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.
