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Cuddly Bear – and How a Joke got me Laid! (on a 1st date with Robin)

Age when it happend: 24
Where it happened: At HER Apartment, after our 1st Date!
Langauge: English
Sex: Male
Rating: 5
Category: Straight

I was raised in a religious (Jewish) home, which meant that I was taught that to even touch a girl before marriage is not allowed. Of course, what you are taught and what you do, are often two different things.

Other than hold hands, I never really “touched” a girl till after high school. In college I learned to make out (“religious” girls taught me, which was pretty cool), and although I got blown a couple of times, climaxing in sex was not the norm, and I never got to “intercourse” and didn’t really expect to do that until marriage…..

I dated only within my faith and never even thought about dating a non-Jewish girl. Although I’m not a hunk at all, I have an extremely warm and outgoing personality, I am an amateur comedian, and lots of people fixed me up on lots of blind dates. (By the time I married my wife at age 28, I had dated over 300 women!)

I got close to getting engaged a number of times and actually did get engaged, and had a wedding date of August 24, 1974 set, before we broke up and it was for the best.

In the summer of 1976 (I was 24 at the time) I was not dating anyone in particular and when I decided to take an “in-the-city” (stay at home) vacation, I asked out a couple of non-Jewish friends from work to share with me the list of movies and plays I wanted to catch up on during that vacation in NYC.

The second girl was Robin. Robin was the most beautiful/sexy girl in the entire company of over 200 people. Although a little heavy, she really looked “zaftig” (yiddish for voluptuous or Rubinesque). She had long strawberry blond hair, a wondefully charming smile, huge knockers, etc. She was the only gal in the office that guys talked about behind her back as to how they’d love to nail her. Everyone said that they thought she’d never give any of us a try. I had befriended her and we spoke often at the coffee machine, and I screwed up the courage to ask her out to dinner and a play – and she said YES! I was the envy of all the guys. I could NOT believe my good fortune myself.

Dinner went wonderfully, and as we sat down at the play, in conversation I happened to mention one of my favorite lines from comedienne Elayne Boozler: “I can’t understand hookers. I mean, how can ANYONE go to bed with a guy without him buying her dinner and a movie first!” I thought it was a great line, and we both laughed.

After the play, I took her back to her apartment, and she casually invited me in. We kissed a bit and made out and then (I hope I remember this right… it was sooooooooo long ago!) I believe she told me she was getting undressed and I should do the same….. WOW! I couldn’t believe my good fortune! This was IT! It was going to happen! I was gonna get laid! We stripped down and made out some more… and she excused herself to go to the bathroom to insert her diaghram. It took her forever to come back out, (I even lost my erection in the interim) but when she came out of the bathroom, I was really able to see her whole body for the first time and she was stunning! Especially those huge tits of hers! She lay down on the floor, and I started sucking on her tits, inching my cock further up her body (I forgot to mention that she was about 5 years younger but three inches taller than me). Anyway, I admitted to her that I was a virgin, and she told me to relax and have a good time and to just do what comes naturally and to worry about my own pleasure and not hers. This puzzled me, but I decided to go to town on her! I got my cock inside her and starting pumping for all I was worth! I was quite surprised at how “roomy” her pussy felt, (I later described it as sticking my dick into the Lincoln Tunnel and trying to get some “friction” going!,) but I did know that she had been terribly active sexually and seemed pretty “stretched out” from (probably bigger) cocks. Eventually, after a bit of a struggle, I did cum hard inside her. After recovering from the shock of the explosion and my “first time,” I got out of her, cleaned myself up, got dressed, kissed her, thanked her profusely, and left her apartment, walking on cloud 9! I looked at my calendar watch to try to remember the date – and just smiled. I would NEVER forget it! It was August 24, 1976 – exactly two years (to the day) after I was supposed to get married (and get laid for the first time).

In a conversation with Robin later on, she explained to me that she had been so “selfless” about sexual gratification for herself, because she had had terrible luck/experience at cumming and had only orgasmed with a partner three or four times although she had had sex over a hundred times.

If you believed everything until now (and you should – it is the absolute truth to the best of my recollection) the next part will make you skeptical. Because as I am having mixed feelings about what I did as feeling good, but so guilty in the eyes of my religion, five weeks after we did “it,” Robin comes to see me at work and asks if we can go out during lunch to talk. (This is so cliched as to be hard to believe!) Sure enough, she tells me she’s late in her period, later than she’s ever been before, and is worried that she is pregnant – especially becasuse she had so much difficulty inserting her NEW diaghram for the first time!

I, of course, was shocked, upset, and on the verge of tears. I was sure that God was punishing me for this one transgression! I HAD INTERCOURSE ONE TIME – AND NOW I WAS GONNA BE A FATHER – WITH A NON-JEWISH GIRL I COULD NEVER MARRY! What a fine mess I had gotten myself into! I couldn’t even imagine HOW to bring up the subject of abortion with Robin….

Anyway, the punchline is that after sweating it out another 10 days, she got her period! Phew!

And the next time I had intercourse was on my wedding night (I was so scared from THAT experience!), June 15, 1980 – nearly four years later!

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