The Pool ServicebyJustplaingifted©
I am writing about this at the recommendation of my therapist. It is a story that really embarrasses me to relate and something that I once thought only happened to women with manipulative older men; not the other way around.
Here's what happened.
I was in college-poor, struggling with the requirements of premed studies, attending a small college on a track scholarship. It paid my tuition, but little else and so I picked up additional work where I could. I'd seen the offer on a bulletin board for work cleaning swimming pools. It said I could set my own hours and that they paid top dollar. I called and learned that they desperately needed help and they would teach me what I needed to know. I started immediately.
At first it wasn't bad. Fresh air. Decent money. The company had contracts for some of the most upscale homes in the area and it afforded me the opportunity to hope that someday when I was a successful doctor all that could be mine too. I'd been at it a few months when one afternoon I'd gone to a palatial home straight from track practice. I didn't realize, but the owner was a woman whose husband was an alum from my school. They had been divorced for a few years and she had gotten the house. Another lesson learned. She was forty and not bad looking. Not exceptional either. She had short frosted blonde hair and green eyes. She had put on a few pounds since the break up, probably weighed 140 at 5-4. Had it not been for the breast augmentation she would have been nearly pear shaped.
I was working away when she opened the French doors to the patio and came out with a glass of water in her hand. It was a nice gesture. I was sweating, in just my singlet and shorts and I was still a little dehydrated from practice. She watched as I drained the glass and smiled.
"You look very athletic," she said.
"Thanks, Ms. Hayword" I said.
Now, it's important that I clarify something. I was very shy. Painfully modest in fact. I was 6-2 and weighed 180. I had stereotypical runner's legs-big thighs and defined musculature- and very low body fat. I also-due only to the chance of genetics- have a very large penis. That is not all it is cracked up to be, I assure you. Everyone thinks it is, but there are lots of downsides to it. I'd been kidded abut it by my team mates and when I was wearing running shorts I always made sure I wore a jock or I'd find that the betraying outline of my anatomy and its movement as I ran, led to some embarrassing observation and comments.
So when she looked at me and said that, I turned a deep shade of red.
"You look really hot," wouldn't you be more comfortable doing that in a bathing suit?"
"No, ma'am," I said.
"Aren't you polite," she said and then shrugged and smiled and walked back to the house. I went on with my work, but about ten minutes later, the intake on the pool started making noises that told me there was something blocking it. The only way to open it was to get into the water. I had just primed the chlorine and didn't want to get in wearing my uniform as chlorine could play hell with the material, so I walked up to the house and knocked.
When she came back, she was wearing a fairly small bathing suit herself. It probably had not seemed as small on her years ago when she was slimmer, but with her heavier hips and the added tummy she'd gained, the only part of the suit that looked remotely fitted was her top. The bottoms were tight and a Brazilian coverage so with her weight gain they were barely decent. She had obviously had a pretty large augmentation and her breasts were easily D cups. They had "settled" and so they hung heavily.
"Finished already?" she asked.
"No I was wondering if you might have that bathing suit you offered earlier. I need to get into the pool and check the valve," I said.
"Oh of course," she said. "Come on in and I'll get it."
I followed her in and down a hallway to a guestroom. She started digging through a chest of drawers and then said, "Here you go."
She was holding a very brief pair of speedo trunks.
I must have looked as surprised as I felt, because she said, "All I have here, sorry."
With a pretty embarrassed look on my face, I took them. There wasn't much to them at all. She didn't smile; just gave me a sympathetic look and said, "You can change in the pool house."
I really didn't see any other option, so I took the little trunks and walked over to the pool house. Once inside, I undressed and stepped into the brief suit and just like I had anticipated, it was minimal. It was low rise, well below my hip bones. The worst part of it was that while it fit me around the waist and covered my butt, when it came to the front my cock barely fit and the bulge was ridiculous looking. With my flat abdomen the bulge looked even more ridiculous.
I walked out and as I should have predicted, Ms. Hayword was seated on a chaise lounge. Immediately her eyes went to my crotch.
"My goodness," she said with a kind of half-laugh.
That simple phrase just went right through me. She could tell it humiliated me, I think, and I felt like diving straight into the pool. Instead I placed my track gear on the side of the pool away from the water. I slipped into the water and swam over to the intake vent. It was cluttered with some palm fibers and took me a good fifteen minutes to get them out.
Finally the sputtering noise cleared and I swam back and climbed out of the pool. Now wet, the suit was an even more obscene display of my anatomy. The head of my penis and the thick, wadded shaft in the constraints of my trunks stood out so that its detail and dimension were undeniable. I immediately started looking for my track gear so I could go change. Unfortunately my clothes were gone.
I looked around and saw them neatly stacked under Ms. Hayword's lounge chair. Having no choice I walked over feeling completely exposed and embarrassed. It didn't help that the whole time she was looking me over with a slightly superior smirk.
She could tell I was embarrassed. She could tell I was basically shy. She could tell, well-as I said in the description of the speedo-a lot of things about me.
I started to reach for my clothes, when she did something that was completely unfair.
She said "Scott" (not my real name) what would it take for you to wear those every time you cleaned my pool?"
I looked shocked.
"There is no way I would do that," I said.
"I'd pay you a lot more!" she grinned.
The offer, the embarrassment, and my being so off-balance from being barely dressed and now propositioned had me almost sputtering.
"Uh no thanks."
She then reached back and undid her top. Even though she was an older woman, and even though she had gained some weight, the effect on me being barely twenty-one was profound and instantaneous. The surging blood to my crotch made the speedo entrapment of my cock profoundly uncomfortable. The bulge doubled in size right before her eyes. With an almost victorious look she laughed and said, "Well now that is impressive... and undeniably flattering. I guess you really area boob man, huh Scott?"
The lycra of the suit stretched to its elastic limits and as my enlarging penis pulled it away from my waist, I began experiencing real pain.
She seemed to actually be getting off to that.
"Owww," I said and doubled over a little.
"Are you sure you won't wear that when you clean the pool from now on?" she asked and then started to unfasten her bottoms.
"Okayyyyy," I said pleadingly as she pulled them off exposing her neatly trimmed pussy.
At that moment I was in real pain and I untied the top of my speedo desperate for relief. My cock sprang up extending almost to my navel. Without the constraint of the suit, it filled out rapidly expanding to its ultimate length and girth.
Ms. Hayword was delighted.
"You must me half race horse," she said. "you run like you do and are sporting that thing. Oh my Lord."
I bent down, humiliated and my cock jabbed my abdomen as I grabbed my track uniform. Then, utterly ashamed, I ran with my big erection waving, toward the pool house. Making matters worse, I heard the happy and slightly smug laughter coming from Ms. Hayword.
There was nothing I could do. My erection was intense and insistent. Inside the pool house, I stroked it thinking of her naked body. It didn't take long until I exploded in a heavily roped ejaculation. The sensation was so intense, I almost blacked out. Sometime later when I had composed myself, I pulled on my workout clothes and left the cabana.
Ms. Hayword was still on the chaise lounge in her bikini. It was back on and the coverage was in place as though nothing had happened. The only difference was her slightly self-satisfied smile, that, and the hundred dollar bill she was holding. She waved it beconing me to come over. I walked up terribly embarrassed.
She held the bill out.
"Take it," she said, "you are going to be getting tipped a lot more in the future."
I took the money without saying a word.
"You know, that was the most flattering and fun experience I have had in years." She said. "Well, one where I didn't have to insert anything."
And then she laughed. I left her backyard holding the hundred and the speedo. I looked at the small suit, realizing that the next time I was there it would be all I'd be wearing. A sudden surge of embarrassment and powerlessness went through me. I didn't want to do that, especially when I thought about her mocking looks, but I knew I would. At the same time, inexplicably, I felt a surge of blood flow again.
This a true story and there is a lot more. If this is exciting or interesting to anyone, I'll keep writing.