A day by the pool with my boss and her sister
About 20 years ago I became friends and developed an unspoken crush with a young woman I'll call Chris (not her real name). She was about 5'5" and curvy with brown hair, beautiful green eyes, and medium sized breasts. She was smart and had a great sense of humor. What was not to like? Probably my favorite thing though was the fact that her nipples liked to harden on a fairly frequent basis and were very much on display no matter what type of top or bra she was wearing. I hope that doesn't make me appear to be drifting toward the "shallow end" of the respecting women pool.
Anyway, shortly after getting to know her, a job opening became available where I worked and I knew she could get the job, and she did. After what seemed like an awfully quick 10 years of working together Chris had married, had a couple of kids, and had become my boss. I was ok with that (alright, it bothered me a little bit, but was happy for her). I was comfortable doing what I was doing and didn't need a promotion. My annual pay raise with increased vacation time was good enough for me.
My reason for writing this is because Chris called me one warm summer day and said that her husband and the kids were away visiting his parents. She needed to stay home to take care of a few things and she thought it would be a great idea if her sister Gina and I would come out to her house to hang out by the pool and have a couple of cocktails. Her house is in what I would call the semi-country. There were a lot of houses, just not right next to each other.
When I got there, Gina had already arrived. Both of them greeted me at the door with a drink in their hands. Gina took me out to the back deck while Chris made me a raspberry vodka and tea. The back deck was large, covered with a retractable awning and above ground. You could just walk right up to the edge of the above ground pool and jump right in from the deck. She also had an 8 foot high fence that offered complete privacy.
After about an hour of small talk and joking around, Chris suggested that since it was getting so hot out we should go for a swim. I told her I wished she would have told me on the phone so I could have brought my suit. I had a nice pair of shorts on that I didn't want to jump in the pool with on. One part that I didn't mention to Chris was that even though I'm a pretty good looking guy, I have a small penis that is clean shaven and I'm not exactly comfortable just putting it on display for my friends. I guess there's a little insecurity thing going on there. Chris then said that I DID bring a suit......my birthday suit. There was no smiling or snickering from either Chris or Gina. They both seemed matter of fact about the possibility of seeing me naked. I on the other hand was not and said I didn't think I could do that. Chris then said "We're all adults here and it's not like Gina and I haven't seen a penis before. We're both married, had boyfriends, and have boys. It's really no big deal."
After a little more coaxing, I agreed. So while they went inside to change, I took off my clothes and jumped in the pool before they could see me. I was actually enjoying the warm water as Chris and Gina appeared in their one piece bathing suits and jumped in. Gina asked "Are you ok now?" And I said "I'm getting there." It didn't take long before the thought crept into my head that I was now naked not only with two women, but one that I've continued to have a crush on just a few feet away. And that is when I felt myself start to harden. It took about 30 seconds to go from flaccid to it can't get any harder. I was so thankful I was in the water so that I could bide my time until it went away.
That only lasted for a few brief moments however, when Chris asked me if I'd be a dear and go get our drinks, top them off, and put them down on the edge of the deck next to the pool. I said "Right now?" And she asked me "why not?" I didn't want to tell them why, so I tried to convince myself that it's no big deal for them to see me while desperately hoping my erection would go away by the time I had to turn around on the deck to bring the drinks. They were both facing the deck while continuing their conversation with each other as I ascended the ladder. They never stopped talking while I refilled our drinks. Now I had to turn around and face them still completely hard. I wish I could have ran and jumped back in the pool, but I had to walk slowly so I wouldn't spill the drinks.
As I faced them, they were both looking at my face and then almost simultaneously lowered their gaze to my hard hairless little guy. They continued to talk as they watched me bring the drinks and thanked me as I re-entered the pool. Maybe another half an hour passed, enough time for me to soften and get hard again a couple more times, when it was time to get out of the pool.
The girls got out first and grabbed towels to dry off a little bit. I followed sporting my third erection of the day and was reaching for a towel as the girls were starting to sit down with their drinks when Chris said "leave the towel, why don't you just let the air dry you." I still wasn't entirely comfortable being naked with them, but I was thrown off balance a little by her request and left the towel and picked up my drink. As I approached my deck chair, Chris said "You don't need to sit right now. Just stand there for awhile. Your back and legs wont dry if you lay back in the chair." Chris has never been a demanding boss by any stretch as long as you do your job, but this kind of felt like she was exerting her authority a bit which surprisingly struck a chord with me. I had never been told what to do by a woman while naked and this caused a warm rush to suddenly come over my entire body.
I now felt Chris was in control, whether she was aware of it or not, and my penis instantly began to ache with excitement. Part of me was actually hoping Chris might tell me what to do next. I forget what we were talking about, but maybe five minutes later, I do remember Chris changed the subject and while looking at my penis, asked me "How's your love life going?" I said that I haven't had a steady girlfriend in probably three years. And she said "Do you think it has anything to do with the size of your penis? What is it, about four inches hard?" I replied with feigned pride, "four and a half on a good day." Chris then said "come here."
So I walked over to the side of her chair which would still be facing Gina as well and Chris reached up and rubbed the skin where my pubic hair would be and said I like this. I may have to try to get my honey to do this. She accidentally hit the head of my penis as she pulled her hand away causing my erection to bounce for a couple seconds. Gina then asked Chris "Are his balls clean shaven too"? Chris looked and said to her it looks like it. Spread your legs a little for me. So I moved my feet apart so there was space between my thighs, and Chris then reached up with her right hand lightly placing her fingers on my balls, slid them forward towards my rectum and told Gina they were smooth and removed her hand.
I was becoming so aroused by this seemingly casual contact and conversation that my first drop of precum started to appear and grow at the bottom of the head of my penis. Chris noticed and reacted like it was some food on the face of one of her children. She reached up and put three fingers lightly on the top of my shaft and ran her thumb from the bottom of my head up along the slit, then slid her three fingers down to meet her thumb so that she'd get all of it and then wiped her fingers off on her towel. She then told me "Don't get any on the deck. I don't think it would stain, but I just want to make sure."
I stood next to Chris as the conversation continued, and inevitably another drop was growing. Chris noticed and said "You take care of this one before it drops!" Well, I didn't have a towel or anything with me, so I did what I would do if I were by myself. With both girls watching, I reached down and collected the slippery liquid on my middle finger, brought it to my mouth and licked it off. They smiled as I did it, but made no comments about it. I've been a fan of eating my precum for quite some time. I actually enjoy the taste. I have tasted my cum a few times, but can't get used to it. After that it seemed like every two or three minutes I was putting my precum in my mouth.
Chris then said "I can't believe you've stayed hard this long. The next couple of times you wipe your cock, save the liquid in your hand." I did as I was told and with three or four good sized drops in my hand I was then allowed to finally lie in the lounge chair between them. Chris then said "I think you should spread what you have on your cock and start playing with yourself." I have masturbated for girlfriends in the past, and once, unknowingly at the time, in front of a neighbor I didn't know (another story for later), but never at the request of anyone else, but I was at the point where I would do just about anything for them.
Once lying in the chair, I put my right hand on my penis and started spreading my self-made lubricant on the head and shaft. Conversation stopped for the first time that day as Chris and Gina both sat on the edges of their chairs and silently watched. It was just a matter of seconds before we could hear the lubricated squishy sounds of my hand passing over the corona. Chris for whatever reason started to run her fingers through my hair. Maybe to let me know that what I was doing was ok? Gina placed her left hand on my thigh in a comforting gesture, just inches from my penis.
As I was masturbating, I thought about the revelation to these two sisters of the incredibly private secrets that I had kept to myself and my sexual partners my whole life, and the arousal I now felt knowing that these women now know I have a small penis and like to eat my precum. I wondered how Chris would treat me at work the next day. Would everything be the same after that day? Knowing them as I did, it probably would.
My body sensed, very much, the closeness of Chris and Gina to me as I continued to stroke. It felt like a very personal type of relationship was developing that only related to that moment, but may last a lifetime in our (or at least my) minds. Chris then removed the fingers of her right hand from my hair and replaced them with her left hand as she lowered her right hand to my groin. In a very soft tone she told me to spread my legs a little. We all seemed to be caught in the moment now. Chris gently cupped my balls and it felt great, but made me lose control of my stroking. I wanted it to last forever, but that contact made me stroke faster. She then turned her hand to the right and pushed her fingers forward until she reached my rectum. I'm not a big fan of anal penetration, but this was a unique situation.
So I slid down a little lower in the chair and raised my knees so that my feet were flat on the chair and I spread my legs apart a little more. I felt so much more exposed and vulnerable, and Chris understood what I wanted. I don't think she was planning on going that far, but along with Gina's encouragement to 'push it in', Chris started to exert pressure on my rectum. Her finger didn't have to go in very far when I started to squirt cum on myself and her hand and wrist. Once I had finished cumming, she raised her hand to look at what was on her and said "See if you like this too", and moved her wrist and hand to my mouth. I gave it a small taste, but then closed my mouth. Chris then, in a carefree sort of way, just gave a silly laugh and wiped what she could on my mouth and face. And as I was still catching my breath, I once again parted my lips and ran my tongue around them tasting myself for the final time. I've never had another experience close to that.