I only had one more sexual experience with a woman in my fifties, and that was one I'd just as soon forget. I went to Waikiki Beach in Honolulu, Hawaii in the fall of 1988 and met a forty something Jewish woman from Pittsburgh, PA named Louise in my hotel restaurant. I saw her sitting by herself at breakfast for the first couple of days I was there. Since women by themselves are fairly rare at Waikiki (women seem to be usually with boyfriends, hubbies or girlfriends) I asked to join her at her table on the third day. Louise was friendly, had a nice sense of humor, indeed on vacation by herself so we decided to do some things together, starting by renting a car and taking a drive around Oahu island.
We ended up spending the next three or four days mostly together. Louise was hardly a babe, quite a bit overweight and fairly plain but she was fun to be with, a good companion for lunch and dinner (mostly with separate checks) and doing the tourist things with. We took long walks in the evening and talked of lots of different things. I think she said she'd never been married but had some ex boyfriends...but I'm not even sure of that. I doubt there had been much romance in her life, although I could be wrong. There wasn't much sexual chemistry between the two of us and I really didn't intend to try to get in her panties during our brief time together. It was sort of a brother-sister relationship. By ten or eleven o'clock we were back in our own hotel rooms by ourselves...except for that last night!
On the night before the day Louise flew home, we went out for some Mai-tais and other tropical drinks at some of the local night spots. We got a little drunk (to say the least!) I don't know what was in those Mai-tais but I got one throbbing hard on while we were still in the last bar! If it happened today, I would suspect somebody spiked my drink with a half dozen Viagra tablets! Louise started to look MUCH better to me and I had a sudden desire to bury my throbbing cock inside her! So much for the brother-sister thing!
As I felt Louise's tits and sucked her nipples I put my hand down between her legs and soon found she didn't have much lubrication there at all. I figured some expert pussy eating would take care of that so I soon had my face buried between her fat thighs. She seemed to enjoy that and soon became much more aroused as I continued to do my professional "yodeling in the canyon" act. After awhile, when my jaw started getting tired I moved back up so we could be face to face. I was hoping she would return the oral favor with some cocksucking but so far she hadn't even put her hand on my cock and that continued to be the case. I went back to pussy eating for a while!
I finally asked her if she wanted to fuck and she said we better not because she might become pregnant. I told her I had some condoms and she said okay but the tone of her voice told me she was not enthusiastic at all. I went into the bathroom and put on a rubber and rubbed some K-Y Jelly all over my throbbing cock. I still had "the mother of all hard ons"! I went back and tried to slip it into Louise but there was just "no way Jose!" I could get it in. It would have been easier attempting to stick a wet noodle up a wildcat's ass1 I never had that problem in my life until that night. I'm not sure if Louise was just tense or nervous or if she was in fact a 40+ year old virgin. She was still fairly wet, her clit became erect when I massaged it but no way I could get my dick in her. We would reach a point and she would say "Stop! It hurts!" and I would of course do as she said.
Finally I just gave up on trying to get my cock into Louise and took the condom off. I asked Louise if she would suck me off. I could tell by the look on her face she was not enthusiastic about that either. She sucked me (not very well!) for about 30 seconds and she stopped and told me she didn't like to do that. I then asked for a hand job and she started yanking on my boner, again not doing it very well but at least it felt better than doing it myself. I was starting to enjoy the manual stimulation when she stopped and laid down on her stomach on her side of the bed. She said she didn't want to do that either. SHIT! At that point I just gave up trying to get any sexual relief from her. I grabbed my throbbing boner and started jacking myself off. It didn't take long until I felt a powerful ejaculation approaching. I don't know what made me do it (blame it on the booze!) but aimed my dick at Louise's big fat buns and blasted a heavy load all over her butt and lower back. SPURT! SPURT! SPURT! It seemed like the mother of all ejaculations! There was fucking jism everywhere!!!
Louise was not amused and I can't say that I blame her. I can still hear her yelling with that New York accent "You bastard! You didn't have to cum all over me!" Even though she should have taken care of me, at least with her hand after all the time I had spent with my mouth and tongue between her legs, this was a rather rude thing to do, not characteristic of me at all. Blame it on those Mai- Tais or maybe that old saying "a stiff dick has no conscience!" I apologized but Louise was still highly pissed. She got up, went into the bathroom to clean off the cum and came back and put on her clothes without even saying a word to me. She did manage to gave me the finger right before she slammed the door on the way out. Her flight home was early next morning and I was glad I didn't have to face her anymore on that day...or ever again! I was too hungover to even get out of bed until late afternoon.
My whole point to this story is that sometimes sex in real life just isn't like it is in the movies. Sometimes it's lame, sometimes it's lousy and sometimes it just truly sucks (no pun intended!). I actually found that out when I was doing frequent one night stands way back in my thirties, but this was one of my more ridiculous sexual encounters and a pathetic way to end those sexual encounters of my fifties.
Sometimes you wish you'd just stayed home and jacked off instead of making a fool out of yourself in your quest for pussy! As for jacking off there was plenty more of that activity ahead for me too! We'll get to the final part of my sexual saga, bringing you up to the present, soon! Meanwhile thanks for reading...and to Louise wherever you are, sorry for my rude behavior in that Hawaiian hotel room! Aloha y'all!