I have this group of Friends that I’ve known since the 80’s stemmed from meeting my buddy Phil at work and later meeting his siblings. This story begins in the mid 90’s and extends to the mid 2000’s and involves 2 of Phil’s sisters, his girlfriend’s sister, another friend and friends of theirs. The girls names for reference are Phil’s sisters Shawn who I would eventually date for 2 years and Char. Phil’s girlfriend’s sister Deana. Deana is 10 years younger than me. Shawn is 1 year older and Char 3 years older. Our friend Debbie who is about 3 years younger than me. Their friends Natalie which I don’t know her age and Nicole 3 years younger than me. Occasionally there was a couple other girls whose names escape me.

It all started when my other buddy Pat, Phil’s brother got divorced and moved Phil in to help with costs. Then decided to make life really cheap by bringing another roommate in who didn’t work out which is where I came in. Then Phil’s girlfriend moved in. Things were really cheap and we went in on a hot tub and a 1978 Corvette Stingray. We became party central and spent the summer in the pool by day and hot tub by night. Pat was a cop so some of the people over were fellow officers and boy did they party. One day one of them got the idea to take his swimming trunks off in the pool and throw them on the deck which Char grabbed and took off running with them. He then got out and grabbed the solar cover and wrapped it around himself and chased her down the street with everyone laughing. So our friend Scott did the same thing without anyone grabbing his shorts. I noticed nobody was offended and generally thought it was funny and I was almost tempted to do it myself but I refrained.

A week or so later I was in the pool and Debbie, Nicole, Shawn and Char were on the deck in their bikinis sunbathing and Deana was in the house cleaning. The conversation around the pool was about the guys skinny dipping the week before and how they liked the guys swimming naked and not being pressured to skinny dip themselves but why would they. 2 brothers one being a cop and a girlfriend of one of the brothers who was going to pressure them. They commented that although I was in the pool that I hadn’t skinny dipped that day and joked about me maybe having a small wiener. Well that did it I took off my swim trunks and threw them on Debbie who wasn’t the prettiest girl there that day but who absolutely had the best body on her lap and as I was getting out of the pool the girls were laughing and screaming Debbie got up and opened the bathroom window and threw my trunks in and closed the window and I danced in front of them for like 10 seconds and headed to the bathroom window to climb in and retrieve my swimsuit when I saw Deana in the window staring and laughing. I climbed in and she went for my swimsuit and I caught her right away and immediately grabbed my suit away from her my cock pressed against her back. She and I soon were in our swimwear and joined the other girls on the deck. I was hard most of the rest of the day.

Next was Christmas time. We had a party at the house and at one point all the guys except me and a few girls decided to go to the bar and have a couple of cocktails and invite a few bar friends over. The girls remaining were all the above named girls and Phil’s girlfriend. The sister bought me some men’s bikini underwear zebra striped and leopard print and brought it up so I got them and showed them and all the girls were like woohoo and I joked about modeling them and they all egged me on so I did. I went to the bathroom and put the first pair on and got myself semi hard and walked out to a lot of cheers and spun around so they could see it all then they wanted to see the other pair so I stripped them off right there in front of them and slipped the other pair on. They went silent for a second or 2 then roared with cheers and laughter and then I stripped off that pair which I received a couple ass slaps and went to the bathroom and got dressed again.

My buddy was killed in the line of duty and the shenanigans stopped for a long time and then I got injured and the pool and hot tub were in disrepair. 6 months of events to fundraise for his kids and to memorialize him had ended. The last one I hadn’t attended because I was already drunk and passed out on the couch. Phil and Shawn, Char, Nicole, Natalie and Deana came home. At first Shawn came in and saw me passed out wearing the same clothes I had wore for several days. Back then I only owned one pair of shorts and a bathing suit and alternated between them when I was washing clothes and pants were hard to get on with my knee injury and brace. She assumed I they were dirty and grabbed a pair of her deceased brothers shorts and took mine off and was replacing them with her brothers shorts. I should say Shawn, Char and Natalie were married at the time. Their husbands were aware of the male nudity that had occurred but either thought it was funny or trusted their wives. I mean hey the guys went to strip clubs right. But anyhow while Shawn was pulling the shorts up my legs the other girls came in and were like what are you doing. An idea occurred in Deana’s head and it was a bad one. She grabbed the shorts and pulled them off and there I was in and out of consciousness with a terrible heading lying there only in my underwear with 5 women staring at me wondering what Deana was up to. Deana comes out with this really short lacy pink with purple polka dots party dress. She then pulls off my underwear and grabs the dress and starts pulling it up my legs and I was in no condition to fight but I fought the best I could. So she straddles me facing my feet and sitting on my cock and I’m kicking my uninjured leg which Char grabs and holds down making it easier for Deana to pull the dress up my body and she gets off me and I have a boner and I’m a bit more alert and with her off me I can struggle easier… lol. If you girls want me naked then I will not struggle but a party dress I’m fighting with all I got which wasn’t much. Then Shawn grabbed my arms and Deana got the bottom of the dress where it was supposed to and she couldn’t get the straps around my shoulders because I’m nearly 6’6” but she was trying until Phil walked in and was pissed because I was drunk and injured and was clearly not capable of defending myself and the injury was enough I could be heard crying at night when the pain killers wore off. Shawn was spending the night on the love seat and once everyone was gone she got the dress off me and put on my original shorts which were men’s red wings sweat short shorts without the underwear and seeing I had a boner she later slipped her foot into the shorts and rubbed my cock.

A couple years after that we were at Shawn’s house. Everyone was outside I took a break from it and sat at the Kitchen table. Shawn walked in and asked if I was okay and I said yes I just needed a break and that I just broke up with someone who she knew that I wasn’t really hurt by breaking up with her but that I really missed hanging out with my female friends like her and the others without my ex being present which was in Shawn’s eyes was me saying I loved her as a friend so she stood me up and hugged me. Shawn was wearing a short mid thigh sundress. As we pulled away from the hug she grabbed the top of the sundress and pulled it outwards where I could see she wasn’t wearing anything underneath and I leaned in for a closer look and it was wonderful. At this point she’s seen me naked several times and now after these few years I’ve seen her naked looking down and we were more even now.

A couple years after that Shawn was divorced and had a new guy but they were having problems so she went to stay with sister Char and Chars husband for a while. I came over to pick Shawn up for a show which ended early. Chars husband was at work and she invited me in for a few drinks once I had brought Shawn back home. At first we were playing cards but that got boring really quick and everyone was making suggestions for things to do and I joking said truth or dare which they thought would be fun. After some more mild things Shawn dared me to strip which they both had seen me naked so I did very quickly and then they dared each other to do thinks to me. Stroke my cock, cup my balls, kiss my lips, smack my ass, rub my legs and for me to bounce my cock . The most daring was the last thing was that Shawn dared Char to take a shower with me. That was awesome actually I’m now seeing Char who is completely naked and her sister is in the bathroom watching us shower. About 2 months later Shawn and I were seeing each other as boyfriend and girlfriend for about 2 years.

Last but not least about 5 year after Shawn and I were broke up a group of us went on a bus trip to a casino. Shawn Char and I roomed together, I in one bed and them in the other. One day I joked about don’t be surprised if I come out of the bathroom naked and they responded go for it so I did. They sat side beside on their bed and stood me in front of them and looked me over. Shawn offering me to her sister who declined because she was still married though unhappily at this point. She would stay in the marriage another 15 years both her and him unhappily but she said she would not mind me staying naked for a while. They called their eldest sister Mary who had never seen me naked and told her they had a naked guy in their room and to come over. She didn’t believe until I opened the door and shock and awe was the best description I could give the look on her face. She stayed about 30 minutes and left. We went to bed and I laid naked on top of the bed until it was time to dress and leave. I felt a hand on my thigh at night and don’t know which one it was but I hoped it was Char considering I had already been with Shawn in every way.

I’m still friends with Shawn, I haven’t seen Char in about 3 years, haven’t seen Mary in about 4, Deana and Debbie are FB friends, Nicole I still speak with from time to time. Natalie is now divorced and I haven’t seen for 25 plus years but I speak to her ex husband from time to time and see at different shows and museums. I speak to Phil and his now wife fairly often.