A Fantasy with Lisa

I met Lisa for the first time just after finishing a workout at the local gym. Over the next few weeks we ran into each other on a regular basis and ended up going to out for a few pints. Spending time together eventually put us in bed together and we decided out relationship was best left as a friends with benefits situation. Over time we discussed each other’s fantasies and fetishes and did our best to fulfill them. It started with her admitting to her desire to give head while driving around in the city. I mentioned my longing to be tied up and teased and after a drive to her place I found myself tied to her bed for two and a half hours of torturous fun.

It was soon after that night that I told her about my biggest fantasy, to be dressed in drag and play the female for an evening. I saw the spark in her eye as the possibilities ran through her head. She asked if I had ever been in drag before (which I had once), and if I owned and female garments (I didn’t at the time), but to my disappointment after that night nothing else about it was mentioned.

For weeks after that she subtly pried for more info about my past history and what I was open to, finding out if I had an exhibitionist streak, what lingerie and perfumes I liked and didn’t like, even drug out the details of an encounter I had with a friend that ended with me giving him head. I even admitted to her I would be open to it again provided it was the right situation and person, but I had no desire for male contact beyond that.

As time passed we both got busy and finding time to see each other was difficult. After about seven weeks of not even talking to Lisa I left a message inviting her to a party my roommate was throwing to celebrate quitting his job. I didn’t receive a reply but was happy to see her when she showed up with a few of her friends thinking I would get a little action that night. Unfortunately she had to leave kind of early but on the way out the door she told me she had been thinking about my unfulfilled fantasy a lot lately.

I wasn’t surprised when she phoned the following Thursday and asked if I was available for the next weekend. She had just finished her last exams and was looking to blow off a little steam, thinking a weekend of sex would be just what the doctor ordered. I of course agreed. She was thrilled and told me to pack for everything from going to the beach to going to a club. “See you Friday before dinner!” is how she ended the conversation before hanging up.

Friday came and a knocked on Lisa’s door just before five o’clock, she answered wearing a pair of shorts and a hoodie, not what I was expecting but looking cute nonetheless.

“Are you still interested in living out you crossdressing fantasy?” she asked bluntly.

“Sure” I said excitedly.

“O.K., this is what I have planned.” She started. ” I have been trying to plan your ultimate fantasy weekend for a while. I was thinking that instead of just one night you could spend the whole weekend as a girl. What do you think?”

“Wow” I was stunned and I’m sure it showed. “I hadn’t thought that big but it sounds like fun.”

“Great!” she shouted. “Here’s the deal, I think I know you pretty well so I want you to let me take control, you can trust me to not push you past your limits. If I do push you too far just say “I love Margaret Thatcher” and we’ll stop. Do you trust me?”

I did trust her, plus I was so turned on at the prospect my fantasy coming true I probably would have agreed to anything.

“I want you to hit the shower and give yourself a nice close shave…. Everywhere. Got it, bald from the neck down.” she said with a wicked grin. “Oh, and no rubbing out a quick one either.”

In the bathroom I found a women’s razor and a fresh can of shaving cream. After the soaping part of the shower I lathered up my right leg and thought to myself that this was the point of no return. Fifteen minutes later even my arms were hairless and I was more aroused than I could have ever imagined. I got out of the shower and toweled off on my way into the bedroom where Lisa was waiting with her wicked grin.

“While you were in the shower I took your clothes and bag back to your place for you so you have no choice but to wear what I have for you. I have also noticed that after you cum your desire for keeping with fantasies drops off so I want you to put this on.” she said handing me some sort of plastic device. “It’s called The Curve and it’s a lockable chastity device. But first we have to get rid of your hard on to put it on.” Handing me a bag of ice to cool of my privates she took the device apart. A few minutes later I was staring at my penis encased in plastic with a brass padlock at the top, trying in vein to get hard again. “The beauty of this is that you can’t even get hard let alone cum without the key which I put in my safe, so it güvenilir bahis will be a very frustrating weekend for you. Now let’s get you dressed up.”

She pulled out all the stops for me and I was soon dressed in matching bra, thong, garters and fishnet stockings with a short black skirt and a sleeveless top that showed of my mid section. She even found a fake navel ring to finish the look. After the fake breasts stuffed in my bra (C-cupish), a dark brown wig, and some make up (including bright red lipstick) I looked pretty convincing. Lisa was thrilled with her work and I was impressed.

Living in a big city has it’s advantages like being able to go out but not see anyone you know if you hit the other side of the city. “I thought we should go out for dinner to celebrate the new you!” Lisa announced. I hadn’t really thought about going out in public dressed in drag but it seemed Lisa had in fact planned on it. She could see the hesitation in my face and tried to comfort me “We’ll go to the other side of town, no one knows us. Plus you look fantastic.” Who was I to argue, I did trust her decisions.

We had a rather uneventful dinner (other than the inquisitive looks from our waitress) at a dark little Italian place where Lisa announced we were going dancing at a club next. I just about shit a brick. Dinner in a small restaurant was one thing but dancing at a club was a different story all together, I would have no choice but to interact closely with a ton of people. Lisa told me not too worry it would be dark, loud and we could pretend to be lesbians. With a smile she then reminded me how convincing I looked and that with the chastity device I wouldn’t have to worry about putting a telltale tent my skirt. The combination of wine and her confidence soon had me convinced and we were on our way. The club turned out to be quite crowded and loud so my fears were mostly just in my head, I was even the victim of a few ass grabs. The only close call was when I almost went into the guy’s bathroom out of habit but the bouncer caught me and directed me the ladies room.

We spent about two hours dancing and drinking while trying to fend off advances by several groups of guys and left around midnight at Lisa’s insistence. We caught a cab back to Lisa’s place and the whole ride there I was so horny it felt like I was vibrating.

Shortly after we got home the doorbell rang. Lisa went to answer the door and my heart was in my throat hoping whoever it was could be convinced to leave. Imagine my shock when I heard Lisa invite her friend to come in and have a seat.

“Time for your next surprise!” Lisa announced finding me in her bedroom. “My friend Dave is here and he has graciously agreed to let you give him head if you’re interested, so you might want to freshen up your lipstick.”

Dave was a rather good-looking black guy that was obviously athletic and was grinning from ear to ear. We sat down to have a few more beers and had chatted for an hour or so when my arousal got the best of me and I decided to go for it. Mid conversation I walked over to him, got on my knees and started to undo his pants. He lifted his ass to help slip them down and was greeted by his cock popping up in my face. The room was silent and they were both watching as I let the head of his cock slide past my lips and into my mouth. Like I said I had sucked cock before and I certainly knew what I liked, so I made it my goal to give him the best blowjob of his life. His moans made me think I was on the right track. Next thing I knew he tapped me on the head and told me he was cumming. I was unbelievably turned on as I held the head of his cock between my lips and he filled my mouth with jet after jet of warm cum. Normally I would have been hard as a rock but the chastity device was doing it’s job well.

Dave then stood up, zipped up his pants, chugged the rest of his beer and made his way to the door. “Thanks for the blowjob, I’ll see you girls later”

“You can drop by tomorrow if you like.” Lisa said before I had a chance to respond. Dave looked at me for conformation and all I could do was smile as he closed the door and headed off.

“My turn!” Lisa shouted as she pulled down her pants and flopped back on the couch spreading her legs and showing me her shaved pussy. “God I need to cum after watching that!”

Now eating pussy is something I have done a lot and I’d like to think I’m pretty good at, and Lisa’s pussy is a pleasure to go down on so I immediately went to work. After I brought her off we moved to the bedroom. I was beyond horny by this point and heard the best phrase I could have heard. “How would you like to fuck my brains out right now?” The look on my face said it all. “Great, I’ll just go get the little something we need then.” she said heading to the closet. To my surprise she returned handing me a strap-on türkçe bahis dildo rather than the key to the chastity device and all I could do was stand there.

“You agreed to live like a girl for the weekend didn’t you? Girls don’t have penises to use so we have to make do with the tools available. Well, go on strip down to your lingerie and strap up I need it bad.”

Like I said I was beyond horny and would have done just about anything so I stripped down and stepped into the harness pulling it up to my waist. It felt very odd to have my caged penis pushed down and out of the way while a rubber cock slightly bigger than mine stuck out in it’s normal place. By then Lisa was naked and begging for me to take her. We then screwed in about six different positions and while she had five big orgasms while I didn’t feel a thing. I started to complain but she reminded me of all the quickies we have had that she didn’t get to cum. “Girls don’t always get to have orgasms, but we can try for you next. Go wash the strap-on and give it to me.”

The final part of my fantasy was coming true next, letting Lisa have her way with me was the ultimate in submission and I was ready. It was a little weird, I had absolutely no desire for male contact in that way (I enjoy giving head but that’s it) but the thought of her taking my anal virginity was incredible. She had me remove my thong and lay on my stomach with a pillow and towel under my hips. Lisa was very gentle and with lots of lube used her fingers to relax and loosen me up. Finally she asked if I was ready and lined up the head of her dildo with my ass. With a moan from me as confirmation she slowly pushed into me. It was awkward at first but soon I relaxed and began to enjoy it, before long she was thrusting in and out like a pro. It felt fantastic. After what felt like an hour (I have no idea how long it was) she pulled out and said it was time for bed. I sat up and noticed the towel was wet with cum. I guess this was my introduction to milking. Lisa gave me a short nightshirt to wear to bed and I drifted of to a fitful sleep after not receiving any real satisfaction.

“Hey baby, how’s your ass this morning?” Lisa greeted me as I slowly walked into the kitchen.

“I’m a little sore.”

“Yeah, I imagine. I gave you quite a pounding last night,” she said with a little snicker. ” Have some breakfast and you can go shower and shave again so we can get started on our day. I’ve got a cute little bikini for you and I know of a secluded beach where we can have some privacy.”

The beach we went too was very secluded and nice. We didn’t see another soul all day, much to my relief although it was yet another incredible turn on to be in a bikini on the beach. I was really getting into this cross dressing thing. I did get some interesting tan lines out of it though.

As we were cooking dinner and discussing what club to hit for the evening Lisa told me she had invited Dave over again. “I talked to him this afternoon and he was very impressed with you skills. So impressed he mentioned he might bring a few friends over before they go out tonight.”

” How many’s a few?”

“Oh, five or six. But here’s the kicker, they would be willing to pay for your services. One blowjob apiece before they head out, and maybe one after if they strike out. Interested?”

“You want me to be a hooker, and to be my pimp?”

“Well, I did spend quite a bit of money on clothes for you and it would be nice to make some of it back.”

My perpetual hornyness was getting the best of me, it actually seemed like a good idea. I agreed.

“Great, they’ll be here in an hour and a half or so. You better go get cleaned up.”

Two hours later Dave and five friends walked through the door and sat in the living room. “We better get this started, we’re meeting people in about an hour and a half. And since we’re paying for this lets skip the chitchat. Get over here and start sucking.”

I did as instructed and got on my knees in front of him. He was waiting with his cock out of his pants this time. As I worked on his cock my hand were placed on the cocks of the guys sitting on either side of him. As soon as Dave came my head was pulled to the cock on his right. Before long I was moved to the middle of the room and surrounded by the other five sucking and jerking each one in turn. I felt unbelievably slutty and loved it. One at a time they all came in my mouth, thanked me and then they headed out the door leaving me sweaty and on my knees. It was then I realized Lisa had been recording the whole episode on video.

“Don’t worry, I’ll give the only copy to you. Now go take another shower and get cleaned up again. We can’t go out with you looking like that.”

After my shower Lisa once again had an outfit ready for me, another matching red thong bra, and garter set with güvenilir bahis siteleri black stockings topped off with red leather miniskirt and a red leather halter-top with a matching collar. With my make up applied heavily and Lisa dressed similarly we looked quite slutty as we left for the club and I was sure we would be getting a lot of attention that evening. That night we attended a fetish club (my first time) and it was one of the best nights I’ve had at any club. We were flirted with constantly all night but it wasn’t awkward at all since we were all there with little to no inhibitions and having a great time. Plus our outfits were pretty tame in comparison to a lot of the others there. The industrial trance music was great and I was having fun grinding with both the boys and girls.

Despite many offers we left alone around 3:00am and headed for home exhausted and drunk. I wasn’t really surprised to see Dave and two of his friends sitting on the couch when we came in. I actually expected more than just the three of them.

“Another round of head for the boys?” he asked.

“Sure, why not.” I replied.

“O.K., but the price just went up 10 bucks each for holding up my night of pleasure.” Lisa chimed in. They were good with the price adjustment and I was on my knees again sucking cock for the third time in 24 hours. I was getting quite adept at giving head and managed to deepthroat the smallest of the three, the other two were just too big for me. It may have been the effect of the alcohol but this time it seemed to take forever to get the guys off. This time they wanted to give me the “Porn Star Finish”, so I sat on my knees in the middle of the room with my head back and mouth open while they jerked off in my mouth and on my face. They followed that up by using their cocks to push the cum on my face into my mouth. It was something straight out of a hardcore flick. By the time they finish both jaw and cheeks were exhausted.

After the boys left Lisa and I went straight to the bedroom for more. I was soon on my knees again at the edge of the bed licking and sucking Lisa through two more intense orgasms. My poor locked up cock was aching for some attention, it was as hard as it could be and dripping pre-cum into my thong. The night played like a rerun of the previous one, me stripping to my thong, garter, bra and stockings and screwing Lisa to orgasm after orgasm in as many positions as we could think of. To show her appreciation she once again strapped on the dildo and took me in her favorite positions with me riding her until I could go no more. It was the most frustrating experience of my life. I was so turned on I was close to cumming the whole night but just couldn’t get over the edge. Needless to say my thong was soaked by the time I gave up. Luckily I was so tired I managed to sleep pretty well.

I was awakened around noon the next day by Lisa tying my wrists to her headboard an my feet to the footboard. “A couple more orgasms and I’ll give you the biggest one of your life,” she said as she crawled up and hovered her pussy just over my face. It took about fifteen minutes to give her the orgasms she wanted. She then got up and left the room returning with the key to my chastity device. Taking her time she slowly and teasingly unlocked the lock and removed the cage. My cock immediately became harder and bigger than I have ever seen it. I would have given anything to get one of my hands free to jerk off but I was at Lisa’s mercy. She took her time licking and sucking all over my shaft before finally taking me in her mouth and sucking as hard as she could. I think it took all of about 30 seconds of that before I came harder than I would have thought possible. I actually saw stars. As I opened my eyes Lisa was directly over my face opening my mouth so she could kiss me and spit my cum into my mouth from hers. I was still hard after all that so Lisa untied me and rode me until we both came again.

We ended up sleeping the afternoon away and woke up around dinnertime. I got up and had a shower to get cleaned up. It felt good to have the cage off my cock but at the same time I kind of felt naked without it. It was after getting out and drying off that I realized I had no male clothes to wear. So it was back in ligerne and skirts for one more night.

After cleaning up dinner Lisa put an open bag on the table. Inside was my outfits from the weekend, a cd, and the chastity cage with the lock in place but open.

“This stuff is all yours to do with what you please. The cd is the movie you made last night.”

“The cage has no key,” I pointed out.

“I know, the cage is yours but the key is mine. I thought you might want to be able to jerk off for the next few days, but I think your submissive side may let you put it back on again. At which time you’ll have to come see me to get out, it won’t be as quick or as easy to get out next time.”

What can I say, she knows me. That was last weekend, and here it is Friday and I’m staring at the cage thinking about putting it on and giving her a call to see what she has planned.

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