A Downtown MomentbySheermistress©
I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the company.
While I never went out with Loretta, we did have the odd 'encounter' over the year, both of us being single and enjoying experiencing a new city. For what it was worth, there never really seemed a need for the two of us to hook up in a relationship, we both really liked the fact that we were there for each other when the moment came up. Sure, we had had sex and had some fun times 'in costume' or cross-dressing in lingerie etc., but otherwise we were just good friends. Loretta, is not what I would call strikingly beautiful but she has a natural beauty and air about her that is really very sexy; she's relatively tall – maybe 5' 8", gorgeous legs (and yes, I've certainly commented on them more than once!). She has a very athletic figure, and nicely curved along with it. Not overly large breasts but nicely proportioned. She has a presence about herself that she knows she's not totally beautiful but that she has something that a lot of people want – charisma and sex appeal by the truckload! She also knows how to dress, always impeccable and a body that suits office attire naturally – fitted skirts (either long or short), nicely pressed blouses, always in heels – but not overly high, she made a comment once that she was conscious of her height if she wore heels that were too tall. I told her to go with it; she certainly could carry it off when she did.
When I dropped in, it was close to finishing-up time so we chatted amiably about life and what we were doing etc., etc. Being single still, I was happy to hear that she was only dabbling in a relationship at the moment, and not really sure where it would go. As we chatted I couldn't keep my eyes off Loretta's legs. This day was a very good day for me with regards her outfit – she looked the epitome of every crossdressers' fantasy! Her skirt was very well fitted to just below the knee with a slit all the way up the front – it was fine while she stood still, but when she walked or sat down and crossed those long legs of hers, I was greeted by a gorgeous expanse of smooth, tan-coloured pantyhose-encased leg. And today, for whatever reason, she had on control-top pantyhose with the pantie edge being visible through that sexy slit in her skirt, the edge-band embroidered into a very sexy tan-on-tan lace pattern.
She noticed me looking and smiled as she re-arranged her legs making sure I got a very decent look at both legs as she uncrossed and crossed them again.
"So, are you still dressing these days?" Loretta knew about my femme side – we'd been out for dinner one nite, which led onto some bar-hopping into the wee hours of the morning – and after a few drinks Loretta was looking at me and she said, "You have really nice eyebrows for a guy, and your nails, they are so well manicured too."
I took the plunge and told her about my femme self, Georgia. "NO WAY!" she exclaimed...and then proceeded to ask a million and one questions as to how, why, how long and so forth – pretty much what most girls ask when I tell them actually.
Once Loretta knew, we spent many coffee breaks talking about brands of pantyhose, lingerie, clothes, shoes etc. In a way, she became just another 'girlfriend' to Georgia. On the odd occasion that we had some fun together she did ask me to stay dressed – she always seemed extra turned on rather than when I wasn't dressed. Anyway, her question came out of the blue this time and caught me by surprise a bit and I just said,
"Yes, as a matter of fact I still dress. But mostly at home and under my male-drab, there haven't been too many opportunities to get out and about lately."
Then she leaned forward with a naughty smile and asked, "So, what are you wearing today...Georgia?" I must have blushed because she chuckled and added, "You don't need to be shy around me, you know that!" I did know that, but her office door was open and I was a little worried others may have heard her. I looked around and realised that everyone was actually gone for the day. "Everyone seems to take off early around here," she said. "The cleaners won't be in for at least another hour or so, it's actually nice and quiet and I seem to get more work done in these last hours than most of the day. So...tell me," she said again, "what are you wearing?"
So I told her, "well today's a kind of a light bondage day for me," I said. "I have on black, maximum control-top pantyhose with a long-line leg built into them, so 'everything' is tucked neatly in place, a black, lycra camisole with stretch-lace straps and lace edging and lastly, a black waist cincher."
She smiled and said, "Now that sounds very sexy. Want to know what I have on?" I knew she had on control-top pantyhose as I could see the pantie edge sewn into them, so I mentioned them and Loretta said, "Not only are they long-line but it's a full bodystocking as well." Now, I really wanted to see the rest of it! But she went on, "It is really nice and tight all over, the breast area has a lightly structured bra built into it and the stomach and waist are held very tight by constricting panels sewn into the fabric – but the best bit," she added, "is that they are crotchless! I'm wearing sexy black-lace, boy-leg panties just for some added comfort. You really should get yourself one of these," she said, "they only came out recently and they are just the best to keep the figure all tucked in and the curves in the right places. It all feels quite sexy actually." And," she went on, "by the look on your face I bet you'd like to see it too wouldn't you?"
"Of course I want to see it!" I offered, "But not only that, I might just head out after this and pick one up myself!"
Loretta then sat back, smiled and said, "So there's the tell-and-tell, why don't you show me what you're wearing then?"
"What?? Here?!?" I blubbered. "What if the cleaners turn up early, or someone comes back to get something?" I offered. Secretly though, the idea of the two of us in our lingerie in her office had trickled down to between my legs and I could feel my girliecock starting to twitch a little in its sexy confines.
"Trust me Georgia, the blinds are closed and we can simply lock the door. If you're real quiet they won't even know we're in here. And if the door is locked the cleaners leave it alone as they don't have keys to individual offices anyway," she added. She got up and locked the door, came back and sat down behind her desk. Through our little fun times together, Loretta knew my fetish for light domination. She knows that I would love nothing more than to have a strong woman treat me as her prissy girlfriend.
Looking directly at me she smirked and said, "Now, Ma'am has had a very busy day, and she needs some light relief, so why don't you be a good girl and entertain me Georgia. I know you want to, and I also know that you would like nothing more than to see what my new bodystocking looks like wouldn't you?"
I nodded and offered, "You know me too well Ma'am. I would love to see it, may I please?" I asked, thinking she would offer to disrobe first.
"Uh-huuh...not so fast missy! You think I'm going to just undress here in front of you just because you ask? You really need to mind your manners young girl!" she added. I was starting to see where this was going and thanked my lucky stars that I decided to drop in on her today! "Now sissy," she demanded, "come around here and stand before me." I did as told and stood directly in front of her. "Start real slow and don't lose eye contact with me," she ordered, "I want to know that you are showcasing yourself just for me okay?"
"Yes Ma'am", I answered softly.
"Good girl," she said, "now start."
Keeping my eyes firmly on hers and enjoying her wicked smile, I slowly but surely removed my shoes first – her eyes noticing the sheerness of my pantyhose (as I love to go without socks on days when I dress like this) – my jacket went next, followed by my trousers and shirt. Once fully undressed I felt a little 'incomplete' without heels and mentioned this to her. Loretta got up and opened her side cabinet and took out a pair of heels she keeps for wearing around the office – they were a low-heeled, slip-on in plain black with a simple wide band across the foot – somewhat simple, but suited my attire nicely. While her feet are smaller than mine, they fitted well enough being a simple slip-on.
"There my girl, now you're fully dressed as a sissy should be," she stated. Leaning forward she started to run her hands over my nylon-encased legs, "Mmmmm, these are nice – they feel so soft but have a really nice sheen to them," she commented. "What did you say the brand was?" she asked. I told her and she commented that she would have to get some. "Now turn slowly for me so I can get a good look at you," she asked. As I turned her hands played all over my pantyhose, I could feel her nails running across the taut material covering my butt, and her hands slipping between my legs to tease me as I turned.
She spent a little more time examining my waist-cincher and the feel of my cami when she had me stop and, leaning back, she parted her legs, letting her tight skirt slide up her silky thighs revealing her pantyhose-covered legs in all their glory. "You know Georgia, there are times when I think we should just cut all this bullshit and just move in together," she said. My heart skipped a beat and I couldn't take my eyes off her. "You have everything I need in a man – or woman for that matter," she added. "Our little get-togethers always leave me wanting something more each time. And I love the fact that I can play at being a lesbian while I'm with you, it's so much more exciting! And, every time we do get together, it sticks in mind more and more – leaving me with some really naughty and delicious daydreams," she added. I couldn't believe what I was hearing! It would be so wonderful to have someone like her in my life. If only she knew how much I fantasized about being with her, dressed and being treated like the girl and woman that I wanted so much to be. I looked down at her while her hands kept sliding over my sheer legs, every now and then slipping up between them to tickle my hardening (and probably very wet by now!) girliecock.
"Loretta, you're offering and saying a hell of a lot right now. And, I really hope you're not just teasing me - do you really think that?" I asked. "This would be taking our relationship to a level that we never expected it to go," I added, "And besides, what about this guy you're kinda seeing at the moment?" I asked.
"Oh him...naaaah, I really don't think that is going to work. He's just someone I had some fun with but I don't see a future there," she said.
With a somewhat buoyed excitement I knelt down closely between her legs, my hands sliding slowly along them, inching her skirt higher – her black lace panties now very visible and looking very sexy, framing her gorgeous pussy. I leaned in close, reveling in that feel of pantyhose against pantyhose. "You know how much I like to dress, and for that matter, want to dress as often as I can," I offered. "Are you prepared to be a part of that?" I asked.
"As a matter of fact, I've given this more thought than just now," she said. "I've thought about this for some weeks and when you called to say you might drop in, I was beside myself. Why do you think I'm wearing what I am today? And the fact that you are dressed as you are is such an added bonus! I mean, I knew you'd be wearing pantyhose, I guess I got lucky with the rest that you're wearing."
I smiled and leaning forward, kissed her very hard on her sexy red lips. Her tongue pushed between my lips and hungrily searched and probed, turning me on even more. Loretta wrapped her legs up around my back and pulled me to her, "God I want you to fuck me so badly right now!!" she gasped. I leant back a little as her fingers found my hardening nipples and pinched them, making me jerk and hump hard up against her.
"I want that so much too," I answered. "But there's something else I want first," I added. "Get undressed and show me that bodystocking you're hiding! Or you won't get anything from me at all!" I ordered.
"You can see it my girl, but only if you undress me yourself," she said. I didn't need to be told and asked her to stand. Standing myself, I took off her jacket – very slowly I undid the buttons of her blouse, all the time staring directly into her eyes. Sliding her blouse off revealed a very sexy bodice across the top of her bodystocking; I let my hands wander across the sheer material, slowing enough to lightly pinch her nipples. Loretta gasped as I dropped her blouse and reached around to unzip her skirt.
"I really do like this skirt you have on. Maybe I could borrow it sometime," I added.
Loretta just smiled and dutifully lifted each leg as I helped her out of it. We stood there in front of each other, not saying a word, just letting our eyes and hands wander across our bodies, taking in the feel and sight of what we were wearing and, I'm sure, both thinking how nice these outfits would feel on ourselves. Pulling her to me, I let my hands slip down between our bodies and I could feel Loretta's wetness seeping through her sheer panties. Slipping my fingers in a little way, I found her glistening clit and rubbing it slightly I pulled her to me hard and as she jerked and gasped, I whispered in her ear, "Is this what you want Ma'am? Would you like a prissy girlfriend to be there for you? To be your little pantyhose-slut, and service you whenever you need to cum or feel sexy? Do you want me to tease you and please you Ma'am? Do you want to treat me as your sissy-slut, keep you happy and content with my big girliecock? Watch me play with myself while I'm all dressed and girly for you? Hmmmm...do you want all that and more Ma'am?!?" I asked again and again.
It was all Loretta could do to stand, her knees were buckling and her gasps were getting louder as my finger continued to rub and pinch at her very wet clit. "OH GOD! Y-YES GEORGIA!!" she yelled, "I w-want all that and m-m-more!" she added breathlessly. I could tell she was close to cumming but I didn't want it to end there.
I decided to take the bull by the horns and ordered, "Lean over your desk bitch! You want me to fuck you huh? You want to feel my big girliecock all the way inside you Ma'am?!? Then bend over you whore, I need some hot and wet pussy wrapped around my girliecock!!"
Loretta didn't need to be told twice, she smiled a very naughty and devilish smile and slowly but surely bent over her desk and parted those sexy legs wide. Not even bothering to take off her panties, I pressed into her and started to dry-hump her harder and harder.
"Does that feel good Ma'am? Feel my pantyhose rubbing against yours? That's what it feels like when two girls get together –all sexy and sheer. But you want some girliecock don't you? You want me to fuck you and fuck you hard right?"
"Yes Georgia! Fuck me. FUCK ME YOU LITTLE SLUT!!" she yelled.
(God I hope the cleaners aren't here yet I thought!)
I tore a hole in the front of my pantyhose and pulled my throbbing girliecock through it. I Pressed in close against her and let it slide up between her legs. Loretta felt it immediately and reached down to try and slip it inside herself. "Don't touch me!" I whispered hoarsely. "You'll get it soon enough and besides, for now, I'm the one in control – don't even think that you are ordering me around you whore!" I could tell Loretta was getting off on this as she kept pressing and rolling her hips and butt around pushing against me wanting it so much. I pulled her panties to the side, leant forward and pressed myself into her in one smooth motion – she was so wet, her pussy offered no resistance whatsoever.
"MMMMMM!" she moaned, "Ohhhhmmmmm, that feels sooo good Georgia!"
I pressed in hard and then slowly started to slide in and out. Her cunt was so hot and wet; fucking her was just smooth and sexy. I positioned myself comfortably and leant forward to rest against her feeling that sexy bodystocking against my own lingerie. I reached around with one hand and started to pinch her nipples.
I had found that Loretta got so turned on by just having her nipples pinched and massaged. We were both alike in that fact – one night we were lying together in pantyhose and heels and while pinching each other's nipples we made each other cum just by doing that.
"Georgia," whispered Loretta, "fuck me! FUCK ME HARD PLEEEASE?!!?"
I grabbed her waist and started humping and fucking her as hard as I could. Loretta loved being jammed tight; it was one thing that really got her off fast – a good solid, hard fuck. I rammed myself into her over and over as her body started to jerk and spasm, her orgasm building higher and higher. She was so wet by now that her girliejuices were seeping all over our pantyhose – I could feel her wetness running down her thighs and down my own. God I hope she cums soon I thought, I want her to suck me off tonite – I was in the mood for a good girliecock-sucking. Pretty soon I could feel her reach a point of no return.
Not worrying about who was around, Loretta just screamed, "FUCK ME! FUCK ME YOU WHORE!! JAM THAT THING IN BITCH!! GIVE IT TO ME – C'MON SISSY! CALL YOURSELF A WOMAN?!!? SHOW ME HOW A REAL SLUT CAN FUCK, YOU PANTYHOSE-LOVING, COCK-SUCKING LITTLE WHORE!!! FUCK MEEE!! HARDER! OH F-FUCK YEAH! YESS!! I'M CUMMING GEORGIA! HURRY...JAM IT ALL THE WAY IN...OH GOD! AAARRGGGNNNNHUUH!!!
Loretta jerked and heaved against me, trying to push back and wanting to get as much of me in as possible – I really didn't have any more to give to be honest – I was in as far as I could go! Her orgasm washed over her again and again as she bucked and writhed with me deep inside. I held her tight and whispered a whole bunch of naughty and sexy stuff to her as she came down off her roller-coaster ride. The inside of her thighs and all over the front of me was completely soaked by her girliejuices. I stayed inside her for a short while and then slowly pulled out – to which she offered a little moan of regret – and kneeling down, I turned her around and got her to sit up against the edge of her desk, keeping her legs as wide apart. I leant in and lovingly started to lick as much of her girliejuice from her that I could. My tongue kept darting against her wet cunt and throbbing clit causing her to jerk and protest that it was too sensitive but I knew she loved that and kept it up until I could feel another little short orgasm building. She grabbed my head and pressed it hard into her moist mound and cunt, holding me tight with my tongue licking at her slick opening, while she dribbled another juicy orgasm between her legs, and all over my mouth.
"Fuck me!....see Georgia," she gasped, "This is exactly what I need, a 'woman' who knows how to suck pussy – and, with that 'something extra'! You do it just the way a woman wants it – well this woman at least – it's almost as though you know the correct way intimately," she added.
I looked up, licking my lips, "don't forget, I am all woman in my mind. That's the way I think and feel. It's only the outside that shows a man now and then. When it comes to sex, all I see are women – what a woman wants, how she wants it and how it must feel –and I how I would want it if I was being treated like a woman. So naturally I try to be a total woman when I'm making love. The fact that I can fuck you nice and hard with a sexy girliecock is an added bonus."
Loretta smiled and, looking down she offered, "Well my dear little sissy, I think it's time we made you feel like a total slut too don't you think?"