Am I Still A Virgin??

Hi, this is a true story with the names changed to protect the players. I didn't write this with the intention of getting the coveted "Red H" this site awards it's special stories; but there is some hot sex in it. What I experienced was a safe-sex situation I had never thought of trying before the opportunity was presented to me. I wrote it mainly to inform the gurls that read these stories of another type of safe sex method available out there. it was great for me and something I'll be on the look out for again. Hope its a good read one-handed.....:) Kelli

*

I'm a middle-aged, married, bisexual, semi-passable CD (I hate the words 'non-passable'). I've dressed for a few years, but for a multitude of reasons have never had anal sex. I saw an ad in Craigslist (CL) that seemed perfect for me. It ran in their Casual Encounters "m4t" section (T means TG/TS/CD, etc. - although most of you reading this do not need an explanation because you probably live and brush your teeth in this category...lol)

The title of the ad was "Mature Man Seeks Fem To Dress". The text of the ad was long and detailed but the premise was this...

A mature man with ED (Erectile Dysfunction) wanted to take a fem guy, strip him down, dress him up in lingerie and then fuck him with a strap-on. Making out, petting, foreplay was all to be part of the scene and of course fucking.

It took a couple of back-and-forth emails for me to feel comfortable with the guy and him with me. His picture showed a tan-faced guy, 60+ years, who was taller and bigger than me. This is usually what I look for. I don't know about you other CD's who are reading this but with me, playing with a bigger guy just brings out that hidden submissive nature I possess even more.

The guy (I'll call John) thought he'd hit the jackpot with me because not only was I fem, I was also a practicing CD to boot (I'm mostly smooth - except from the knees down). In the beginning the knees-down thing was a problem for him but I sent him a pic of me in textured stockings and he decided I would be okay for what he wanted to do.

A couple of things helped me. First I don't think he had that many responses from other applicants; and if he did, I don't think the responders fit the body size he was looking for (me: 5'9", 145 lbs, trim, athletic body). The second thing was he was really excited to hear I was an anal virgin (except my wife's dildos).

Through the back-and-forths I learned that John was married, a businessman and had had ED for a few years. I had limited knowledge of ED when we first started our communications, but Wikipedia helped me to realize that ED has a quagmire of reasons for making it impossible for a guy to get an erection. In John's case even drugs wouldn't get him hard. I'll just say that between John and I (Kelli by the way) it was a subject that we didn't talk about, other then we both knew it was our purpose for meeting.

We were to meet at his office, which he explained was very private and he was insistent that I stay at least 2 hours. He explained how he ran a specialty wholesale business and that he would be the only one there that day. I felt okay with the setup so I agreed and the meet was on for the next week.

I don't know about the rest of you gurls out there, but for me it usually goes like this. I hook up with a guy on the internet. We agree to meet somewhere (I never host). I walk in the door as a guy, head into a bathroom or bedroom as soon as I get there. Change into my girl clothes and then come out to play. About half the time when I come out as Kelli the guys are already naked.

I'm sure this type of insensitive guy-behavior would appall most women, but I actually love it. Any gurl will tell you that being a slut is a big part of what it's all about for us. And what says you're a slut more than being with a guy who doesn't care about talking to you but getting at you right away. Am I right...or am I right gurls?

So anyway this "strip down" thing had me a little nervous since I had never done that for a guy before. So a couple of days prior found me standing in my living room pretending I was stripping off my clothes for a guy while listening to music. Those real girls who make their living doing this for dollar tips will never have to worry about me cutting into their profits. I have bad rhythm and bad hip action, but I figured John wouldn't care how I got naked, just that I would.

His office was indeed private. It was located in a commercial office-warehouse strip building, the kind with no windows and loading docks in the rear. Most of the spaces had pick-up trucks outside, but the address I was supposed to go to had a brand new German luxury car outside. I knew the type; they retail over $100k.

I was on time and John greeted me at the door the moment I opened it. He was just like his picture (which anyone who uses CL for hookups knows this happens only 30% of the time). I don't know about the rest of you gurls, but I am never attracted to guys physically when I'm a guy. Their size sometimes yes, their faces never. And this time was no different.

We shook hands and he led me into his office. It was not what I expected. There were thick richly colored Moroccan rugs spaced out throughout a large wood paneled office. There was a large desk, plush black leather executive chair and a few antique wood filing cabinets. Along the wall was a big leather couch of camel shade. The room screamed money and class.

"Get naked for me, I'll be back in a few minutes. Do you need a bathroom first?" John said directly.

His 'get right to it' attitude surprised me a little, but when he handed me a new package of stockings before he left, it made perfect sense. The knees-down thing was an issue that he figured out how to deal with. I was actually relieved I didn't have to do the 'Gypsy Rose Lee' thing anyway.

When I use CL I hate the back-and-forth emails that the site breeds, so I always tell guys if it starts turning into War & Peace I'll move on to my other prospects. With John we had never discussed how fem I was going to be, just that he was going to dress me up.

I had my travel bag (all us gurls know what this is about) it's 'total gurl' in a bag. Those that live with wives or girlfriends have to hide it, those that don't are just fucking lucky as far as I'm concerned...lol

I stripped, opened the package and put on the Stay-up Thigh High black textured stockings. I'm shaved from the neck down and running my hands from the stocking tops up my ass gave me an instant hard-on. I wanted to give him more than Kelli in stockings, so I pulled out a flowing blond wig I have, put on some lipstick, a little scent (jasmine) and then took out some lube and lubed my pussy. Yea I know it's my asshole, but we call it a pussy...lol

Any gurl will tell you that you have to pre-lube before you meet with any guy. Usually when a CD is with a guy it doesn't take more than 2 minutes before the guy will have his fingers in your ass....oops, pussy. But as I said before....no worries, we're sluts and we love that.

John knocked and I opened the door. I could tell the addition of the wig and jasmine had its affect.

"Wow, you are hot Kelli."

I hear this statement a lot and love it every time it's said. "Thanks, you're looking good too."

John had stripped off his shirt, his bare chest showed gym-time and the gray hair on his chest was light not heavy (I'm not into the real bear-types). He had on a pair of jogging pants; I could tell the strapon was underneath.

This was "The Moment"....

In this case all I've put on is a wig and some stockings; but that's all it takes to turn on some switch inside me. It's the 'gurl switch' and I love when it's on.

It's that moment when I transform from the guy-me into a submissive, slutty gurl. A gurl that was hidden within me, but came out to play a few years back. Nowadays I'm happy every time she appears. It's a transformation of psyche from guy to girl. I can't explain it, didn't know I had it until a few years ago, but luckily I didn't suppress it.

It's also the moment when men become attractive to me. Looking at John's chest, shoulders and stomach the whole package suddenly becomes appealing to me. I become almost animal in my hunger to devour it. I know that's weird prose in explaining it; I think you have to be of TG/TS/CD nature to understand it.

Even though I wasn't as fully dressed as John probably wanted me, I went to him put my arms up around his neck and bent my head to lick one of his nipples.

"Oh god," he breathed. His arms went around me, his hands dropped to my ass and I felt one finger slide between my crack and then I felt the pressure of him pushing his finger into my pussy. (Less than 2 minutes, everything felt normal). His nipple hardened and I nipped it a little.

"Ouch," he yelped and pulled back a little.

Shit...CL emails can't tell you everything about the guy you're meeting, unless you exchange emails for weeks. So how's a gurl to know what a guy likes if you don't try it, right? Personally, my nipples are hard-wired. You can pinch, twist, pull, bite, and be however rough you want; as long as there's no blood, there's no foul.

"Sorry." I said sheepishly. I was sort of sad I had broken the mood, but there was another purpose for me being there and maybe it was a good thing it happened.

On his desk were some candles I hadn't noticed before and he lit them and turned off the lights. The way the candlelight played off the wood walls and furniture gave me a real sense of calm.

"Kelli I bought you some presents." He said as he went to his desk. He reached under the desk and pulled out some pink gift boxes. I didn't have to look at the name on the boxes to know they were from Victoria's of course...and today she was certainly keeping a secret.

He proceeded to open some of them up. Now for a gurl who usually shops at Walmart and Goodwill, this was a real treat. In our emails he had explained he wasn't going to give me anything that I wore. I couldn't tell, but everything looked new. I've been to VS before with my wife and I know the difference between their cheaper lingerie and the more expensive products they sell. This was the good stuff. And even though I knew he didn't buy them with the intent of a gift, it was cool to think he bought them thinking of me in them as he shopped.

"Let's start with this," he said as I saw him pull out a silk black garter belt. From the back I felt his rough hands working to attach the belt. I figured I wasn't supposed to do anything so I stood statue-still. After he hooked it, his hands started caressing my ass, the softness of his touch soon turned rougher. He pulled my head back gently and whispered in my ear, "I can't wait to fuck you Kelli."

A little segue here....All us gurls chose a name for ourselves, just like strippers do. To us CD's the name is like a trigger. The moment we hear it, it triggers the woman hidden inside us. For me I can't hear my name enough when I'm with a guy. But to hear it breathed in your ear with your ass being fondled and then have this deep sexy voice say 'I can't wait to fuck you'....well that was new to me. You see prior to this it's always been on the table that I don't do anal. This is the first time I had ever heard my name said, using "fuck" in the same sentence, from a guy I was going to let fuck me. It was spoken with such a force behind it. I knew it was only going to be a fake cock that was going to do me; but I thought, 'oh fuck, this is just way too fucking cool.'

Soon his hands stopped and he dropped to his knees and clipped my stockings to the garter. He lifted my feet and he slid up a pair of panties that felt nothing like my previous Walmart purchases. I could tell he wanted me to help so I adjusted my hard cock into them. The feeling was amazing. I told myself from that moment on, Walmart would never see my cash for another pair of panties as long as I lived.

"So pretty, so pretty," he kept saying and the whole time he's behind me rubbing my legs and ass. Soon his hands came around and started stroking my cock on top of my silk panties. Can I just say here...way cool.

Next he brought out a bra.

Another segue here....I never wear a bra. First off I have a trim athletic body, my pecs are fairly firm and big from staying in shape. My pic on this site will show you the types of tops I always choose to wear. I have a little hair under my arms and these types of tops are perfect for covering it up. I always tell anyone I play with that, 'what isn't smooth is covered - but with your cock in my mouth will you really care anyway'.

Recently I've taken to wearing just button down shirts and tying them up, like young schoolgirls who like to show off their hot taut bellies...Britney style. I don't button the shirts so the top bulges out naturally when you do this. This type of fashion method gives the guy I'm with easy access to my hard-wired nipples. What can I say; I'm a selfish pleasure-slut.

I lifted my arms as John slipped on the bra. I could tell it didn't fit the moment he tried to clip it. He could too. Shit, I thought.

"I have another one Kelli, I didn't know what your size was going to be so I have others."

'Others', I was really starting to like this guy.

The second one fit better. It had about a B or a C cup I couldn't tell, actually I wouldn't know the difference to be honest. But it fit tight around my chest, but not too tight. I looked down and I could actually see a little cleavage. I guess they don't call them Wonder Bras for nothing? Don't get excited gurls, I still looked like a guy in a bra.

"Here Kelly, these will help."

He placed in my hands two jelly-like breast forms; I think they call them. A first for me again. These were not the big ones I've seen at drag shows. They didn't have nipples and were only about the size of one sock rolled up. I started putting them in trying to arrange them so they would fit inside without them showing, but it was no use. The weight on my chest felt cool though. I looked down and liked the overall appearance it gave my chest, but there was no pulling off I was still a guy trying to play-act a part.

Without asking I went to the door and opened it about one inch. Then I went to the candles and blew them out. The room was near darkness. As all us gurls know, near-darkness is a gurl's best friend, even if they own a dog.

I could tell John approved because when I turned around he took me in his arms and brought his lips to mine and kissed me. The kisses were soft to start but soon our kisses became deeper and our tongues danced. I could feel the strap-on. Way cool.

Shit, another segue, sorry.....When I first started dressing I never kissed. In fact the thought of it could kill any hardon I had. But one day in the right bed with the right guy, I went along with a few kisses from the right guy. I had told him my ground rules of no kissing but he was persistent and I tried it anyway. He was nice what can I say?

It took only a few seconds and then is was all tongues and heat. After about 2 minutes I was the one doing all the kissing, I couldn't get enough and still can't. Suffice it to say, I love to kiss and be kissed by men when I am dressed. Now when I hook up. I only meet men that like to kiss -- no options.

John knew this, and to a guy who can't get an erection I would imagine his pleasures have to come in other ways, so kissing is important to him. One thing I knew for sure, I was into his kisses. The whole time we're kissing he's got his hands everywhere at once, including the occasional finger-fuck thrown in for good measure.

Some guys kiss but are shitty at it. Some guys do it just as quick-foreplay before they shove your head to their cock. But the occasional guy comes along who kisses with a passion that comes from some deep internal need to become one with you. This was the way John was kissing me. And I was kissing him the same. Dressed and kissing, it doesn't get much better.

His strong bare upper body was turning me on. My fake breasts were pushing up against him pushing back to occasionally give my own nipples a lightning bolt shock. My panties were soaking with precum. Every once in a while he'd push his waist towards me so I could feel the fake cock he was wearing.

Weird now to think about that? Here's a guy who can't get it up any longer but when he could, I'm sure he use to grind his hardon into all the women he ever kissed just like he was dong with me. Real or not I guess it's instinctive.

"John you are making me so hot. Please I think it's time to fuck me...couch please?" I stated this like the true bitch in heat I was.

I can only remember four times in my life when I was lucky a girl chose me to let me take her virginity. Once it happened in the back seat of my car. One time it happened on a blanket out in the desert (I live in AZ). Once it happened in my waterbed. And once it happened in the girl's parent's bed. She said afterward that that's how she always envisioned it.

The thing is, I can only remember the missionary position being how we did it every time virginity was involved. After I graduated from HS there weren't any more virgins around so that phase of my life is gone for experimentation.

If any women are reading this, I'd love to get their feedback on which position they were in when they lost their virginity. For some reason, I wanted John to take me the first time with me on my back, his tongue down my throat and me looking in his eyes. The doggy-style thing could happen another time. I guess I'm just a romantic as well as a selfish pleasure-slut...huh?

"Not yet baby," he said.

I love it when guys call you endearing names. I know when I'm with women as the guy-me, whenever I'm in heat and ready to fuck I always call the girl a cute little name. I don't do it on purpose, it just comes out. The hotter I get sometimes the names change. What can start as baby, can become slut, bitch or whore sometimes? If they swallow, the names get even cruder. It's all in fun and all blurted out in the heat of the moment. It was cool to think John was this excited even though he couldn't get it up.

"I have one more thing for you to wear."

In the last box he pulled out what I can only describe as a baby doll nightgown. Black in color and mostly sheer, but with little patterns woven into it. It was too sexy for words. He dropped it over my head. There was enough material up top to cover the bra and breast form imperfections. And it clung to my waist and hips tightly and ended up just barely covering my ass.

I can remember when I'd go business suit shopping. You'd try on suit after suit jacket, and then you'd put on one, and you felt like a million bucks. This nightgown was like that. Magical almost.

I threw myself into his arms and kissed him with such a passion that I think it pushed him off his game. I was the tiger now and he was my prey.

Some men even though they're Tops, like to have an aggressive playmate. And then there are Tops that like to be in control all the way. John was the "control all the way" type of guy. I think he was taken aback by my new assertiveness.

I could feel his body language change and luckily I channeled myself back quickly. I made my kisses softer until I felt him start to press back like he was the boss. Whew...that was close.

He led me to the couch.

"Baby, do you want something to drink?"

"Ah, what do you have?" I asked.

"The bars over there, why don't you make me a Scotch neat, and get whatever you want for yourself."

I suddenly realized now that he had me dressed we were going to go through the whole seduction scene process. At that moment I had never felt more like a woman. I found his lighter and lit the candles and shut the door. I wanted to see myself better and also wanted to have John see me now that he had me fully dressed.