My husband and I had quite an open marriage. We were both fairly sexually adventurous and this was reflected in how we both considered it to be ok for us to be going out and sleeping around provided we were completely honest about it and came home and told the other one all about it. In fact, after a while, we found that this recounting of our bedroom exploits with other people became such a turn on in itself that it fuelled even hotter sex between us. We also liked to spice things up by inviting other people into the bedroom with us for threesomes. These were, however, always women. Now, I've always had my slight lesbian tendencies, indeed I've often been of the opinion that the female body is a thing of far greater beauty than the male, many of my own sexual adventures had been with other women, so it wasn't like I didn't enjoy the pleasures of sharing my husband with a hot girl. But still it frustrated me that we could never get another guy involved, my husband was so insecure about his sexuality. This, of course, just made me fantasise even more at the thought of him sucking on a big, fat cock or being taken from behind. I knew that he would love it, every time I told him the stories of the nights I'd spent with other men, how I enjoyed sucking them off, when I described the feel of their cock's sliding inside me, he got such a hardon, I could tell he wanted it. Naturally, when I brought this up, he got even more defensive and masculine and no way would he agree to my suggestion to bring another man into the bedroom. So, I had to content myself with girls.
One night, when my husband was out of town, I went out to a bar where I knew a lot of loose, slutty, often bisexual or just curious women hung out. I sat at the bar and bought myself a drink and turned to check out the talent. One woman in particular caught my eye. There was something about her that looked familiar but I just couldn't place at all where I knew her from. Unlike some of the other women here, who were flaunting there wares, she appeared a little shy and awkward, but this didn't make her any less sexy. In fact, her nervousness seemed to attract a lot of attention from around the bar from both guys and girls. She was tall and skinny with small, round breasts. She had long sandy blonde hair and bright blue eyes concealed behind thick black rimmed glasses, her features were soft and feminine and she wore little make up but some pink lip-gloss. She was dressed in a tight red strapless dress with a short skirt that showed off her bare legs and strappy heeled sandals.
There was something about her that was very familiar, maybe she'd been here before but she looked to have the nerves of someone who doesn't come out to bars alone that often and so I decided to go over to talk to her, to save her from all the men that might seek to prey on a sexy, vulnerable looking girl, and maybe to prey on her myself just a little. It was always the shy looking ones who were won over by a strong woman and turned into real dirty bitches when you got them into bed. Besides, there was that something about her, I was determined to remember what she reminded me of or where I might have seen her before.
"Hi, I haven't seen you in here before?" I said sliding into the stool next to her at the bar.
"No, I'm new," she said quietly in a little girl voice, although she looked at me gratefully with a little smile for keeping off the guys, she was obviously still very nervous.
"Well, a place like this is no place for a nice girl like you to be alone," I said, putting my hand on her arm in a reassuring way, "Let me buy you a drink. What's your name, honey?"
"Er...Cindy," she said after a little pause as if the situation was so new to her that she'd temporarily forgotten even her own name.
I bought her a glass of white wine and we took a booth in the corner, with a little drink inside her she seemed to relax a little and to open up but she was only ever really vague when I asked her questions about herself. Still, we seemed to be getting on fine even though there were a fair few long pauses in the conversation as I stared at her and tried to work out where I knew her from, it was the glasses and her eyes, they were definitely familiar, bright blue eyes behind thick dark frames. Meanwhile, I could clearly see in these pauses, her own eyes running all over me. At first, I wondered whether she might know me from somewhere.
"I'm sorry, have we met before, Cindy?" I asked and she blushed and looked down at her feet for a second.
"I don't think so," she mumbled.
"I was sure you looked familiar."
"Like I said, I'm new,"
She looked up at me and now I felt sure that she was checking me out, maybe not out of recognition, maybe she was thinking about me the same as I was about her, mentally undressing me, wondering what it would be like to taste my pussy, which was, frankly, getting quite wet at the thought. I wondered whether Cindy had ever been with another woman before. Frankly, given how nervous she seemed, I wondered if Cindy had ever had sex with anyone before. Well, tonight could be her lucky night. I slid across the seat until we were side by side and put my hand on her knee and began to caress her bare thigh, exposed by the shortness of the skirt of her mini-dress. I looked into her eyes and smiled as they lit up with a not unpleasant kind of surprise, she was enjoying this. I looked into those sparkling blue eyes and suddenly it struck me.
"Oh God," I gasped, "That's where I know you from."
As soon as I said that, her pale features blushed bright red, she slid away from my hand on her thigh and, with a look of fear in those pretty blue eyes, was about to run from the bar. I grabbed her by the arm and tried to force her back to sitting next to me while at the same time being as gentle as possible, I didn't want to cause a scene. I got her to sit back next to me.
"It's ok, I won't tell anyone," I said trying to reassure her and it seemed to calm her down a little.
What I had remembered in that instant, looking into her eyes was just where I'd seen those glasses before, Cindy was my son's maths teacher. Now, you'd think as an attentive parent, and I'd like to think that I am one, I would have recognised my son's teacher sooner, only, the thing is, my son's maths teacher is a guy, Mr. Lawrence. I remembered meeting him at my son's parent teacher night, he was very young, this was probably his first teaching job, fresh faced and boyish, he looked almost too young to be a teacher. His slight frame made him easily intimidated and he was very nervous around me and my husband. The school was a posh private school and the parents could be quite pushy so he struggled to tell us that our son, although a smart eighteen year old kid with a bright future was a bit of a troublemaker and Mr. Lawrence was having trouble controlling him. I guessed he was well aware that that could get much worse if people knew he lived a double life, crossdressing as Cindy. If I told everyone what I saw tonight then he'd be humiliated at school, that is if the pushy parents even allowed him to stay in a job around their precious children. Fortunately for Mr. Lawrence/Cindy, this wasn't at all what I planned to do.
"Don't worry," I said, sidling around next to him/her once again and leaning close so I was practically whispering in her ear, "This can be our little secret. I'm not about to judge. Actually it kind of turns me on."
I could hear her gasp at this last thing as I tickled her ear with my tongue and ran my hand around across her chest and down to her crotch where I stroked across what was obviously some stirring arousal in "her" cock. I leaned further over and began to kiss her on her lips, she relaxed and let my tongue rub itself across her lips and invade her mouth as I rubbed my hands all over her tight body in its tiny little dress. She let out a little, very convincingly feminine moan as I pulled my lips back from hers, her back was arched and her eyes were closed. She was really into it.
I took her by the hand and we headed for the toilets. Inside the ladies, we found a cubicle. I pushed Cindy down onto the toilet and sat astride her legs, kissing all over her pretty face while he/she fumbled to untie my halter top, Mr. Lawrence obviously wasn't very familiar with women and so Cindy was struggling with it. I pulled out of the kiss and undid the straps, I wasn't wearing a bra beneath so my large round breasts spilled out into her face. She looked wide eyed with amazement and excitement.
"Is this your first time with a woman, Cindy?" I asked.
She just nodded, her mouth open, as I pushed one of my breasts into her pretty pink lips and had her suckle on my nipple. My now there was a severe ache of arousal between my legs and I could feel the white cotton panties I wore were soaking right through. This wasn't helped by feeling Cindy's cock, obviously hard and erect now pressing into me through her dress.
I pulled her dress up around her waist to reveal she was wearing a pair of tiny black lace panties, she had pretty good taste for someone not used to being a girl, they were stretched out and the head of her cock poked above the elastic waistband. I stood back and slid her little panties down around her sandal wearing ankles to expose her whole cock. It was by no means that big or thick but it was certainly enough for me. It was already really hard and throbbing and a couple of drops of shiny pre-cum hung on the end. I pulled my own panties aside, pushed up my short skirt and straddled her once more, lowering my warm, wet pussy onto Cindy's rock hard cock. I began to rock back and forth on her as she quivered with excitement and caressed my breasts. I loved the feeling of a hard cock filling me up, but what was even better was that it was doing it while I was making out with and caressing a beautiful girl, our soft bare legs rubbing against each other. I'd never done it with a shemale or a crossdresser before, but I could tell this wasn't going to be the last time.
I could tell that the stimulation of fucking her first woman while dressed like one was going to be too much for Cindy pretty soon. Her eyes were tight shut as she seemed intent on concentrating on holding back, but she didn't manage for long and soon her body was convulsing and she was filling me up with her hot, thick spunk.
I hadn't managed to cum yet and was still really hot and horny from having Cindy inside me, but her cock was now limply flopping out of my pussy. Oh well, I thought, there's always next time. But, Cindy wasn't going to leave me hanging. Like a true gentleman, even though he was dressed as a lady, he/she got to her knees on the toilet floor and buried her face in my crotch. Her cunt licking wasn't expert but it was certainly eager, although I expect that part of that joy for her was in eating out the cream pie she had left in there as much as going down on a woman. Still, with her tongue all over my pussy lips and clit it didn't take long before I leaned back on the cubicle door moaning and screaming with pleasure as my own orgasm shook through me.
"Fuck Cindy, that's amazing, you're a fucking natural," I cried, oblivious to anyone coming into the toilet who may hear us, "Yes, Yes, YES, FUCK YES"
When the waves of pleasure finally subsided, we both put our panties back on and walked back into the bar for another drink. Certainly, a few of the other customers gave us some funny looks but this wasn't the first time I'd been eaten out by another girl in that cubicle. It was the first time, however, that I'd done it with a girl with a little something extra and, while Cindy's head and been between my legs, bringing me off to a hell of an orgasm with her oral attentions, I had had quite an idea about what this hot girl with the best of both worlds could do for me.
Over another drink, I learnt how David Lawrence had been dressing up as a girl since he was a teenager, always keeping it secret from his family and what few friends he'd had. He was shy around woman and sex and had never had a girlfriend, instead he'd buried himself in his studies and dressing as a girl at home and jerking off to his fantasies. Since starting work as a teacher at my son's school, his feminine wardrobe had expanded greatly and he had become pretty skilled at looking and acting like a girl. Tonight was the night that he had decided to throw caution to the wind and go out dressed as Cindy. He/she said that he didn't exactly feel like he was a girl but he knew that as Cindy he felt much sexier and more comfortable than as David and that he wanted to experiment with the possibilities being Cindy could bring him. He had always liked women, he was pretty sure of that, and so was I given how quickly I was able to bring him off in the toilet cubicle, and had always lusted after them even as he envied them their beautiful outfits. At the same time, a lot of his fantasies involved Cindy being taken by a hot, studly man, although he had never acted on these either, he was quite curious about it. I told him my plan for what I wanted from Cindy and he was happy to oblige after very little persuasion from me.
You may remember how I told you that my husband, Terry, objected to my desire for a threesome with another guy even as he encouraged me to bring home girls for one and even as I could tell how turned on he was by my tales of guys that fucked me. Needless to say, I thought gorgeous, sexy but hung Cindy could be just the one to bring my husband around to sucking cock. For once, I didn't give him all the juicy details of one of my sexual adventures. Instead I told him that I had a surprise for him, that I had met a very special girl in a bar and that I had invited her around to have a bit of fun with the two of us. I could tell that he was already pretty excited by the prospect.
A couple of days later, my son was staying over at a friend's house so we had the place all to ourselves. At a few minutes before we had agreed, Cindy rang the bell of our house and I let her in. My husband's eyes nearly popped out of his head when he saw her, a hot blonde girl in her early twenties. Not only that, but Cindy was dressed up just to my specifications. I had seen Terry staring with ill disguised lust at some of our son's schoolfriends, girls that Cindy taught in her other incarnation as Mr. Lawrence, maths teacher, so I had asked Cindy to come dressed in the school's uniform for girls.
Cindy had really outdone herself with the outfit, a thin white blouse through which her red bra beneath was well visible and which would certainly not have been allowed in the school, unbuttoned to reveal the tiniest amount of the top of her lacy bra, and the school's red and blue tie hung loosely around her neck. Of course, she didn't have any breasts so appeared a little flat chested even in the padded bra, but I knew that Terry liked skinny girls like her above plumper, fuller figured, big breasted types like me. Her pleated skirt in a red and blue plaid design was so short it ended a couple of inches above the knee, again this was surely not allowed by her school rules. Her long, sexy legs were covered by white thigh high nylons which weren't quite a part of the real uniform but made her legs look totally gorgeous, on her feet were a pair of patent leather black pumps. She was still wearing her thick rimmed glasses with dark eyeshadow and scarlet lipstick. Her sandy blonde hair was tied in little pigtails. If she was a schoolgirl she looked more like the school slut than a good girl and yet her glasses, her eyes, her shy, nervous expression implied a certain uncorrupted innocence. When I had told Terry that Cindy was a virgin and had never been with a man he practically creamed his pants right there, a similar reaction to what was going on when he saw her now for the first time. Fortunately, he never paid enough attention at these parent-teacher events to be troubled by the same sense of recognition as I was.
Terry wasn't really one for small talk and frankly that was pretty good for Cindy given how confused she still was over her identity, so we quickly took things up to the bedroom. Terry stood a lot taller than Cindy and had to bend over to kiss her. As he pulled her face to his, I could see a note of fear in Cindy's eyes, this was going to be the first guy she kissed. Terry took complete control, pulling Cindy in and holding her body against his while they locked lips and wrestled tongues. Cindy let out a sigh, which I assumed to mean she enjoyed it, as she was released from my husband's embrace. I turned her round and began to kiss her myself, before directing her lips down my neck to bury her face in my cleavage. As she bent over her skirt rode up to give my husband a good view of her magnificent arse in lacy red panties.
As he watched what he thought to be two beautiful girls kiss, and then Cindy take off my shirt and begin to lick my tits and flick her tongue across my erect nipples, he stripped totally naked and began to jerk off his already semi hard cock.
"Save some for Cindy," I said shaking my head at him.
"Come here then Cindy, and taste a bit of this," he said waving his six inches of meat towards her.
"Here's your chance to fulfil some of those fantasies Cindy," I said, "Just imagine yourself as the cocksucking slutty schoolgirl, desperate to please her teacher."
Cindy grinned and got to her knees in front of my husband. She reached out slightly gingerly to hold his cock and began to stroke it. I knelt beside her and began to circle my tongue around the head of Terry's cock as it grew harder.
"Your turn Cindy," I said and she obliged, moving her lips to kiss my husband's meat.
Still running her hands over it, she began to lick it before opening her lips and letting it inside her mouth. I left her to it and sat back to watch. It was quite an arousing sight, watching this hot crossdresser sucking on her first cock, my husband's, while he, blissfully unaware of her little secret, urged her on.
"God, Cindy, you're quite the cocksucking schoolgirl whore," he groaned as she eagerly bobbed back and forth on his hard cock, "You certainly aren't gonna need any lessons in giving head."
It was impressive to see this formerly nervous little girl quickly transforming herself into an eager cocksucker, doing whatever she could with her lips and hands to stimulate my husband's cock and balls, a little arousing for me too, watching it. I shed my skirt so I was just dressed in some little black satin panties, which I slipped my hand inside and began to rub my cunt with two fingers while Cindy was bringing my husband to a climax in record quick time.
"Fuck Cindy, you're gonna make me cum. You'd better be ready for it," he groaned.
And with that, Cindy managed to give her first man an orgasm. My husband had her by her cute pigtails as he thrust the full length of her cock down her throat and shot his cum inside her. Pretty soon it was leaking out of the sides of her little pink mouth and he pulled out and stroked his cock, spurting more cum across her face, over her glasses, in her hair, onto her chest. As Cindy licked her lips clean and seemed to savour my husband's cum in a way I'd never quite seen in any of the other girls, my fingers moved faster and faster into my cunt until I was moaning and screaming and my body shook all over with the pleasure of my own orgasm.
Cindy and Terry had turned to watch me as I came with just the help of my hand and their sexy show. I grinned at them.
"Well, it looks like Cindy's the only one that's left out here. How would you like to give her the pleasure she gave you Terry?" I said, winking at Cindy.
I walked over and pushed my husband to his knees as Cindy stood up. Once more, I pulled her into a passionate kiss, her hands were all over my breasts and arse, meanwhile mine crept to pull up her skirt. I locked my fingers in the waistband of her pretty scarlet panties and pulled them down around her ankles. I turned her to face where my husband was kneeling and boy did he get an eyeful! With her skirt hanging around her waist, Cindy's cock stuck straight out of her crotch and straight towards my husband's face. It was already partly hard and aroused just from the pleasure of giving in to her slutty side and giving her first blowjob.