Important Business Comes Up Ch. 02

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Emmcee20
Emmcee20
168 Followers

The knickers were on the bed but Jody said to Sarah, "I want to fuck him. You blew him. I need that cock now."

I was amazed because I wasn't even involved in the conversation, not that I would have said no.

Sarah smiled and gave Jody a deep kiss and then said, "You can have my little brother but don't mess up his make up."

As it turned out that wasn't likely. "I won't," she replied, "because I want him to do me doggy style, just like you do."

The image started to appear in my mind of Sarah with a strap-on dildo. Ummm. Jody then turned to me with, "Just don't work up too much of a sweat and you'll be fine."

I suppose, technically, I was about to lose my virginity. I'd been wanked by my sisters years ago and fondled by, and had fondled and fingered, numerous girlfriends but I was actually about to stick my cock into a woman's pussy! Wow! Jody stood up just in front of me, slipped her top off and tossed it away. Next came down her jeans and under them was a soaking wet pair of silk undies that outlined the shape of her protruding cunt lips. It was like a rushed strip tease but very effective in keeping my attention while at attention. The soft silver lacy boy-briefs with the big wet spot at their centre came off too and there was a shaven cunt that was juice slickened. She slipped out of her flimsy lace bra that I couldn't believe held her gorgeous globes and her huge tits sat there, firm, round and aching for attention to her nipples that were sticking straight out half an inch and she sat down beside me on the bed. I'd never seen nipples like them. At last I was seeing her naked. Stunning! Her flawless smooth skin undulated around every nook and cranny of her slim body. My sister has great taste! Jody leaned back and turned over in the middle of the bed. She raised her knees up to push her butt in the air and, looking back over her shoulder, she said, "Do me hard and fast. Fuck me."

I can take a hint so I climbed up on the bed, knelt between her spread legs and looked at her gaping wet hole as I aimed and then leaned forward and slipped my rock hard cock straight into her soaking pussy right to the hilt. She let out a groan of pleasure as I filled her. The first thing I noticed was how tight her cunt was gripping and flexing on my cock, gripping along my length. The second thing I noticed was how great it felt rubbing my stocking clad legs against her legs as I thrust in and out and how my now neatly trimmed pubic hair brushed against her magnificent tight butt.

I held onto her hips and pounded in and out of her for several minutes before I reached forward to return the favour of attention to her nipples while she thrust back against my every inward stroke. Her magnificent globes filled my hands with warm tit flesh as I kneaded them and tugged on her pointed nubs. I felt the building tension in my gut as my solid girth impaled this beautiful woman. I did my best to maintain a steady rhythm and contact yet I managed to slip out a couple of times as her gripping sheath clawed at my foreskin as I withdrew to allow the maximum inward stroke. Having to insert my cock again was not difficult as her cunt was drooling juice. Shortly Jody lifted her head and she started to moan and then some of the foulest language my young ears had ever heard came from the lips of this woman, "Ungh FUCK! Shove that meat in me Jace! God that cock feels good; fill my cunt. Come on bitch fuck me! Harder! More!! Faster!!"

It was then that I saw why she was so hot. As we were thrusting in and out together on the bed, across the room, sitting at the dresser with her legs spread wide over the arms of the chair, was Sarah leisurely stroking a thick dildo into her shaved cunt, the pink folds glistening and stretching and gripping the dildo as she thrust it in and out of her body in time with our fucking, and just behind her was the mirror. Jody and I filled the large mirror with the image of a woman all made up and wearing a bra and stockings fucking the daylights out of this gorgeous big-titted woman doggy style, her massive boobs swaying beneath her body as she pushed up on all fours and rocked back hard against my thrusts.

That image and the sweet swishing sound of my stockings as I moved in and out of Jody's hot wet nest was just too much for me and I exploded deep inside her, jamming and slamming my cock into her as far as it would go.

She yelled, "Keep going! More!" as she thrust harder back at me and I managed a few more energetic thrusts and her own guttural orgasm made her clamp down on my embedded cock in a vice-like grip as she exhaled an extended, "Aaarrrgh" before collapsing beneath me.

We slumped to the bed panting in unison and rolled so that we lay side by side, my softening cock still nestled between Jody's thighs. We watched while Sarah caught us up in the orgasmic race. She jammed the dildo deep into herself and bit hard on her lip. It was a visible orgasm as she shuddered and moaned; her eyes, that had been fixed on us, glazed over and rolled back into her head. All her muscles seemed to tighten at once and then her deep long groan increased in volume as it reached across to the bed and then she slowed the gyration of the plastic playmate she had left barely visible. Eventually she withdrew it, her glistening folds trying to suck it back in as they gaped open, feeling its absence. She stood up and sauntered around the bed where she lay down behind me to make me the meat in a sexy post coital sandwich. Sarah joined us in a relaxing, caressing cuddle and recovery.

Some while later, I'm not sure how long, the world had righted itself and Sarah touched up my make up and then they dressed me. Jody held my panties as I stepped into them and she drew them up my legs. Caressing the sheer nylons with the satin fabric sent rockets through my senses. Carefully my softened penis was pushed well back so that the look in the mirror showed a nice flat pussy line at the top of my thighs beneath the suspenders. Next came the attractive navy blue ¾ length dress they'd got for me and it felt wonderful as its texture caressed every part of my body that wasn't already in raptures from the matching lingerie. It's open neck and split sides gave me every opportunity to twirl and turn and catch glimpses of my sexy self in lingerie in the mirror and feel its presence as its skirt glided across my stockings. I was already in heaven. Lastly it was the shoes with medium heels, as they didn't want me to have trouble moving about. I took a few moments to gain balance and some poise so that I could stand straight. There I was for the first time in all my glory. I'd never gone the whole way with make up, lingerie and clothes all at once, but boy was I impressed with what I saw in the mirror. I stood admiring the look and the feel while, in a matter of minutes, the girls were dressed to kill and that's when they told me we were going out. I panicked!

"You can't be serious! This has been great fun but you said I could stop if I thought it was too weird. Well I've never been anywhere like this. In fact this is the first time I've done all this. I'm not sure I even know where we could go that I wouldn't meet some of my friends."

"It's okay," Sarah tried to assure me. "We've been planning this a while; don't worry. First we're going to a club way over the other side of town and secondly, have another look in the mirror. Do you really think you look like you?"

Jody added, "We've loved this too and don't want to spoil it but aren't you a little curious about whether you would pass the real test? Being seen by others who don't know you are definitely a man ... and I've felt the proof!" she smiled.

They had a point. I looked like all those 17 or 18 year olds at our school ball who looked 25 all dolled up in their gorgeous gowns, make-up and hair do. Maybe they were right. Could I really think of any of my friends who would be going out to clubs, especially on the other side of town? Eventually they convinced me to try and promised to take me well away from anyone I might know. So long as we went somewhere far away that would be okay I guessed but surely I'd be spotted before I even got in. Wouldn't they just throw us out? As they saw the idea starting to agree with me, they started walking me out of the house. The fast paced chat kept going -- they completed my identity as I already had a name, Jessie. I now had a job in an office as a receptionist and had only moved here recently from interstate and was staying with my cousin Jody. A simple cover story in case we got chatting with someone. Really it was so that I didn't notice that we were already in the car by the time they stopped their excited chatter.

We drove for quite a while and my nerves kept jangling in my brain, "What are you doing?" Finally we arrived at some club and the girls linked arms with me so my unsteady gait could be supported and drew me inside before I had a chance to change my mind. We brushed past the doorman who looked us all up and down. For the first time I thought that I might just pass this test but how feminine did I appear and act up close. It was not like my sisters had ever trained me although I had studied them and many other women in my life, the way they moved and gestures women made. The club was dimly lit with soft warm lights over the booths surrounding a central dance floor and music was pumping from some hidden source over by the long bar that lined one side of the room. We quickly found a table. I was in a panic but they assured me that no one would ever suspect a thing.

After chatting for a while, and a couple of drinks, Sarah said, "Come on Jessie, it's your turn to buy the next round. Three more Cowboys. Off you go."

She pressed a twenty dollar note into my hand and pushed me towards the edge of the seat. I had to go and confront the barman and to get there I had to cross the floor alone in these new heels. Nerves jangled and I started to resist but the look in both the girls' eyes made it clear I wouldn't get away with it. I stood up and suddenly it felt like everyone was watching me. I took my first tentative steps and while unsteady, I appreciated that the girls had thought to get me these low heels, as much as I liked the idea of some four-inch pumps but maybe later. I skirted the edge of the dance floor where the crowd was dancing and finally made it to the bar without falling in a heap. Now to see if I could pass as a girl in the voice department. I'd not had to speak to anyone except the girls so far and they knew I was a guy. How did a girl sound? I decided to try a slightly higher pitch and see if I could keep it there.

"Three Cowboys please." I said to myself -- not too bad I guess but I would soon know. The barman arrived. He was about 25 and had that good-looking movies barman look about him.

"Yes honey, what can I get you?"

Was he being funny or did he really think I was a honey? "Three Cowboys please," I said in my attempt at a female voice as I handed over the money.

He took the cash, stroking my fingers with his as he clasped the note, all the while riveting me with his blue eyes. "Sure. Where are you sitting? I'll bring them over."

I smiled. He really did think I was a girl. I turned and gestured to our booth and Jody and Sarah were staring straight at me with big grins. They were enjoying the show. I turned back to the barman.

"Over there with my two girlfriends. Thanks." I smiled at him and turned to walk back. I made a bee-line for the booth and the girls were in fits of giggles when I got there.

"He didn't take his eyes off you until you were half way back," Jody declared. "You made a real impression there sweety."

A moment later and there he was at the table standing tall over the three of us. He took in Sarah and Jody with obviously appreciative looks up and down before turning to me.

"Here you go ma'am. Enjoy your drinks and if there is anything else I can do for you just let me know." He smiled broadly at me as he nonchalantly placed the drinks and my change on the table. He only had eyes for me at this stage and then he turned and returned to the bar. I was stunned; he really thought I was a girl.

"He's yours if you want him Jessie," Sarah laughed.

"Don't tease her Sare. That's not nice. You can see she's still in shock thinking about what size cock he has," she laughed.

That brought me out of my reverie. "No ... no that's not what ... I mean it's just ... ohh!"

"It's okay Jessie. We understand and we're just teasing. You really didn't think you'd be able to get away with it did you?" Sarah questioned. "But look; he has hardly taken his eyes off you since he got back behind the bar and I wouldn't mind betting he's got a bar behind the bar just for you."

Again the girls laughed but I turned to look and sure enough there he was looking straight in my direction and when he caught my eye, he smiled and nodded. I didn't know what to do so I smiled back and turned back to the girls. We quickly downed the drinks and then the girls said, "Come on Jessie, let's dance."

Next thing I knew I was on my feet and unsteadily guided to the dance floor. The music was loud and fast and the girls kept me close as we moved to the music. I felt very conscious of the crowd around me but the effect of the drinks and the giggly laughter of Sarah and Jody made it all seem fun. Soon I was dancing with them and getting into the atmosphere of the club as well as gaining some control over my feet in heels. This was a place to have fun and the sensations streaming through my body as the dance moves caused the rustle of fabric on lingerie, and the caressing guidance of the girls' dancing, made this an incredibly enjoyable experience as again several people looked our way.

We went back to our table and there was a serve of drinks waiting and an upturned drinks coaster with some writing was sitting next to the glass where I had been sitting. It read 'This round is on me. Give me a call.' It was signed Greg xx and a phone number. The girls were in fits but I picked it up to show that I was reading it and turned to see Greg was watching; I smiled and nodded again and tucked the note down my dress front inside my bra. He grinned broadly and I turned back to the girls. We all raised our glasses to him and downed them in one; he laughed and took a little bow.

I suggested, "I think we had better leave before he gets too carried away. But I need to pee."

"Well that's okay because we do too. We girls always go to the loo together," Jody responded in a girlish voice.

We were up and moving again before I knew it and headed towards the toilets in the far corner. As we neared them I glanced up and without thinking started towards the men's but Sarah grabbed my arm and announced loudly to all who were nearby, "Where do you think you are going sweety? Into the men's again to see who you can pick up?"

There were a few chuckles at the comment but my embarrassment was soon to deepen as we entered the Ladies' to find a few women doing their make-up in the mirrors that were opposite the stalls which all had their 'engaged' signs showing. Their chatter briefly halted as they looked the three of us up and down in the mirror before continuing their discussion about some guy who hadn't called and now wanted to come around for a fuck. As that continued, two adjacent stalls opened and two women walked out and over to the sinks. We waited but the girl whose boyfriend was apparently an "egotistical conceited arsehole" interrupted her tirade and make-up application to say, "You go ahead."

So Sarah and I entered a stall each and closed the doors. I turned to look at the quite clean walls and toilet, nothing like most male loos I'd been in. No graffiti and a tampon disposal unit in the corner. It hadn't occurred to me that the toilets would be so different but then I hadn't spent much time in the Ladies' loo at school or anywhere else. So I lifted the lid and stepped up to the pan; I leaned forward and raised the front of my dress to expose my semi-hard and panty covered dick. As I was fumbling to get it out of my panties I heard a harsh whispered, "Sit! They can see under the door in the mirror!" come from above me.

I looked around and up and there was Sarah looking down at me from over the wall of the stall. Then what she had said dawned on me and I quickly turned around and dropped my knickers and sat down. The semi-hard cock had died the death of embarrassing reality as I looked at the back of the door to see the bottom had a gap of over a foot. In fact the top of the door wasn't that high either and I had probably been seen standing up. Obviously Sarah would have been seen leaning over the top of the cubicle. The jig was up! I realised that the conversation I'd been hearing about, "Well if he thinks he's getting his cock in me tonight ..." had suddenly stopped.

The silence persisted and I was straining to pee but not to pee loudly knowing that all the attention in the whole bathroom was on what was coming. Slowly the piss eased out of the end of my penis and the flush of the toilet in the next cubicle gave me the cover to quickly finish what I had desperately needed to start. I heard Sarah's door open and Jody obviously entered. I couldn't move. How could I go out there knowing that these women all knew I was a guy dressed as a woman? I'd just have to wait until they'd left ... but they hadn't been to the loo yet. This could take ages. The conversation outside had gone; perhaps they had entered the loos. Sarah announced, "Come on Jessie. You're not here for a holiday."

I took that as a sign that the coast was clear so I stood and took some toilet tissue to wipe the last drops from my dick that I would normally just shake off. I dropped that tissue in the loo and lifted my knickers back into place and tucked myself away, making sure not to catch my dress in my panties at the back. I flushed the loo and popped the seat back down and took a deep breath before opening the door. The door opened to reveal the women at the counter still paying attention to their make-up but now in silence. All had their eyes on me as they paused in the activities. Finally the tall mouthy one commented, "Well hello lover. Out for a night with the girls are we?"

The last part of her comment was toned in such a way that they all broke into gales of laughter and Sarah grabbed my arm and led me out. Jody was soon behind us and then Sarah said, "I knew they were never going to leave until they saw you Jessie. Jody, I think Jessie has had enough for one night. Let's take her home and fuck her. What do you think?"

My ears pricked up to the message and my embarrassment soon eased as we headed towards the doors. I caught a fleeting glance of Greg, the barman, trying to catch my eye as we crossed the room and some of my confidence came back. We were soon on our way. Needless to say we spent a lovely long evening together and, over the next few weeks, we repeated the club visit and various other aspects of that first evening, all of which included me being dressed more or less to kill as a woman. And I had fallen in love with it and all the sensations I had experienced!

On our fourth or fifth visit to the club we had been dancing and drinking for a while. By now I was much better on my feet in the heels and the girls were talking about taking me shopping to buy some new clothes and shoes. I was now much more relaxed at being in my girlie attire in public and quite enjoyed the looks I got from the various guys who frequented the club as they looked us three girls over, even though Greg seemed not to be working on those nights we were there. While sitting in our booth these three guys came over and asked us to dance. Sarah and Jody eagerly agreed and dragged me onto the dance floor with them. So far it had been ogling from a distance but now it was up close and personal. I was nervous yet excited at the thought that these boys had no idea what I kept hidden apparently so well. After a couple of songs and dancing as a group we somehow had paired off. I have always loved the cross dressing and all the sensations that it gave me but I had never really had any urge to try sex with a guy but it was also a lot of fun seeing the reaction of these guys who thought I was a girl.

Emmcee20
Emmcee20
168 Followers