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By (user no longer on site) OP
over a year ago
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My name is Carrie and been dressing for many years now, sometimes regular and others on or off.
The desire to dress grows stronger each year.
3 years ago I had the opportunity to go to Gran Canarias; I booked up a place in Playa das Ingles.
I had heard several stories about it but most importantly that it was TV friendly.
My wife had gone to the states for a month so I was able to pick and choose clothes carefully as well as prepare myself as best I could.
It was strangely exciting packing a suitcase of mainly woman’s clothes and shoes though I still packed normal clothes in case it was not as laid back as I hoped.
On arriving at the complex I found my accommodation and emptied my suitcase.
The room looked like there was a male and female couple staying there with defiantly more woman’s products and clothes. I dressed in shorts and flip-flops and went to investigate the town and see what type of place it was.
The place seemed pretty cool and relaxed with a good selection of bars and restaurants,
I did notice there was quite a camp feel to many bars and a lot of male couples.
I decided that I wold dress in male attire that evening and see how it was. I also found the “dunes” which was a nudist beach that was pretty cool with lots of cock and tits on display.
I decided to head back to my accommodation and came across the yumbo centre; this was very busy with a really good vibe and busy bars. I decided to stop for a few drinks and a small bite to eat… I started to get chatting to a few holiday makers making small talk and asking about the place, I could not believe what I was hearing and I was starting to think Carrie would be very welcome here. I started to get a little d*unk with the beers that I decided to head back to my 1 bed apartment.
I had to dress as I was feeling so horny, I put stockings Basque on and a lovely pair of blue high heels. I then gave myself an enema and lubed myself up and slowly slid a butt plug in me.
I finished off wanking myself and licked the cum off my fingers. I then settled down on my bed and drifted off to sleep.
I must have waked up around 11pm as I could hear loud music coming from the bars. My butt plug was still in me and I could feel it sitting there nice and snug. I got up and went to the balcony and after looking around I ventured out still in my Basque stockings and heels. I was overlooking the pool and I could see guys kissing, couples kissing all quite openly and not a care in the world. That was then decided that Carrie was going out.
I removed my Butt plug and gave myself another enema and relubed myself..
Next I had to decide what I was going to wear, I chose something that was more evening wear not to tary and slighy classy. It was a gold sequinned dress which was mid-thigh so I could wear stockings that would not be too noticeable, I was more interested in passing rather than making a statement. No matter how many times I go out I will always get nervous and this was no exception. I applied my makeup and finished my lips off in a ruby lipstick and touched it up with a gloss.
I gathered an purse money and hotel card and then I was ready to go.
I nervously entered the hall way and made my way to the lift, I pressed to go down and waited for the lift to arrive.
When it come there was a couple in there I froze then stepped in and smiled as best I could and just looked down.
The lift arrived at the lobby and I walked out as quickly as possible, my heels wear making a clicking as I walked and just seemed incredibly loud on the tiled floor. I just wanted to disappear and my legs where shaking.
I got to the front doors and a man opened the door for me and said good evening I thanked him and went through into the night.
I felt a little better and there was people walking and laughing all around me but no one paid any particular interest to me. This made me feel a whole lot better and more accepted.
I walked into the yumbo centre where there were lots of bars and found one with a few empty tables, I took a seat and waited. The waiter came to the table and I was asked if Madame would like a drink, I chose a white wine and ice. After a couple of minutes he came by and delivered a bottle, I said I only asked for a glass and he just said a guy at the bar ordered it and was on him.
I asked which guy and he pointed out a large black guy who was very fit and had a lovely smile, I smiled back and mouthed thank you to him. The man came over and introduced himself as Colin and asked if he could join me, I was not prepared for this and said sure as feminine as I could. He was very relaxing and told me I look incredible and then he asked how long have I been dressing, this was a shock as he obviously saw through me but he said I looked extremely passable but was unusual to see tall girls and had to double take and look a little closer. He liked what he saw. We started talking and laughing together as we shared the bottle of wine, he then ordered another bottle and moved his chair closer to mine and put his hand on my knee.
He then leant in to kiss me; it was lovely, tender and soft. A little giddy with alcohol, nerves and excitement I responded immediately running his hand over my thigh and feeling my suspender straps. I started to rub his thighs as well and brushing over his loin area he was getting aroused and god did he feel big.
We stopped kissing and talked some more with him stroking my thighs gently and whispering in my ear. Could not believe this was happening on my first night in a foreign country. We finished the wine and then he said he wanted to dance, I said ok and we went to a club /bar with was loud and packed he led me to the dance floor and held me as we dance he turned me round so my back was facing him and told me to start grinding to the music, I felt so alive I stared rubbing my bum again his groin and could feel his hardness through his trousers. I was so turned on that he was turned on I knew then I was going to sleep with him, we kissed some more and touched each other up in the club that I said I wanted to go home, he agreed and we left the club and walked hand in hand to the hotel. We went to the lift and stared kissing some more in the lift and we fell out of there. I led him to my hotel room and struggled to get in as I was so excited and nervous.
We just headed for the bedroom and he pushed me on the bed and stared to take his top off, his body was gorgeous, hard and toned and a chest to die for he then started to unbutton his trousers and his cock was unleashed.
It was big and thick and very hard, I just sat straight up and went for it with my mouth, his pre cum was delicious, all of a sudden he just came in bucket loads and what seemed for ever , he filled my mouth and I swallowed most of it , I couldn’t believe what was happening, I was sucking a huge black cock on my 1st night and he just came in my mouth… I was disappointed because I hoped he would fuck me before he came. He apologised and said it was most incredible bj he had. I got up and he kissed me some more and then suggested he pour us a drink on the terrace. I said ok and went to the terrace he came up behind me and started kissing my neck he was turning me on he then reached for my bottom and started playing with it and then he slowly started fingering me, he was amazing had an amazing touch, he stared whispering in my ear how the night wasn’t finished and I was going to be his bitch and how he was going to make it a night to remember. I was so glad I had lubed up and he was finger fucking me now and I started to feel weak, he then got my hand and started to put it on his cock and I could feel it growing. I could feel it getting harder and harder he then hoisted my dress up and pulled my thong to one side and guided his cock into the base of my bum and slowly pushed, god was he big and forceful I felt him enter me and I was starting to whimper, here he was thrusting hard into me on the balcony and I was looking over the pool trying to be a quiet as I could so not to draw attention to myself. I felt myself rise on tip toes in my heels and rocking back and forth as he thrust into me, the feeling was intense. I asked him to stop and take me to the bedroom he pulled out slowly and led me to the bedroom and he laid me on the bed, he kissed me some more then turned me over and started to kiss my bum slowly working to my open and lubed up hole when he started to rim me. He pushed his tongue in as far as he could get it and ate me, it was like electric pulses where tingling through my body.
He then got to work with his fingers again and then turned me back over so I was on my back. Placing a pillow under me he raised my legs so they were on my shoulders and put the tip of his cock against t the entrance of my hole. Again he pushed into me and each cm felt like heaven thrusting hard and steady and kissing me as we made love. I truly felt like a woman and wanted to please him in every way, after about 10 minutes of pleasurable fucking I asked d him to pull out and went to suck his cock tasting me on him was amazing, I then asked him to lie on the bed and spread my legs and then straddled him. I rode him for all my worth and kissed his magnificent lips and chest my cock was getting hard and he stared to wank me as I bounced up and down on his hard cock, it was then he cum for the 2nd time that evening it hit me like an inferno and with that I cum as well all over his black skin, it was a beautiful site and I couldn’t resist kissing him and then easing myself off his cock I licked up my cum I spent on to him as well as cleaning and licking his cum off his cock as well as my own juice. We kissed some more and then fell asleep together holding each other tight.
It was a wonderful morning when we woke up.
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