We got married when I was 39, and she was 51, We were both 2 time losers and met on a blind date set up by a friend of a friend. It was lust at first date, dinner at 8, in bed by 11. On our second date, we got laid before we went out! I was surprised to hear myself ask if she'd like a quicky before dinner and more surprised when she got up and led me towards her bedroom. We would not have left her apartment if I hadn't promised to go to dinner with a bunch of friends to celebrate somebodies birthday. This group of friends always had raucous dinners, lots of bartenders and waitresses, the booze would flow and somebody always knew somebody so we got great service and big drinks. With a party of twelve it was not unusual for somebody to get up and tip the bartender an extra $50. Needless to say When I left early with the new girl, comments were made. I even heard about it on Monday at work! Within a year we were so steady we gave up one apartment and six months later decided to get married. It was a great match, I was always oversexed and Sandy was the very first woman I had ever met that was always ready. Sandy was Jewish from this big family and I was this mick bartender that made sure his family didn't know where he worked, not your average marriage, but boy it sure worked for us!.
Back in the sixties I was tending bar in an office building and I got a lot of girls and women. The young secretaries and clerks that came in were like shooting fish in a barrel and there was an almost subset of 35 to 50 year old office worker that had sort of given up on love, they were either never going to get married or they had some shit marriage that they just put up with for the dual paycheck life style, and then there were the women who ended up sleeping with the boss for 5, 10, 15 years, never had a date on the weekend and had to make small talk with his wife when she called the office. All three groups knew I was a wastrel bartender out for nothing more than a good time and they used me accordingly. Once the word got around that I never talked, I was getting some at least once and sometimes twice a week. Our bar closed at 8 PM and I would hide them in the washroom till I got rid of the last customer. More than once the night porter walked in on me getting a blow job. I tried a couple of times but I never got any of them to do Jefferson, so I just had to tip him a little more that night. I'm giving you this background so that you understand when I say Sandy was always willing and wanting when it came to sex, and I was in a position to judge her uniqueness.
Well, back to my marriage, we were truly in love and the sex was great and as frequent as my dick would allow. Sandy and I hadn't been together very long when she was getting off by being ass fucked. I swear she got some sort of emotional cum from sucking my dick, it was a hell of a life. We would go to an occasional swap party on the weekends and once in a while I would do one of my bar regulars, but basically we were monogamous and I was starting to enjoy the straight life. I was even starting to like Sandy's youngest daughter; Jennifer, she was a math whiz, graduated from high school at 14, college at 16 had a master's in applied something or other that I sure didn't know how to pronounce, and was working at some advanced math lab while doing her PHD. I've since found out that a lot of gifted kids have emotional problems, with Jenny it was partially due to never having had a social puberty. Every boy she went to school with was at least 6 years older than she was and in addition she wasn't the prettiest peach on the tree. Almost anorexic skinny, acne, granny glasses and that bizarre sense of humor that seems to go with genius. All this added up to me being the step father of a 20 year old who occasionally had outbreaks of twelveishness. Fortunately for me most of those were tearful hour long phone calls to her mother.
Then one Saturday morning I heard those terrifying words, "Sit down, we have to talk." As I sat down I was doing a dual review: one, what had I done lately and two, what was a good excuse. As it turned out, it was a good thing I was sitting. "Jenny called last night while you were at work. We had a long talk about sex." I knew I was off the hook, I had never even thought about Jenny sexually. Now she had a couple of cousins..."Hey listen to me!" I refocused. "You know she never dates, and when she does go out with somebody it's a disaster. She wanted to know if we could help." Before I could say I didn't know anybody her age. Sandy continued, "So Jenny and I thought if you'd have sex with her..."
"What! Back up..."
"No look, Jenny thinks part of her problem is that she just doesn't know anything about sex, no she's not a virgin, she just has no experiences. She though that if you could spend a weekend with her..."
"A weekend, is this a gag? What..."
"Let me finish dammit! You and I go to those parties, Jenny doesn't know that, but she knows we have a lot of sex. She wants someone she can trust to take her for a weekend and teach her how to do everything. She can't ask a stranger, she's ashamed to admit how little she knows to any coworker or her sisters or cousins and she says she likes you. She thinks you wouldn't hurt her but would make her do all the stuff she should know."
"Hey wait, why does she think that about me? What have you been telling her, I've been real straight around her.!"
"Oh honey, I know you have; and I appreciate it, but she's my daughter, we talk."
"What the fuck you been saying?"
"I don't give her a play by play but I've told all the girls and my sister how happy I am and how good you are." There were two other girls, one was an out of towner that I had barely met, the other I didn't like, but hey it was a package deal. I started reviewing the sister in my mind, yeah that's doable. "Look. Like I said we go yo those parties, so you know I'm not jealous of you doing a different woman, I told you when we got married, that I didn't mind us fucking around with other people as long as it was open and we both knew ahead of time, just like I told you I was going to be your old testament wife, 100 percent yours, you're my man and you know I'll help you do other women, so now help me by helping Jenn. Come on or I'll start giving the phone to you when she calls on one of those crying jags."
"Jeez Sandy, she's awful skinny, what if I couldn't get it up?'
She laughed out loud, "You, who do you think you're talking to, I know you. Besides if your dick starts to let you down just remind it that you're doing your stepdaughter, that'll get you hard in a flash." I couldn't argue with that, I was a whore. As the conversation continued I discovered that this was just a courtesy, I was due at Jenny's apartment in an hour, and Sandy had already packed an overnight bag. "Don't worry, she promised me that she had your brand of scotch and laid in a 12 pack of beer for you. Now you go there and be nice to her, we got to get her a boyfriend."
"Sandy, just how far should I go, I mean with us, there are no limits should I..."
"Honey do everything with her, make her do it all, well, maybe not anal, she's real skinny but every position, make her swallow, this is a fantasy come true for my big jocker." And I got a big kiss with a lot of tongue, as I reached to grab her ass I got pushed away. "Oh no, save it for my little girl, tell you what, anything she doesn't do, you come home and tell me and I'll do it twice, and then call her up and yell at her for not doing it, how's that?" I was shoved in the shower and warned, "no playing" and then pushed out the door.
It was a twenty minute drive to Jenny's and looking back, Sandy had been smart to spring this on me with no warning. Back then the phrases 'friends with benefits' and 'booty call' hadn't been invented, so this was a pretty unique thing. I was alternately laughing because I was having trouble comprehending what I was about to do and trying to will my erection away. I was off to teach a twenty year old all there was to know about fucking! And my wife was happy about it!!!
When I got there I didn't have to worry about my hard on. My first look convinced me Jenny
had chickened out. Ugly cheap blue jeans, a flannel shirt and a bulky sweater, no makeup, her hair, combed, was the nicest thing you could say about it.
Jenny stood in front of me in the doorway, "Can I come in?
"Oh I though we'd kiss..."
"Jenn, I'm not back from the war, let me in, close the door and we'll kiss, OK" Oh shit, there went her eyes getting filled with almost tears. "Come on honey, let me take off my coat and then we can spend some time getting to know..." She helped me with my coat, pulled would be more like it.
"See that's the trouble, did mom talk to you, I mean I just don't know how this should go, should I..."
.... There is more of this story ...