My wife had a good friend she had worked for for over 10 years. Jean was about 10 years older that me approaching 50..no to be kind I'll say she was very plain..had frizzy hair going grey, her figure is best described as barrel shaped..but what she lacked in looks she sure didn't make up with personality - she was loud, abrasive and loved to needle me in a semi good natured way and as far as wife knew she never had a boy or girlfriend in those 10 years and never talked about any in her past even back to high school so she might have still been a virgin!!
Anyway her and wife had lots of interests in common so they were best friends.. someplace along the way wife found out she loved to travel as much as us but hated to go alone so she started inviting her to join us. Usually it was ok, we had a timeshare with two bedrooms and would always try to trade for similar. But on a trip to Ixtapa, Mexico we had a jr suite which was a big bedroom with 2 full sized beds, living room and a kitchen .. in the wide open living room was basically a short loveseat that could be a bed for a child. We decided we had to share the bedroom with Jean so wife took me aside and said, "We can't have sex this week because of Jean in the next bed." I think aww SHIT. First few days weren't too bad, I got into daily routine of jerking off in shower and that got me through the day. But then towards the end of the week they found a quilt shop and went to look for fabric so I went to the beach - not nude or even topless but still lots of eye candy in small little bikinis. After they came back I took another shower and got rid of my erection again. That evening I had a few too many margaritas and so was horny, so after lights out and when everyone stopped stirring I tried to fool around with wife ..who of course was a little pissed at me being "over served" and then we still had the no sex rule because of Jean.. so even though I was disappointed, with the help of the alcohol I'd consumed I gave up and went to sleep.
Next AM I woke up early (just starting to get light out) with a raging hardon.. thought damn, be at least an hour before I can shower, can't wait that long, so looked around ..wife was sound asleep back to me, Jean was same way in her bed so I rolled to edge away from wife and closest to Jean's bed and after making sure they were both asleep started stroking slowly so as to not jiggle bed..found out couldn't lay on back because that did jiggle the bed so rolled over facing Jean, found a rhythm that worked and didn't jiggle the bed .. I didn't want to get cum on sheets ( wife would NOT have been happy!!) so uncovered, and had nightshirt pulled up to my chest and had grabbed my tee from floor to catch the dribbles .. looked again Jean still had back to ne so I closed my eyes as it was now light in bedroom to think about these two teens I had been next on beach...whacked off with a great cum all over and some on belly .. I opened eyes and there was Jean about 4 feet away big eyes watching. I thought OMG and covered up with sheet..she just smiled and rolled over again. She never said anything that morning but would catch my eye and smile that same smile.