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Shy Guy Gets Laid

Age when it happend: 22
Where it happened: House of Prostitution
Langauge: English
Sex: Male
Rating: 10
Category: Straight

My first time was a pretty routine one, with a prostitute, but there is a little different angle to it.
This goes back to 1940. For those of you too young to remember, that was just before we got into world War II. (That was a big war between the U.S. and its Allies on one side and Germany, Japan and Italy on the other.) (We won)
I was a young college student and a virgin, for at least two reasons. One was I had high moral standards and the other, more important one, was that I was just ridiculously shy.
One week in July my cousin, Roy, who was a sailor on leave from the Navy, came to visit us. He was a little older than I, and very much a man of the world.
He wanted to have a night on the town so I called one of my friends more worldly than I to go out with us. We went out and had a few beers, while I drank cokes, and played some pool and then Roy asked where a man could get laid in this town. That was easy to answer because even an unworldly guy like me knew that those places up above downtown businesses that called themselves hotels were really whore houses.
My worldly friend said the Broadway Hotel was reputed to be the best, although a little more expensive, at $5. On the other side of the tracks you could get it for $1.50, but Roy said no, let’s go for the best.
So we went up the stairs to the Broadway Hotel, where the madam, a nice looking middle aged woman, greeted us and took Roy in to claim a companion. My friend and I sat down to a pleasant chat with the madam, but very soon Roy came out with his arms around two girls.
He said “This one,” squeezing the girl on his right, “is mine, and Susy here is for you, Tom boy.”
Susy, a quite pretty young woman in the flimsy attire of her trade, came over to me and said, “How about it, honey, would you like to have some fun with me?”
I was startled and shocked and really taken aback. My first reaction was to flinch away and say “Oh no, oh no.”
Susy said, “What’s the matter, honey, don’t you like me?” I said, “I’m sorry but I just don’t want to do this.”
Susy tried to put her arms around me and I pushed her away. It’s part of my memory of shame that I used my feet as well as hands to repel her. Then I said “I’m going back to the car,” and left.
Some time later Roy and my friend came out and as we were driving away, Roy said, “You know you made that sweet little girl cry.” My friend said, “That’s right.”
I said I was sorry but she had just taken me by surprise and I really did have moral objections to having sex with her.
Roy said, “Well, I told her she could keep the five dollars I’d already paid, so that will make her feel better.”
Roy went back to his ship the next day, saying nothing more about our “hotel” experience.
But I couldn’t get over feeling guilty at having made a girl cry, even if she was a prostitute. Two days later, in the afternoon I went back to the Broadway Hotel and climbed the stairs.
The madam said, “Oh, it’s you again. What do you want this time?”
I asked if Susy was in. The madam said “She is, but I don’t know if she’ll want to see you. But I’ll ask her.” She went into the back room and a minute later Susy came out. she was in regular street clothes, not her scanty working outfit.
She said, “Oh,it’s you. What is it, do you want your five dollars back.”
I said no, I just wanted to apologize for the way I had acted the other night. I said I didn’t mean to make her cry.
She said, “Did your cousin tell you that? That bastard, he wasn’t supposed to tell you.”
I said, “Well, he did, and I really feel bad about it, and I wondered if — if you would forgive me enough to give me another chance. I’ve got another five dollars.”
She said “I’ll be glad to give you another chance, but you don’t have to pay me, your cousin already did.”
I told her she could keep that five dollars as payment for my rude treatment, and I wanted to pay for my own first introduction to sex.
She said, “Oh, you’re a virgin. Well, that accounts for a lot. Come on in, honey, and let’s see what we can do about it.” She took my five dollars and we went into her room. She said, “I don’t have my working clothes on, but you can help me undress, since it’s your first time.”
So I had the happy experience of helping take her clothes off, and I mean all the way off, down to her bra and panties, and she let me take those off, too, giving me the most delicious thrill I had ever felt.
Then she did a very slow and gentle guidance of me into the ways of sex. She let me suck her nipples and fondle them, and to feel into her vagina and feel her warmth and wetness, and then she took my prick in her mouth and gave me my first oral sex, which had me in six degrees of ecstacy, and then she said, “Now for the dirty deed itself,” and I entered her and had indescribable pleasure as I went all the way in and then partly out, then back in and out again. She was gasping with pleasure, whether real or simulated I don’t know, and I was gasping with real pleasure, and she said, “That’s the way, honey, you’re doing just fine.”
Then it was time to come and that was yet another great new thrill. She gasped and trembled as if she were coming too.
Then it was over and she said, “Well, was it worth the five dollars?” and I said it really was.
She gave me a nice, sweet, friendly kiss when I left.
I went back to the Broadway again a few months later, but the madam said Susy wasn’t working that day. So I got Pauline, who was also a great sex partner, and she said she would give Susy my regards.
Then I got drafted into the Army and was away from home for four whole years. When I got back I went where the Broadway Hotel had been but it was closed and there were apartments for rent in its place.
I asked the man who ran the print shop downstairs and he said the hotel had closed when a new mayor was elected on a reform ticket. But during the war there had been both an Army base and an Air Base just outside of town so the hotel had done a huge business and all the girls had made enough to retire and some of them had married service men.
So I don’t know what happened to Susy, but she still has a warm place in my memory.

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