Kaley said that as the acting manager of the hotel she was sure she could find me a room if I wanted to stay another night. I invited her up to my room but she said she would have to go home to get a clean (and dry) change of clothes for the following day but I was welcome to go with her. I said I would run up to my room and get changed but she said if she had to go home wet I would have to aswell. So we grabbed the rest of our clothes, rinsed them in the shower, rung them out as best we could and headed off. Kaley put our wet things in the drier and we went to bed and made love before drifting off to sleep. 

The next morning I was woken by Kaley's alarm clock and despite me trying to stop her she insisted she had to get up and get ready for work, but she told me to find her a nice "swimsuit" to wear to work while she was in the shower. I rummaged through her drawers and cupboards and finally found an outfit I would like to see wet but which was professional enough for her to wear to work. This consisted of a sky-blue dress, which was about knee-length and had 3/4 length sleeves, which I had matched with a pair of white leather pumps and stockings, for underwear I went for a white cotton leotard which had a boy-leg style bottom, short cap sleeves and a neckline which plunged down towards her cleavage. Kaley came back from the shower and I watched her get dressed, she seemed surprised at my choice of underwear and said that she had lots of sexier stuff, to which I replied they might be sexier dry, but when it was all wet and see-through what I had chosen would be pretty hot. 

There was a local golf course I had been planning to try before I drove back, but since I was staying I decided to take a cab so I could have a few drinks. It was a good job I did because we had a dozen beers on the course before even making it to the clubhouse. By the time I got back to the hotel it was past six and I was feeling slightly drunk. I saw Kaley at reception and she said she would get some room-service sent to her office if I fancied dinner, I said it sounded like a great idea and that I would run up to my room and stash my gear. Knowing we were going to end up in the pool I left my phone and wallet so they wouldn't get wet, I also decided to remove my boxers and go "commando" since I knew my lightweight silvery pants would cling tightly to me when they got wet. I was also wearing a white cotton polo shirt, socks and sport shoes. 

We head a nice dinner and were chatting away when Kaley looked at the clock and saw that it was 9.15, she said she would close up reception early as she felt like it was time to swim. We went into the pool room and as we shared a kiss standing next to the pool, I felt Kaley push me and I fell backwards into the water. Normally I would have grabbed her and pulled her in with me, but I was hoping to watch her climb into the pool more slowly. She then told me she wasn't allowed to close reception early and would have to go back to the desk for 10 minutes, I asked her why she didn't say that to start with and she said she remembered me saying how I liked to be teased and forcing me to wait to get her wet would be a massive tease. 

I couldn't argue with her logic so as she left I had a swim, enjoying the feeling of my wet clothes floating around me. After a few minutes of swimming I climbed out of the pool and sure enough my clothes were plastered against my body and I was pleased I had forgone underwear as the silky smooth material against my groin felt amazing. I headed to the changing room and looking at myself in the mirror, I thought I looked pretty good with my shirt see-through and everything clinging to my skin. I took a condom from the machine and put it in my chest pocket knowing it would be clearly visible through the wet material. I was walking back to the pool when I remembered what Kaley had said the night before, so I unzipped myself and let my cock hang out of my fly. 

I jumped back into the pool and the feeling of my cock floating uncovered while my balls, legs, and butt were being caressed by the wet silky material was starting to give me a semi. Suddenly I heard the door open so I bolted out of the pool and struck a body-builder-like pose, with water streaming off my body and my semi-hard cock poking out of my pants. To my surprise it wasn't Kaley who walked round the corner but a blonde woman wearing a hotel bath-robe. She was staring at me with her mouth wide open in shock, and I don't think either of us were able to speak. I was trying to get myself tucked back in when I heard Kaley running through the door yelling, "don't go in there, the pool is closed". 

The blonde woman, who I later found out was named Susan, asked what was going on, and Kaley said that since the pool was supposed to be closed we were going for a private swim. Susan asked why I was fully clothed and Kaley explained that we thought the look and feel of wet clothing was sexy. Susan looked me up and down and said she could see it looked sexy but she couldn't imagine that it would feel good, to which Kaley replied that she thought the same way until she tried it for the first time the night before. She still didn't look convinced, and then Kaley asked her if she wanted to try it, Susan said she would give it a go but she didn't have any clothes with her. Kaley smiled at me, undid the zip and as she started to lift her dress over head she told Susan that she could try her dress. 

As Susan removed her robe I saw she was wearing a red one-piece swimsuit underneath, and despite being an older lady (I would guess 45-50), she still looked good. She put on Kaley's dress, and Kaley told her the best part was the shoes and stockings and proceeded to remove them and hand them to Susan. As she finished getting dressed Susan said to Kaley that she had seen wet t-shirt contests before and that her underwear would go pretty see-through. Kaley replied that that was the point but that she wanted to tease me for a little bit longer so she picked up Susan's robe and put it on. 

Kaley lead Susan over to the pool steps and climbed into the pool, wetting the bottom of the robe. Susan dipped her foot in the water and lifted it back out saying it felt weird, I could see the wet part of her stockings were completely see-through apart from the seam up the back. She stepped back into the water then dipped her other foot in and with Kaley leading her stepped down into deeper water. I figured the girls would tell me when they wanted me to be involved and sat down on a nearby chair. 

As Susan stepped further into the pool I could see the water engulf the bottom of her dress and turn it a darker blue. The girls continued to wade into the water until it was over their waists, where they stopped and faced each other, I could see they were both running their hands over the wet part of Susan's dress. Kaley began filling her hands with water and pouring some onto Susan's breasts, the she dipped backwards, sinking down til her shoulders were underwater. Susan followed and the two girls started swimming around the pool. Susan was looking less and less uncomfortable and after a few minutes said that at first she felt weird but it was starting to feel more and more sexy. 

I was enjoying watching them floating on the surface on their fronts and backs and swimming underwater, but decided I had had enough watching and was about to get up to join them. However before I could get up Susan whispered something to Kaley and they swam to the steps, Kaley climbed out and the robe she was wearing looked like it must have been holding about 100 liters of water, but as Susan climbed out of the pool she captured my attention. The dress had become a really dark (almost black) navy and was clinging so tightly I could easily make out the shape of her swimsuit underneath, and even the tops of her stockings. 

The girls started walking towards the dressing room and Kaley turned to me and whispered "stay here". I waited for what seemed like ages and was starting to wonder what was happening when Kaley emerged from the dressing room. She had changed into the dress and had obviously re-wet in the shower as the water was still streaming from her, and it looked as if it was painted on. She beckoned me to come to her and as I approached Susan appeared from the changing room door. She had changed into the leotard and was still wearing the stockings and heels, and had also obviously re-wet her clothes as they were completely see through and I clearly see the birthmark on her breast and the shape of her pubic hair. 

Susan said "I wanted to know if this looks sexy", and started doing a pirouette. I had temporarily forgotten the English language but somehow managed to stammer out "yes". I had reached the girls and we were standing face to face when Susan said "and do my stockings feel sexy", I couldn't believe this was happening to me as I reached down and ran my hands up and down her legs feeling the wet material, replying that they did, and then she amazed me by saying "and does my leotard feel sexy?" Since my hands were on the backs of her legs I ran them up her wet stockings, over the lace trim and onto the naked skin of her legs, reaching more wet material I paused at her butt, then continued up her back, over her shoulders and paused at her breasts, cupping them in my hands and playing with the nipples, then continued my exploration across her stomach and down between her legs, where her pussy felt like it was getting wet in another way. 

It must have been obvious that I was speechless as she said if I couldn't tell her how sexy it looked, I would have to show her, and she reached down and unzipped my pants, and my hardening cock sprung free from its prison. I was still trying to figure out what was going on when I felt Susan reach into my top pocket and pull out the condom I had placed there earlier. She said that she couldn't cheat on her husband but hoped that she could watch us use it. 

Kaley took the condom from her and lead me into the pool, we were standing in waist deep water and kissing and I could feel Kaley sliding the rubber onto my cock. I lead her to the shallow end which was about mid-thigh deep, bent her over the side of the pool, lifted her dress and entered her. After I had cum I looked around and couldn't see Susan anywhere, after spending a couple of minutes recuperating Kaley suggested we go and look for her. On entering the changing room we heard the shower running and turning the corner we saw Susan sitting on the floor masturbating. We arrived just in time to see her cum, and the sight caused me to start getting hard again. 

Kaley saw this and knelt infront of me and started sucking me off right infront of Susan. Just as I was about to cum Susan held out her swimsuit and I shot my load into it, she then immediately put it on and I know my sperm was getting squished between her stomach and the wet material. She said that that way I could be next to her as she slept, and with that she left. Kaley laughed and said that wasn't how she expected the night to turn out, I agreed and asked her if she was ready for bed. She put on her underwear, stockings and heels and we headed up to my room, where we went straight to the shower to make sure our clothes were good and wet, and then climbed into bed still in our wet clothes and shoes, where we made love and drifted off to sleep. 

The next morning we ordered room service for breakfast and finally it was time for me to leave. Kaley had brought a change of clothes and we went down to reception. The man behind the desk looked surprised to see Kaley as she wasn't supposed to be working and she said she had come in to do some paperwork and that she could check me out, unsurprisingly I didn't have to pay for the extra night. We exchanged phone numbers and Kaley told me to call her if I fancied a dirty weekend away sometime.

A while ago I was sent on a business trip, I left on the Tuesday afternoon and by the time I had driven four hours to reach my hotel I was exhausted. I checked in and was served by a cute young redhead who according to her name badge was named Kaley and was the acting manager. I guessed that she was about the same age as me and while we chatting there was some pretty serious flirting going on. 

Once I was all checked in, I went for a walk and a bit of an explore around the hotel. I found the indoor pool and noticed that there were no windows overlooking the pool area, I thought to myself that it would be an ideal place to swim fully clothed. I was contemplating the odds of someone walking in while I was swimming fully clothed and thinking I was weird, when I heard the door open and two older women walked in, they asked me if I was swimming but I said I was just having a look around and would leave them to it. On the way out I saw the sign that said the pool closed at 9.30. 

I knew I had to try the pool at some point during my stay and that night I headed to the pool around 10, thinking that if I was outside the opening hours I wouldn't be disturbed but unfortunately the door was locked. I thought about going swimming a few times but the memory of the two women had me scared that someone would disturb me, and I never had the guts to go for it. 

During the week I had got to chat to Kaley a few more times and we continued flirting and it felt like we had a real connection. As I was going out on Friday morning I saw Kaley sitting behind the reception counter wearing a black suit jacket with the collar of a white blouse visible underneath. When I returned after work she had removed her jacket and I could see that she was wearing the blouse underneath a black strapless dress, that contained a corset stopping just below her shoulders. I decided this could be my last chance and asked her for a favour, when she asked what I wanted, I asked if she could leave the pool door unlocked so I could have a private swim when I got back from dinner. Kaley said she finished work at 9.30 and went for a swim afterwards and that I was welcome to join her if I wanted to, I confessed that the reason I wanted a private swim was because I didn't have a swimsuit with me, and she just gave me a flirtatious smile and said neither did she. This wasn't quite what I had planned but I had never have a girl come onto me like this before and I wasn't going to turn down the opportunity. 

I was meeting an important client for dinner, but decided I needed to make my excuses and left early, heading back to the hotel just before 9.30. Kaley was sitting behind the reception desk and we started chatting, she looked at her watch and noted that it was after 9.30, so she closed up the reception area and put up a sign saying it would re-open in the morning. We walked over to the pool area and as Kaley was locking the door behind us so we wouldn't be disturbed, I pulled my phone and wallet out of my pocket and left them on a nearby table. 

Kaley walked towards me and started removing her jacket. I told her not to take her jacket off and she looked at me with a confused look on her face. She said she thought she had been clear that we would be skinny-dipping and was confused as to why I didn't want her to take her clothes off, I told her that when I said I didn't have a swimsuit I wasn't planning to skinny-dip. She said I had better explain what I was meaning as she was completely lost, and I said it would be easier to show her. I walked over, picked her up and walked towards the pool. I stepped into the pool and felt the water flooding into my shoes, she looked at me and asked what the hell I was doing. I just smiled and stepped further down into the pool, soaking my black slacks to about mid-thigh. She screamed and exclaimed that I had got her shoes wet, I looked down and sure enough her black leather pumps and stocking clad feet were underwater. 

She suddenly realised what I was planning and started telling me that I wouldn't dare get her all wet and to put her down. I asked if she was sure that she wanted me to put her down, she said yes then realised where she was and changed her mind, but I told her it was too late and stood her up in the pool infront of me. As she is a bit shorter than me and in slightly deeper water the water was over her waist, and as I looked down I saw her skirt floating up around her waist and the bottom of her jacket was also underwater. She started screaming that she couldn't believe I did that, and was splashing water against me, wetting the front of my black sports coat and light blue silk shirt. 

I thought that she was actually pissed off with me, and that I had ruined the evening but as I looked up I saw the flirtatious smile on her face, and decided that she wasn't really that pissed. I also took the smile as a sign and leaned in to kiss her. As our lips locked and our tongues intertwined I started walking forwards, leading us into deeper water. Kaley tripped and fell backwards, and we both plunged underwater. When we finally broke our kiss we were still underwater and my lungs were burning from lack of oxgen. When I surfaced I saw Kaley looked how I felt and we both swam over to the pool steps and sat on the top step, where the water was just over our waists. 

Kaley slipped her jacket off and put it on the edge of the pool, I could see the shoulders of her white blouse had gone completely see-through revealing black bra-straps below. I decided to follow her lead and removed my jacket depositing it on top of hers. Kaley asked me what the hell I was doing getting us both in the pool fully clothed, so I told her how I found wet clothing extremely sexy. She had that confused look on her face again so I proceeded to explain how when wet clothes cling to the body and become see-through or shiny, they reveal everything beneath while maintaining the modesty of being fully clothed, which I find to be the ultimate tease. Kaley told me she understood what I meant and that she was finding the feeling of her clothing very sexual, especially the feeling of her wet stockings. 

I felt like that was an invitation and began running my hand up and down her legs feeling the wet material. We then kissed and our hands started roaming over each others bodies, I found the buttons on the front of her corset and started undoing them and soon my hand could slip beneath her corset and rub her breasts through the two layers of wet silky material, feeling her erect nipples straining against their wet confines. Looking down I could see her bra through her wet blouse and saw the black material was covered in red and silver embroidered flowers. 

I lifted her skirt and saw she had matching panties, and I began to rub her snatch through the wet material, ducking underwater I pulled her panties aside and buried my mouth in her wet snatch. She wrapped her legs around me and I could feel her stockings brushing against my head and the heels of her shoes digging into my back. She grabbed hold of my hair forcing my face deeper into her crotch and for the second time that day I felt like I could almost drown, but luckily I heard her moan, felt her body convulse and as she came she released me and I could lift my head above water and get some breath. 

I sat back on the step next to her and we both needed a minute to recover, then she told me it was one of her best orgasms and she felt it was only fair to return the favour. She unzipped my fly, freed my cock from my boxers and ducking underwater expertly took it in her mouth. It didn't take long before I cam and filled her mouth with my warm seed, she looked at me with that same cheeky look on her face and proceeded to swallow it all. She then told me there was a condom machine in the mens bathroom if I needed one. 

I climbed out of the pool, my now flacid cock still hanging out of my fly. I found the machine and turned to head back to the pool and saw Kaley standing infront of me. Water was streaming of her hair and body and she had removed her dress and bra and through the wet white shirt I could clearly see her wet breasts. 
She said she liked the look of my cock hanging out of my pants as she took the condom from me and proceeded to thread it onto my hardening shaft. I took her by the hand and led her into the shower, where I turned her round, leant her against the wall, pulled down her panties and had my way with her as the water from the shower pounded against the wet silk stretched across her back. 

When she felt me release my load, she stood, turned and wrapped her arms around me, we kissed and then she said it was a shame that I was checking out tomorrow as we wouldn't be able to do this again. I just smiled and said that aslong as the hotel had a free room I could always stay one more night......

the family rule growing up was that if you couldn’t be bothered changing into swimwear to use the pool you could strip off and dive in in your underwear

about the time i became sexually interested in women my sis decided to stop wearing underwear in the pool and start wearing a swimsuit which was really annoying, especially since she hardly ever wore a bra and opted instead for a white singlet, which i knew would be like having a private wet t-shirt contest

i meanwhile only wore white cotton undies, which i kept swimming in, and which would go completely see through when wet

when we were both 16, mom and dad went out of town for the night and left us at home alone

i was taking a bath when i heard my sis come through the front door, she called out my name and i yelled back that i was in the bath, she said that she needed to talk to me

i heard the door open and she asked if i was decent, i replied of course not, i was in the bath, naked, but if she needed to come in she could throw me some undies, and it would be just like we were in the pool

some undies came flying through the door and landed in the bath and i slipped them on, telling her i was decent, she came in the room

so she sat down on the edge of the tub and started talking to me about something (can't remember what it was now) and after a few minutes her hand lowered down into the water

i don't think she even noticed what she was doing but she was running her hand back and forward through the water and every so often she would rub her fingertips against my cock

i was starting to get turned on and was "pitching a tent" in my wet white briefs, my cock was standing up so far the head was now out of the water and only covered by the wet see through material of my boxers

after another couple of minutes she looked down and saw my hardness and made some comment, i told her it was her fault as she was rubbing against my cock but she claimed it was an accident

then she looked back at it and remarked that it was a lot bigger then her boyfriends, and started poking it with her finger

i didn't really know what was going on so i grabbed her and pulled her in the tub still wearing all her clothes, black knee length boots, jean skirt, and blue and yellow checked cotton shirt

we started having a tickle/wrestling fight like we did as young children and were rolling around in the bathtub, it didnt take long for all of her clothes to get completely soaked

after a few minutes i was on top and i reached down and ripped open her shirt, and thankfully she had worn a singlet underneath, and it had gone completely seethrough

i started rubbing her tits through the wet material and when she didn’t object i pulled down her top and started motorboating my twin sister

she still didnt object and now i was running my hand up and down her legs aswell, i kept rubbing higher, until i was under her skirt and feeling the wet material of her panties

before i know it my head was under her skirt and i was kissing/licking her pussy through her wet panties, i slipped her panties aside and started fingering/licking her

as i had only been with one girl i was pretty incompetent but she seemed to enjoy herself and was grabbing hold of my hair and moaning

after a few minutes she must have cum as she relaxed and let go of my hair, then she told me to stand up

she knelt in front of me and started stroking my cock through my wet undies, then she pulled them down and took my cock in her mouth

i didnt last long before i blew a massive load all over her face and hair, i leant back against the wall to recover and she started to wipe my cum from her face, lick her fingers and swallow my juice

she got to my cum that was in her hair, but i told her to leave it there

we climbed out of the bath, stripped off and dried off then i went to my bedroom, put on some pajamas and went downstairs

my sis arrived a couple of minutes later also  in pajamas but with my cum in her hair, we were both a bit shocked i think and sat down and watched a movie and didn't mention what had happened

that was until the next morning when over breakfast she brought it up

i told her how sexy she had looked in her soaking wet clothes and how i thought her pajamas would look sexy wet aswell

so i picked her up in her pink silk pajamas, carried her out to the pool and jumped in

i told her to climb out so i could see how she looked, the material had turned pretty seethrough and was painted to her tits and stomach, it was also clinging to her pussy and revealing a large cameltoe

i asked her if she wanted to go a step further then the night before, and she said she would but she wanted to do it right

she appeared a few minutes later dressed as a french maid (i later found out that she had found the costume in my moms wardrobe)

she dived into the pool and we kissed then i carried her over to the shallows (water was just above her stocking tops) and leant her against the pool wall

lifting her skirt i found she was wearing crotchless panties, so i pulled down my pajama pants and slid in

we spent the rest of the day in and around the pool, every couple of hours she would go into the house and come out in a different outfit, and everyone of them ended up being ripped off and floating around in the pool

that evening we worked out we needed to wash and dry a few loads of laundry and when my parents returned the following day they were none the wiser