Important Business Comes Up Ch. 02

In a very short time the music softened and we were dancing quite close and I was starting to feel a bit turned on by the attention I was receiving. Phil was athletically built and very tall as my 5' 11", and in heels, still meant I only came up to his nose. He had sandy-blonde hair and was a good looking guy, as were his two mates who were all obviously in the same team of some sort, probably basketball given their height. They were all pretty smooth movers both on and off the dance floor and it was quickly obvious that they were all looking for something more than a dance. As I watched the other pairs I could see the moves being made on Sarah and Jody and then I noticed Phil. He moved in very close and started whispering in my ear as his hands moved across my hips, obviously feeling my suspender belt. He caressed my body until his hands found my butt and suspender straps and he massaged my silken covered cheeks, pulling me into his body so that I could feel the lump in his pants against my thigh. All the while his whispers were clearly about one topic! He wanted a blowjob and he really wanted to see my lips stretched around his cock head. Fortunately my own cock was well tucked away because it was straining for release. I couldn't believe what was happening to me because I suddenly found myself nuzzling into his neck and feeling like I wanted to let him know I too wanted to try this -- this was all happening so fast.

He looked down at me and leaned in closely to kiss me gently on the lips, just a small and soft peck on the mouth. It was another first but didn't seem too strange -- I was actually attracted to this guy. We were in the middle of the dance floor and the music went on as everyone around us continued to dance. He took my hand and led me back to our booth where we sat down in the dim light. The others were already way ahead of us and it was clear that the guys had all shared the same idea because Sarah and Jody's hands were busy under the table. Phil took my hand and placed it on the lump in his pants. Now Sarah took the initiative and looked straight at me and said, "Come on Jessie -- we'll do them all together!" The guys' approval was obvious from their comments and that Phil was fumbling with his pants so that he could catch up to the other two at the table.

Suddenly I had a solid cock in my hand. At least I knew what to do with that; I gently squeezed the pliant muscle and felt its pulse as it throbbed in my hand. I stroked it up and down its full length and felt the ooze of pre-cum seep over my fingers. Again the girls took control as Jody said, "On the count of three! One ... Two ... Three!" and their heads disappeared beneath the table.

Phil encouraged me to join them with his hand behind my neck and there it was -- his cock at my lips. In the cramped space and dim light it was hard to tell his size but what protruded from his pants was an inch or so longer than my grip though not as big a handful as my own thick shaft. It was a quick comparison that amused me as Phil still seemed to have no idea that I had such a convenient point of reference just under the table straining to escape my panties. His smell was very like my own and I figured I had tasted my own come on occasion so why not. He pushed gently down and I opened wide.

The soft flesh of his cock head was incredibly smooth to the lips and tongue -- something I hadn't expected. I bobbed my head up and down as I stroked his cock with my nail-polished fingers wrapped around his firm shaft. I swirled my tongue around his helmet and flicked it across the sensitive perineum of his cut cock. I poked the tip of my tongue into the glistening pee hole before engulfing him as deeply as I could, thinking of how Sarah had swallowed my cock on that party night. I guess the situation got the better of him as it took only a few strokes before he started to twitch and a flood of come splashed into my mouth. I did my best to swallow but there was a lot of the salty nectar to take. It oozed over my red lips and onto my chin. I was obviously the last to finish and we were out of there in a flash with giggles and laughter as we wiped our mouths on the way back to the car. We had enjoyed an evening of teasing and titillation and I had my first taste of another man's cum. I can't honestly say whether it was that he thought I was a woman, or that I just enjoyed sucking his cock, that made this such a wonderful experience but I was eager to try again soon. What a night.

It was odd relating all of this to Dana as it wasn't actually getting me all that horny. Don't get me wrong, it was exciting retelling all those sexy moments but at the same time it was like having a girlfriend to talk girlie stuff over with, something I had missed for a long while. Here I was telling some of my most intimate secrets to a woman who was spectacularly attractive and who had sucked my cock only that afternoon, yet I wasn't particularly turned on, just very comfortable and relaxed. We had been sitting together on the couch as I had retold this significant event in my life as a crossdresser. Dana had been a very attentive listener and all those rumours about her seemed so far from right. I guessed that we would soon have the dinner she had invited me for and then discuss the business deal I had brought to the company. How wrong could I have been?

She shuffled towards me on the couch, "That was an amazing story Jason. You really have been dressing as a woman for that long? Just the thought of seeing you that way has me so hot!" She reached behind her back and I heard the ripping zizz of her zip being lowered and she said, "Get out of those pants! I want to see what you are wearing before you fuck my tits."

With that she dropped her shoulders to shake off the top half of her dress to reveal her exquisite creamy breasts and nipples standing at attention. She slowly lay back on the couch, her eyes burning in to me as I rose, mesmerised, and dropped my pants to reveal my maroon satin panties with matching suspenders and sheer stockings. "Now get that cock your sister sucked between my tits and come on my nipples. Make it rough and quick!"

I was hard already and I straddled her body on the couch and pulled my knickers aside to allow my cock to spring forward to the underside of her right tit. The bulbous globe quivered at the contact and I saw the first small smear of pre-cum as it caught the light in the room. She reached out for her glass and poured a small splash into the mountainous valley between her breasts to lubricate her skin. My thick shaft grazed between her globes as she squeezed them around my cock and I moved forward on the couch to thrust my hardness into her warm body, the cool wine providing an aromatic oil to increase the feel of her hot skin against my thighs and loins. She stared straight into my eyes defiantly as I increased the speed of my thrusts into and out of her wonderful cleavage. "Faster! Let me feel your balls slapping on my tits!"

I pulled my panties further across to release my tight balls from their sensual confines and continued to thrust in and out of her boobs being sure to drive hard forward and have them slap the underside of her tits. My cock peeked out the other side of her bountiful breasts as I thrust forward and each time it did, Dana couldn't resist a glance at my pink helmet appearing with the foreskin stretched back between her breasts. After another dozen or so strokes she eased the pressure of the squeezing tits and said, "Jerk off on my tits. I want to see you spurt on my nipples. Nowhere else -- understand!"

The harshness of the final words made defiance impossible. She released her breasts and my hard cock sprung up. Still straddling her body I reached down to grip my cock and commenced long slow strokes of my hardness. I could feel my cum rising and knew it wasn't long before I coated these glorious tits in my feminine paint. "Faster!" Dana demanded, "I don't have all night!"

I increased the pace and soon those familiar throbbing sensations started to rise and my sac tightened. I leaned forward and pointed my cock directly at the right nipple as the first spray of cum splashed on the erect nub. Quickly I swayed to the other side as my second splash nearly made it but fired a broadside at the cleavage side of her left breast and dribbled down her tanned flesh to pool between her tits. The next eruption was a direct hit on her left nipple, coating her areola. I did my best to evenly share the remaining drops of cum to both tits and I stroked it until there was nothing left to deposit and my cock started to wilt. Dana disdainfully announced, "Quite good shooting Jason although one misfire went astray. Rub it in with that soft cock of yours. Let me see you get it hard again."

Spent as I was, she wasn't done yet. I guided my cock to the pointed nubs and used it as a brush to paint my cum all around her areolae. Sure enough some life sprung back to my limp cock to give it a half-hardness. I couldn't believe that I was able to get it up again so quickly. The more I painted her beautiful boobs the firmer I got.

"Umm that's better. Good to see a bit of life still there. Now lick me clean. You said you'd tasted your own cum on occasion; let's make this an occasion. Start with that misfire between my tits. What do you think of my tits Jason? Do you wish your pitiful B cups were as big as my double Ds?"

The last comment stung but I was already moving down her body so that I could dip into that wonderful canyon. "Don't drag that cummy cock over my dress! Now hurry up and clean my beautiful tits."

I stood up to avoid staining her dress and leaned in to lick my cum from between her boobs. I delved in to lick the warm cream that had stuck to the side of her tit. Licking her warm flesh and burrowing my face between her globes to gather back into my body that which I had recently spread on her, made my arousal increase. I licked up the salty essence mingled with the flavoursome wine and licked up the trail I'd left to the peak of her left tit. As I approached the smear of cum over her nipple I felt her hand running up my nylon-clad inner thigh. I engulfed the pointed nipple and heard Dana sigh as I increased the sucking pressure and felt her nipple distend into my mouth. It would only take some of her own warm milk to make this moment perfect.

I lapped at her nipple and the dimpled surrounding thick flesh, my tongue feeling the gooseflesh of her tit. Dana's hand crept up to feel my balls and stroke across my pantied ass and then grip my balls and squeeze them firmly as I moved to her right nipple. The strong squeeze caused a sudden intake of breath just as I enveloped her nipple, sucking it deeply into my mouth. Again she moaned as her hand continued its adventure as I felt a single finger probing at my anal ring. My puckered hole gasped at the contact, clenching on the point of the invading digit that wriggled its way into me to her first knuckle while other fingers scratched along the seam between my balls and anus. It felt wonderful as my cock throbbed to full hardness and my sphincter muscle clenched the finger and felt its size. I couldn't believe how aroused I was again after only minutes since coming very hard all over these wonderful tits. I continued to suck and lap at the tit flesh cleansing it of my cum. As I worked to obey Dana's instruction her finger popped out of my bum and slid around to grip my shaft and commenced to stroke me back and forth.

Her voice oozed her arousal as she said, "Stand up for me; I want to see this hard cock again."

I followed the instruction and stood in front of Dana as she sat up on the couch, her glistening breasts sitting firmly below my hard cock. Her face was level with my erect cock as she stroked me straight toward her mouth. I so wanted to fuck her but it was pretty clear that that would only happen when she was good and ready. She continued to stroke and squeeze the length of my cock as she looked up at me.

"Are you wearing a bra now?" I nodded. "Let me see; remove your shirt," she demanded.

Her huge tits jiggled in rhythm as she continued to stroke me, being sure to use a grip that meant her fingers wrapped neatly around the top of my swollen member and her wrist pummelled against my balls on each downward stroke creating incredible friction. I stripped off my shirt to expose my slight paunch and my sensitive B cup man-boobs neatly held in a peek-a-boo bra that allowed my nipples to poke out. "Oh my what nice nippies you've got. Your sis was right, they do stand up! How sensitive are they?"

Before I could answer she reached up with her free hand and gripped my left nipple firmly between her thumb and forefinger and tweaked and pulled it. I gasped; it took my breath away and my cock throbbed more in her hand as she put more pressure on my balls and suddenly I was coming again. Dana pumped my hard cock in a strong grip and leaned forward to take the head of my cock into her mouth, nibbling my foreskin and grazing her teeth over the sensitive helmet beneath when she pumped her hand down to take the skin out of the way. My orgasm had no cum; I'd spent it all on her tits but the gut-wrench was amazing.

I hadn't come twice in succession so quickly in a very long time. I went weak at the knees as Dana sucked hard on what little fluid she could extract from my wilting member. She released my nipple which had undergone some wonderfully excruciating pressure in the last minute or so. Finally she let my cock go and it flopped down to my ravaged groin where she then neatly pulled my panties back for me and patted it back into place. I stood in front of her, awaiting her next instruction. It didn't take long.

"Well Jason that was very nice. It's good to see you can do as you are told. I do like the under wear but our deal will still be that the more adventurous you get in the office, the more adventurous I will be in response. If you ever want to get into me, and not just my panties or mouth, you will have to think long and hard about how you can impress me! I will see you in your office tomorrow afternoon. Get that mousy secretary of yours to book us some time each day for the next week or so. See you tomorrow."

With that she stood up and left me standing there in my underwear as she walked away to some other part of the house, her breasts bouncing and swaying with each stride as she had not bothered to replace the dress that hung unzipped around her womanly hips. She did not turn or look in my direction; I was dismissed. I gathered my clothes and dressed and left. As I got into my car I wondered what she actually expected if this was to go further and what risks could I take without risking my position at the firm. I guess tomorrow will be another day.

To be continued...