Tommy had made most of the arrangements in the end, he'd booked the villa and the flights, invited friends, arranged trips out and games of golf. The only thing it really fell to me to arrange was to invite a friend of my own.
"Bring someone fun." He'd told me.
So I invited Tabby. We'd been friends since school and had learned about everything together, and I do mean everything, so we were very like-minded. We had our own little quirks though, she was more on the lesbian end of the bisexual spectrum than I was although you wouldn't know it if you ever saw her going at a cock. She always described herself as a lesbian who loved cock.
"I'm not attracted to guys, I just like shagging them." I remember her saying back when we were at school.
We'd done so much together over the years and Tommy knew her well, intimately in fact. I had a feeling it was someone like her that he'd had in mind. She was gorgeous too; her parents were Chinese immigrants and she had that petite eternally young thing going on.
"Where are we going? I need to know what to pack." He just grinned at me and came back.
"Puglia sweetie, southern Italy, but don't worry too much about packing. I've bought you an all-new wardrobe; outfits, jewellery, shoes, the works. Be a good idea for you to sort out your make-up and any other little bits you want but you don't need to pack any clothes. Tell Tabby the same by the way."
Well that was a turn up for the books. Money was never an issue so I had no problem believing he'd have spared no expense but couldn't help wondering why he was doing it this way. He usually loved my choice of outfits and knew I could be relied upon to wear things that would please his friends. I shrugged it off and went about my day.
As departure day approached I started to feel that wonderful mixture or nerves and anxiety. Golf trips with Johnny's friends always involved a lot of sex and with Tabby in tow I expected there would be even more! I went about packing a good selection of make-up and then some toiletries (gotta have something to help with the clean-up!) I couldn't help noticing that there wasn't much other luggage being generated. Tommy had one case and his golf clubs, but I didn't see anything else.
"Where's all the stuff that you promised for me and Tabby?" I asked.
"Don't worry hun, it's all in hand. As all your things are brand new, I had them shipped straight out there. Besides, I couldn't risk you finding them and ruining the surprise now could I?"
Again, this seemed strange but I shrugged it off and spent the rest of the day in the garden. The sex that night was frantic. Tommy was on top with my legs wrapped around his waist and my arms around his neck. He was far too eager; pounding away hard and fast he overstimulated himself and came in minutes. At first I was disappointed but he was clearly very excited about the trip because he was on me again after a very short rest. Short bursts are great when they're as frantic and passionate as this was and it was during the fourth round that I eventually came. We collapsed in a heap, so sweaty and smelly that I genuinely considered changing the sheets before going to sleep.
"You're going to have to pace yourself if this holiday is going to go the way I think you want it to..."
He just threw his arm over my chest and kissed me on the cheek as we lay there together. We were both asleep in minutes.
The doorbell rang fairly early the following morning, it was Tabby meeting up with us for the flights. She came on in while Tommy and I gathered the last few things together. I've never understood why, no matter how much organising and preparing you do, the morning of a flight always seems like chaos. We were just about ready to go, I just had to put some clothes on, when Tommy handed us each a bag.
"If you're game for it, I'd like you to wear these outfits for the flight."
Immediately I knew what this was about, he wanted us dressed slutty for the journey.
"Bright red glossy lipstick would be good too."
We looked in our bags, rummaged a little, then gave each other a grin. This was going to be fun. Tabby began to peel off the shorts n tee she'd worn for the day, which was already quite sexy but nothing compared to what was in the bag. I was already naked, I hadn't bothered getting dressed after my shower. I stepped one foot and then the other through the tube of fabric that barely qualified as a dress. It wasn't the smallest of it's type I'd ever worn but it was far from classy. With the top hem a few inches below my armpits the bottom hem was barely an inch below my buttocks. I stepped to the mirror to see the effect. I wasn't worried about anything popping out but that seemed academic. The bright red fabric clung so tight that nothing was left to the imagination. I stepped into the equally bright red stiletto shoes which had a good inch of platform below the toe. Sure enough with the diamante earrings and necklace that were also in the bag added I looked exactly as I imagined a high end prostitute to look.
Feeling quite turned on by the overall effect I turned and looked at Tabby and found myself even more so. Her shoes were the same red stripper types that I had but her dress was very different. Essentially in two parts, the skirt was super tight and barely covered her ass. I had half a mind that as she walked it would ride up and show some meat. The top was a backless halter neck and didn't have much width. Standing to the side you could see a substantial amount of her 34Cs. The fabric on the top was really loose too, it was going to fall open and as she moved her boobs were going to bounce wildly.
Tommy was looking very pleased with himself.
"Are all of our outfits going to be like this?" Tabby asked.
"You'll have to wait and see I guess." Replied Tommy. "What do you think, you feeling ready to travel?"
"Never felt better about it." Tabby smiled.
"I can't wait to get started." I chipped in.
Tommy took our small bags and put them in his case so that we didn't have to carry anything and we headed to the airport. As we walked into Heathrow, a heaving mass of people as always, we drew the usual array of different looks from people that we always got when we were playing exhibitionist games. Most of the men would stare or nod approvingly, the tired looking mums with screaming kids would disapprove, the older folk usually sniggered but honestly most people just looked away and ignored us. After we waited for Tommy to check the cases we headed for security where a towering wall of black muscle stared at us as we passed through the gate. I've never wanted a cavity search so badly in my life! Then as we progressed in we found the other guys at a bar. They cheered loudly as we approached, I couldn't help noticing how Tabby tits moved beneath her dress as she walked toward them. She was loving it though, judging by the huge smile on her face.
Eight guys I counted, plus Tommy made nine guys and two girls. This was going to be a demanding week, but I couldn't wait! We had a drink at the bar with everyone introducing themselves; there were a few I didn't know and only a couple of them knew Tabby. It was a very handsy meeting with lots of admiring of the outfits, 'checking out how nice the fabric feels' and then just flat out groping. By the time they called our gate I was horny as hell. We tottered over there and there was lots of excited chatter as we waited to board. It was only as we boarded that Tommy handed Tabby and I our tickets. They guys were all in first class and we were in economy, what's more we weren't even together! At first Tabby was annoyed calling Tommy a cheapskate but I knew exactly what this was about; he'd dressed us as sluts and then sat us next to complete strangers just to see what happened. It was only about three hours to Puglia, but a lot can happen in that time.
I found my seat, it was a window so whoever was next to me was going to box me in. Deliberate no doubt. I didn't have anything to stow so I just sat down. I looked across at Tabby, also in a window seat and there was this older woman, late sixties I would say, preparing to sit next to her. She was a quite pretty for her age and a well-kept sort so that would be interesting. I doubted it was going to turn into a lesbian romp but it could well prove uncomfortable if she were the disapproving kind. Then my partner arrived. Another very average looking person but a guy this time, in his mid-forties I would say, wearing jeans and a shirt. He looked at me and seemed very pleased with his allocated seat. I have to say I was hoping for something better but realistically it was exactly what I expected.
We sat in awkward silence while all the usual pre-flight and take-off stuff happened and even once we were in the air he was quiet. The flight attendant came around and I realised I had nothing to buy a drink with, and 'oh boy' did I need one. However my new neighbour piped up for the first time and asked if he could buy me something.
"Uh, sure. Whatever you're having."
"Four whiskeys and a can of coke please."
Taking the two plastic glasses he emptied two whiskeys into each and topped them up with a little bit of coke.
