This entry is part 19 of 25 in the series 2013 Mar

One of the perks of my husband being a doctor with his own private practice is the ability to role-play as a naughty nurse whenever the mood strikes. Like last Tuesday. Doug was working late, catching up on paperwork after the office closed, and I was in the mood to have some fun, so I dressed up in my favorite sexy nurse costume and went to surprise him.

I’d called ahead, wanting to make sure he was really alone, and knowing that we had the place to ourselves, I dropped my coat as soon as I’d locked the front door behind me. His office as all the way in the back, so I knew I’d be able to surprise him. I grabbed some empty files from the front and headed back to find him, calling out when I saw that the light was on in his office. “Dr. Doug,” I called, “I need your assistance in exam room three.”

“Gina?” he replied. “Is that you?”
I’d surprised him all right! I stayed in character. “Doctor,” I called again. “I need you in room three.”
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Boots Were Made for Lovin’

Chloe’s red stiletto boots came up over her knees and didn’t stop until they reached her thighs. The latex shone even in the dim light of the bedroom, and I was mesmerized. I’d paid some good money to have her come up to my room— her agency was charging me $600 for an hour of her time— but I couldn’t stop staring at those boots. They’d been eye catching when she was dressed, but now that they were all she had on, well, I can’t imagine anyone would’ve been able to take their eyes off of her. . . .

We spent more than 20 minutes just talking and flirting— with me ogling her boots— before she finally snapped me out of it and reminded me what she was doing there. But I wasn’t ready to just dive right in I needed more time with her boots.

Starting at the tip of her shiny red toe, I licked up her boot, polishing the already spotless latex with my tongue. I slithered my lips all over her calf and high up past her knee, then went back down and started all over, zigzagging back and forth as I went. My half hard cock grew stiffer as I worshiped Chloe’s boots, and soon I was harder than a lead pipe. It didn’t stop me from licking the escort’s latex thigh highs, though. I kept licking until I’d covered every inch of red rubber with my saliva, and then I moved further up her body and got into position to fuck her— finally.

As soon as I was positioned over her, she reached between our bodies and rolled a condom onto my cock. Then it was time to fuck.

My legs pressed against the slick latex boots as I lowered myself and thrust my sheathed cock into her cunt. She was wet, which meant she was turned on, and the idea that I’d aroused someone who had sex for a living made my dick throb. I pushed all the way into her, until I could feel her small patch of curls against my groin, and started to stroke in and out. I glanced at the clock as I fucked her, and when I saw that my time with Chloe was running out, I started thrusting harder.

I fucked Chloe with all I had, and I didn’t stop until I’d gotten $600 worth of pleasure. She came first, and I knew her orgasm was real because of the way her pussy spasmed and clenched around my dick. When I came a minute later, I filled the condom with my first load and then pulled out to spray the rest of it on Chloe’s boots.

While Chloe washed off her boots, I pulled on my boxers and grabbed my wallet. I took five $20 bills out for a tip and folded them, handing them to Chloe on her way out. It was definitely money well spent, and next time I’m in San Francisco, you can bet I’ll be giving her another call.— T.P., Shoreline, Washington

First Time Out

I have been a reader of yours for many years now. Although I like the straight letters, I much more enjoy those with a few kinks. I myself am a novice transvestite and am interested in the experiences of others.

My attraction to feminine clothes started when I was four or five years old. My mother let me play dress up in her clothes, but as I grew older I became more secretive about my fetish. When I was in college and in the years following I would occasionally buy myself a slip or pantyhose or some pretty thing. I would detest myself for putting these things on and masturbating. I would then throw them out, but in a few weeks I would go out shopping again.

It was on my first real job after college that I met Lynn, who became my wife within the year. We had a great romance and our marriage was equally good. My transvestite desires never did totally disappear, but I never dared to tell Lynn.

I always made a point to help my wife fold and put away the laundry. She has lots of fine lingerie and likes to be as sexy as possible. One weekend she had just brought up the clothes from the laundry room when she received a phone call. I took the clothesbasket into the bedroom and began to put the things in the dresser drawer. I guess I became too engrossed in feeling and arranging her panties and slips. I held one of her teddies in front of me and stood in front of the mirror. Then Lynn walked in and asked me what I was doing.

I immediately said I was doing nothing. She then said that I should stay away from her clothes and if I like those things that I should get my own. I couldn’t believe what I had just heard— first anger and resentment and then compassion and caring. I didn’t know what to make of this or how far to carry it. As it turned out, Lyn was in a talkative mood and told me that her brother liked to play with her clothes. She even used to let him borrow her things, but when he got older he would stretch things out or tear them or worse. I didn’t admit to anything at this point, so I just listened.

We had to do grocery shopping that night, and as I pushed the cart past the pantyhose display, my wife threw in two pairs. I don’t know what possessed me, but with a trembling voice I said, “What about me?” She replied matter of factly that I would need queen size, and threw in a pair.

After we got the groceries in the car, she said she wanted to go to the clothes store. “I don’t want you in my lingerie, so let’s get some that fits right.”

As soon as we got in the lingerie department, my pants started to bulge and a wet spot began to show. I tried to cover it with my coat. We picked out two pairs of panties, a padded bra and a very lacy full slip. My wife said that should get me started. I said I would wait in the car while she paid for the things. She pushed everything into my hands and said what a good idea, only she would wait in the car while I paid for them, and she left!

I was panic stricken. My dick went limp, my face flushed, I began to perspire and I thought I would faint. I somehow managed to get to the cashier. The woman in front of me was having problems with her credit card and began to complain loudly. Just what I needed. By the time the salesgirl got to me I could hardly speak, and there were two more women in line behind me.

As the salesgirl started to ring things up, she told me the panties were on sale— three for the price of two— and that I should get another pair. All I wanted to do was to get out of there. I said my wife had just left so I didn’t want to bother with it. She then held up my 38B bra and said it looked kind of big for that petite girl I was with. The woman behind me laughed. Somehow I managed to pay for my first set of intimate apparel and headed for the door very much relieved.

Halfway across the store I met my wife. She said she was watching me the whole time and had never laughed so hard in her life. She said she would have me buying garter belts, camisoles and high heels like a pro in no time.

I am in my late 20s, and that incident happened about three years ago. It certainly changed my life. I guess I’m one of those lucky transvestites who has a wife who also enjoys his hobby even if it is in her own way. Yes, she still puts me in embarrassing situations, but it is worth it.

Mr. E.M., New York

Good Things Come in Small Packages

I am writing in response to Mr. N.H. of Illinois, who is concerned about his five inch penis. I am a beautiful, blonde 20 year old woman. I love sex and think about it every minute I’m not having it. Unlike those crazy women who say thy love a big 10 inch cock, I go for the shorter men since they usually have the smaller cocks. I have talked with my girlfriends about size, and they agree that a smaller cock feels the best and is easier to handle.

One of my friends got up and left a man in bed when she saw that his cock was too big for her liking. I dislike big cocks they are sometimes very ugly and they hurt like hell when they hit my cervix. It is a real turn on to be able to fit the whole thing in my mouth during blowjobs. While fucking, a smaller cock can go all the way in without hitting the back of my vagina and gives the added pleasure of his balls touching my ass. I love to put my legs up and put my feet on my man’s shoulders so he can lick my toes and with a large man, this is out of the question.

I adore a small cock, and the little ones always satisfy me. The man I fall in love with, marry and have a family with will definitely have a bite sized penis.

Ms. J.B., Germany

Big Hilda

I got a kick out of Mr. J.C.’s letter in the August Forum, “A Raging Animal.” I can relate to it because I have had the same experience with my own wife. Hilda is a big Nordic blonde to whom I was married 10 years before we made a startling discovery.

Hilda had gone form 140 solid pounds to about 160 or so and her doctor told her to take it off. She joined a local spa to get some exercise and began to jog and reduce. As she lost weight and became more physically fit, our sex life, which had been somewhat on the wane, began to pick up. She started at the spa three afternoons a week, but then began to go on Wednesday evenings. It was the Wednesdays that were the most interesting.

When she came home those evenings, she would literally drag me into the bedroom to fuck my brains out. I found this a big turn on, and a bit perplexing because she had never been the leader in sex. This went on for weeks. I didn’t ask questions, I just enjoyed myself.

Then one Wednesday she came flying into the house, yanked me out of my chair, rushed me to the bedroom and tore off her leotard and shorts. She pulled my robe off me and began to suck my cock into hardness. She then impaled herself on it and began to pound her body on me like a madwoman. Then I noticed that she had a black eye and had red welts on her body. As we came to an earthshaking climax she yelled, “I did it! I’m the champ! I’m the greatest!” Then she fell on me, exhausted.

It seems that at the spa she met a female instructor who was into the martial arts, and had started boxing and wrestling classes for the women. Hilda had taken up boxing. They had trained with 16 ounce glove and no protection. From what Hilda told me and what I heard later it was a knockdown, drag out affair. They fought seven two minute rounds. Finally one minute into the seventh, Hilda had her opponent on the ropes, helpless, and was battering her badly when the ref put a stop to it. As Hilda related the story to me, she got all worked up again and we had another very satisfying session.

The upshot of this whole thing was that we took up boxing as a form of sexual foreplay. I got a set of 16 ounce gloves and we tried them out on the following Saturday. She was a good fighter and I had trouble defending myself that night. We have put a padded shag rug on our rec room floor and we go a few rounds three or four times a week with great sex following our workout. She goes to her boxing class once a week, but I don’t want her fighting for keeps anymore there is too much a chance of getting hurt.

I am five feet ten inches and 150 pounds. Hilda and I have some very good bouts but we are not out to hurt each other, just have fun. We’ve heard that other women box with their husbands and say they get good sex afterwards. One little girl, 105 pounds, gets on with her 150 pound man. He uses 16 ounce gloves and she uses 12 ounces. She beats the hell out of him and then fucks him into oblivion, much to his amazement. Hilda says that it seems to loosen her inhibitions and gives her a sense of power she never had before she took up boxing. But leave that for the psychologists to work out. All we know is, it is fun to have a boxing match. The sexual results for us are wonderful. This happened four years ago and is still a big turn on.

Mr. (Name and address withheld by request)