is they never force anyone, but they can be persuasive. I like them both very much, and I think James had his hands full last night."
"I don't think it was his hands!" I said, setting us both to laughing.
I called James and the first thing he did was apologize.
"I'm sorry. We lost track of each other," James said earnestly.
"It's okay, James. Are you home?"
"Not yet. I crashed at Val's. I think I overindulged."
I thought about telling I knew better, but it was no longer any of my business. I still like, and even love James, but I think we are permanently in the friend zone now.
"Okay, call me back at this number when you get home. All I have is leather."
We said goodbye. It was funny, James never even asked where I was. Maybe he felt what I was feeling.
Was I in love with Gem? Not yet, but it was possible. I don't know what the future for us holds, but I hope it involves lots of patient and comforting sex!
Alessandra
- 08.06.2022
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