A Long Cool Woman in a Black Skirt

I first saw her in the lobby of the hotel in which I was staying for my conference. I'm the national sales manager for a large manufacturing company. We hold a national sales meeting every year to which all of the regional managers are gathered for education on new products, sales techniques, etc.

She was a tall woman, actually taller than I, but I noticed she was wearing heels, pretty black strappy sandals that put her a couple of inches taller than I. Her face was classically beautiful, her curly hair, wavy down to her shoulders framed her face beautifully. She used her makeup subtly. I can tell when a woman knows how to use makeup professionally. She knew what she was doing.

She wore her crimson jacket open, framing her nice breasts under a black silk blouse, unbuttoned just far enough. She wore a black leather pencil skirt that hit a few inches above her knees. I was happy to see she wore nice stockings. I didn't see any garter bulges, so she either had on thigh highs, my favorites, or pantyhose. I suddenly wanted to find out which.

To me, though, the most interesting thing about her was a definite bulge in the front of her skirt. She looked very feminine, but she didn't mind displaying what she had under her clothes, either, and I was very interested.

I'm bisexual. To me, the most interesting girls are those who have extra equipment between their legs. I began to get that lovely warm feeling down below and I could feel definite growth potential in my boxers.

She noticed my scrutiny and my interest. Smiling, she walked up to me and proffered her hand. "Hi, Bill, I'm Lori. I work in the Kansas City Division."

I grinned and squeezed her hand warmly. "Hi, Lori, it's nice to meet you! You're new. I haven't met you before."

"This is my first sales meeting."


"I hope you're having a nice time."

"Yes, I really liked your talk on customer expectations and service. We need to do more in that department out in K.C."

"I'm glad you took my talk to heart. If we treat our customers better than we would expect, they'll be ours forever."

We chatted for a bit and I was impressed by her in a number of ways. Firstly, she was quite intelligent. Secondly, she has a wonderful sense of humor. Thirdly, she seemed to find a couple of opportunities to touch my growing member and make it harder.

The group with whom I'd planned to go to dinner arrived and I invited her to join us at a nice steak house nearby. She smiled pleasantly and agreed to come along. We all piled into a cab and, for the next ten minutes, her thigh was right against mine. I found her perfume very sexy. I wanted to take her to my room right then and have an in-depth sales meeting, but I had to be patient.

By the time we cabbed back to the hotel, we'd all had a few drinks and some wine and I was definitely needy. As I got out of the cab, I offered my hand and she smiled as I helped her out of the car, casually letting me peek up her skirt. To my delight, she showed me thigh highs and red panties. I just couldn't resist the temptation.

I whispered, "Would you like to come up to my room for a little while?"

She looked me right in the eyes. "I was hoping to come up to your room for the rest of the night, Bill."

We got into the elevator and rode up to her floor. I passed her my spare room keycard. "Room 2214"

She palmed it and walked off of the elevator without a backwards glance.

In my room, I ordered a bottle of champagne and a bowl of strawberries. I got a few important things out of my luggage to put on the night stand, condoms, lube, a butt plug, and a pair of handcuffs. I got the impression they might come in handy during the night.

I took off my jacket and tie, but I left the rest on in case she enjoyed undressing her dates. A little splash of my favorite cologne and a comb through my hair and I heard the door unlock.

I was happy to see she hadn't changed. She'd refreshed her makeup and dabbed on a little perfume. I think leather skirts are amazingly sexy on a woman, but I don't like great amounts of perfume. She understood the principle. She'd used only a little bit.

I stood to greet her with a hug. She definitely had the same thoughts in mind as I. She melted into my arms and held me closely. I loved the feel of her breasts against my chest and I let my hand wander to her waist and then below that to caress and then cup one of her ass cheeks through her skirt. She gave a lovely little moan and squirmed her lovely bulge into mine. She was definitely erect and hard as nails, just as I was. I held her in the clinch as we slowly rubbed against each other.

When we broke the kiss, she gave me a lovely smile. "You give good hug, Bill."

I grinned. "So do you, Lori. You're a beautiful woman. I absolutely love your perfume. You smell heavenly."

"So do you, dear. I so love the smell of a man who knows what he likes."

I took her hand and led her to the couch in the sitting room of my suite. The refreshments were laid out there for us to enjoy. "Would you like a glass of champagne?"

"I thought you'd never ask. I'd love one."

I took a moment to remove the wire and covered the cork with a handy little towel. As I slowly worked the cork out, I saw her smile appreciatively. "I'm glad you know how to open a bottle correctly, dear. Letting it shoot all around the room is such a waste."

Putting the cork aside, I carefully poured two flutes of bubbly and handed her one. I sat next to her, our thighs touching. I let my left hand touch the front of her thigh, through her skirt as I raised my glass to toast her. "To you, a very lovely girl."

She actually blushed as we clinked glasses and smiled appreciatively. "It's not too often I find a gentleman who appreciates girls like me. To you, dear, with thanks."

We drank again and began to relax. "I've always liked pretty girls like you, Lori. Ever since my best friend in school tried on his sister's cheerleader outfit and I realized how sexy my friend was."

She smiled crookedly. "Was he your first?"

Smiling in reminiscence, I confessed, "Yes, though not that time. He and I had learned how to masturbate together and we spent a lot of time looking at girly magazines, getting horny to the point we'd have to do something about it. After our first time jacking together, it took about six months before we started jacking each other.. My favorite times were when he'd try on his sister's clothes. I learned just how alluring a guy in a dress could be.

"It was later, in college, I discovered my attraction to transsexual people. I'd already figured out I was bi and the fun two guys could have together. The first time I had a real date with a trans girl, I was hooked. I think I'd marry one if I could find the right girl. Half of my enjoyment in the trans girlfriends I dated was their obvious love of being feminine. That fed my libido nicely and I look for opportunities whenever I can.

"I was so delighted to meet you today. I'm amazed our company would hire a trans woman, but I'm happy we did."

She chuckled and kissed me. I happily returned it.

"I don't think the big bosses know I'm trans and I want to keep it that way. Usually, I wear a very effective gaff and I dress very professionally. I really do like my job and I do it well. My sales record was tops two of the four quarters last year. It doesn't hurt to have a girl who understands machinery selling and it really helps when I wear a short skirt or leave an extra button undone on a sales call. I'm all business, though, and I do a good job demonstrating our products and helping the customers in their final applications. I'm really good at what I do, Bill."

I grinned evilly at her. "I certainly hope so. I definitely want you to do me tonight, darling."

"I'm so glad. The first moment I saw you, I wanted to get to know you better. I just had a feeling you might like a girl like me."

By way of answer, I turned toward her and pulled her closely for another kiss. She is so gentle, she kisses like a girl and that fits my dreams and desires perfectly. I wanted her.

In every way, she was just a perfect woman. Her face, her voice, her mannerisms were all unconsciously feminine and I totally approved. I spent considerable time kissing her face, her cheeks, and her neck. Definitely a good spot for her, I kept that in mind in the file where I catalog the erogenous zones of my lovers.

It wasn't long before we were unbuttoning each other's tops. She had on the prettiest black lace bra. I was thrilled to discover her cups overflowed with very natural breasts. Her nipples came to attention as I slowly caressed and then leaned over to kiss them. I was happy to note that her nips were deliciously sensitive and seemed to increase her arousal.

I had to know and almost kicked myself for asking, "Are you on hormones, my love?"

She seemed to read my mind. "They're natural, dear. I take estrogens, but my breasts just grew like this. I'm a 36DD. It seems to run in the family. All of the women are well-endowed. Do you like?"

I'd managed to work her blouse off of her shoulders and I was working on unbuttoning the cuffs. She relaxed and just let me work. Once I got her blouse off and set carefully aside (I didn't want to ruin such a lovely blouse. I wanted to see her wear it again.), I ran my hands over her bra. She definitely liked that.

A little pinch of her nipple earned me a little squeak and a moan from her. That turned me on even more. I slipped her bra straps off of her shoulders and peeled the cups off of her breasts which were delicious. I spent a half hour at least worshipping her mammaries. She enjoyed it as much as I did, so I didn't feel compelled to go any faster.

Eventually, my basic lust kicked in and my hand moved to her knee, just below her skirt. She seemed to like that idea. Her legs parted for me, as much as her tight skirt would allow, anyway. I accepted her invitation, slowly caressing her inner thigh. She seemed to enjoy the feeling and renewed her kisses.

She was undoing my belt and unzipping my slacks as I felt her up under her skirt. I was happy to discover a rather nicely shaped cock in her panties that twitched as I gently stroked it with my fingers.

I wanted more, though. "May I take your skirt off, darling?"

"I thought you'd never ask. Please do."

She stood up and I knelt at her feet. I hugged her hips and gave her a kiss through her lovely skirt. I couldn't resist taking a moment to caress her ass and squeeze her delightful globes. She seemed impatient, though. I forestalled her reaching back to unzip her skirt by doing it myself. I love undressing my dates. It's better than Christmas.

She steadied herself with hands on my shoulders as I eased her skirt over her hips and to her feet. She stepped out of it and I carefully put it aside on the chair where I'd placed her blouse.

"You take good care of my things. Thank you."

I smiled at her again. "I really want to see you in them again, Lori. You look so sexy in that outfit."

She murmured, "Thank you, lover. I'll wear them again for you some time. I hope soon!"

She straightened up and I crawled right up to her and began kissing the lovely bulge in front of me. Kisses became nibbles with my lips. I saw the wet spot at the tip of her cock and I had to taste it. I first tasted her panties. She has a lovely, mildly musky taste. That wasn't enough, though, I peeled her panties down and helped her step out of them.

She was now left in just her black thigh high stockings and black heels. I thought that was so sexy I left these things on as I took my first taste of her juice from the tip of her circumcised cock. She caressed my hair and touched both sides of my face. I began a gentle BJ, taking the head of her cock directly into my mouth and sucking on it. I noticed her balls were unusually small, but I was sure that was due to her hormonal treatments. I was happy her cock was still of a good size. If I didn't like femininity so much, I could very easily be totally gay. I love sucking cocks. Trans girls like Lori are the perfect combination of both to me. In her case, adding intelligence and a sense of humor just made the package irresistible.

She seemed to weaken at her knees and I hurried to help her sit back on the couch, me between her thighs. I took my time, giving her the best BJ of which I was capable. I truly enjoyed giving her as much oral pleasure as I could.

Her breathing was accelerating and she was quivering as I sucked her deliciously. I knew I'd hit the point of no return when I felt her cock spasm in my mouth, shooting her seed into me. I swallowed as fast as I could, but I still felt a little dribble onto my chin. With a finger, I wiped it up and offered it to her.

She grinned at me and sucked my finger dry. She then looked down and saw my own hardness. "Oh, my, you seem to have a swelling down there. May I kiss it and make it better?"

"For a bit, but I really want to fuck you. May I put my hard cock into you and fuck you, my dearest?"

She chuckled. "Of course, darling. I want you to fuck me. How do you want me? Doggy style? Missionary? Something else?"

"I want to see your lovely face as I fuck you for the first time, dearest. Missionary it is."

I stood up and took her hand, leading her to the bed where we kissed again, holding each other gently. My hard cock was rubbing against her lower tummy area and she made a point of squirming against me again to excite my member. I was now the breathless one as she backed to the bed, pulling me on top of her.

To my surprise, her cock was getting hard again. So soon! I was ready now, though, and I got the lube and a condom from the bedside table. "Help me put this on?"

She smiled warmly at me. "Thank you, darling. Yes, I will."

She pushed me up onto my knees, and rained a hundred kisses on my cock, almost bringing me to orgasm. Squeezing the base, she grinned evilly at me. "I want you to cum inside me, darling."

When I'd calmed a little, she put just a little lube into the tip of the condom and then expertly rolled it onto my cock, giving the head a little kiss just before she did.

I took the lube and got down between her thighs again, kissing her cock along the way.

"You're so naughty."

"Yes, love. I'm very naughty. I'm about to butt fuck you as good as I know how."

She moaned and I applied a liberal amount of lube to her anus and then put one, then two fingers, then three inside her, lubing her liberally. I finally got down onto her, kissing her lips as I slowly worked my cock into her.

She definitely enjoyed what I was doing. So did I, for that matter. I hadn't had such a good fuck for months. It was amazing while it lasted and it didn't last nearly long enough. I shot my load into her with a growl and a moan. Her legs were wrapped about my waist and she seemed to be pulling me into her as deeply as she could.

I finally collapsed on top of her, enjoying my after shocks. We held each other gently and kissed and caressed each other's hair.

She had definitely grown another lovely erection as we were making love. "You've grown something hard again, my love. What would you like to do?"

She seemed shy, almost reluctant. I found this charming after the sex we'd already enjoyed together. "Bill, would you let me fuck you, too? You don't have to if you don't like it..."

I looked at our lube and condom supply judiciously. "Well, I think we have enough supplies. I mean, if it means that much to you..."

She spanked me playfully. "You beast, you just thoroughly and beautifully fucked me. I'd love to give that back to you."

I kissed her thoroughly. "How do you want me?..."

"On your hands and knees, darling. Stick that beautiful ass in the air for me?"

She knelt beside me and, taking her sweet time, began to caress my cock and ass. She took a glob of lube on her finger and rubbed it all around my anus just before she put more into me. She definitely knew what she was doing. She gently expanded my ass as she fingered me.

Her fingers, brushing along my prostate felt amazing and I became quite hard with her ministrations. "Put it in me, lover. Please fuck me."

She laid down beside me and kissed me. "You want me to fuck you, my love? You want my very hard cock deep in your ass?"

"Omigod, yes, please, please, please! You're driving me crazy!"

She chuckled and kissed my cheek, my neck and then she got behind me. Holding my ass cheeks apart, she gradually and lovingly put the head of her cock into my back tunnel, a little at a time, pulling back to do it again and again, a little deeper each time.

She laid down onto my back for a moment, hugging me and kissing me. "I love this, my dear man. I'm so glad you like your girl to peg you."

The feeling of her hard cock inside me was magical. I just moaned with each thrust she gave me and that seemed to spur her on. In very little time, I felt her cock expand inside me and she began to thrust faster. I could feel her twitching with her orgasm as she shot into me until she collapsed onto my back. I held her up for a moment and then I collapsed to the bed myself, trying hard to keep her inside me.

In a few moments, her cock shriveled to the point it wouldn't stay inside me and I kissed her as I got up and went to the bathroom to start the shower.

"Do you have what you need, darling? The meeting starts at 8:00."

"I'll have to go to my room to change, love. All of my makeup is there, too."

She smiled and just hugged me. I turned so our cocks would just be pressed together. These soft cocks that had just each invaded our new lovers. I love the soft, gentle moments after we've worn ourselves out making love and the lust is sated for a while. Being able to just touch and caress for the sake of a new relationship is heavenly. We kissed for a moment and she said, "I have to get a little sleep. I'm going to have to redo my makeup and change to a different outfit. Is that okay with you?"

I gently held her head and kissed her lips. "Dearest, I'll see you at the meeting. You know we have a long lunch tomorrow. Would you like to come up here again for some more fun?"

"As long as it doesn't make trouble with the bosses, I'll be here and all yours."

We kissed in the shower and I sent her to her room with her clothes in the plastic bag they give for laundry, wearing my bathrobe. I was definitely looking forward to our next day and night together. I wanted to learn more about this amazing woman I had just fucked.