Her First all Male Group


My story begins in 1999 when I managed a real estate agency dealing with clients looking to build holiday homes and hotels plus a separate department dealing with normal house sales.

Teo came to work for us in the homes department as a sales assistant. I took her on as she was lively, highly intelligent and spoke five languages, invaluable when dealing with foreign clients. She had been with us about 6 months before we first went on a date, we got together as a couple almost 1 year to the day after we first met at her interview. To some people we were a slightly odd match as I was older than Teo at nearly 40yrs old.

I had better describe Teo as she was then, 5’3” tall, 22yrs old with straight black hair down to the top of her ass, large green eyes and Italian/Spanish looks. Her body is superb, long shapely legs for her height, tiny 22 inch waist, 34D tits with average size dark brown aureole and large dark brown nipples, she was always fully shaved, apart from her head there was not another single hair on her body, fantastic to look at and lovely to go down on, I spent many happy hours using my mouth and tongue on her wet and willing pussy.

Her face can only be described as stunning with a small nose and full lips, when she smiles the room lights up, her big green eyes sparkle when she gets excited and she loves sex, altogether an intelligent, very lovely and very horny package with an outgoing and friendly manner.

When at work she always dressed in a sexy, sophisticated style, usually with a white blouse with one too many buttons undone to make the most of her tits, which looked bigger because of her small slim build. Teo was great with male clients, the way she flirted with them, touching their arms and hands and looking directly into their eyes with her full smile had them very willing to deal with us. If it was an all male group of investment company reps she would flirt outrageously with them to get the deal done.

None of which ever bothered me, we often ended up having very intense sex sessions in the evenings, with me teasing her that she would find herself in the middle of a gang-bang one day. This type of talk, of her being fucked by several men seemed to turn her on, making her pussy very wet and ready and usually ending with a huge orgasm for us both.

So how did Teo end up making my teasing, and to be honest our secret fantasy come true? We had been working hard to complete a project with an investment group from the European Union and had finally completed the deal on a Thursday afternoon, everybody was relieved to have finished early as they wanted to travel back home over the weekend.

But before they left they wanted a night out at a club to celebrate, and as they confided in me, maybe find a one night stand with some willing woman. I thought they stood a good chance, they were a group of five businessmen aged between 28 and 55 yrs old with money to spend.

After consulting with Teo and a couple of people in the office we ended up recommending a local club that had a reputation of being a bit wild and good for finding single women out for a good time. They made it obvious they expected us both to be there to celebrate with them, so before they left to go to their hotel to eat and get ready we arranged to meet them at the club at 11pm, giving everyone plenty of time to prepare.

Teo and me went home early and managed to snatch a quick couple of hours sleep before getting ready to go out. I dressed in my Italian black suit with an open neck plain white shirt and black shoes and sat in the lounge with my gin and tonic to wait for Teo, I had taken her large G&T up to our bathroom for her where she was preparing herself.

When she appeared in the lounge she was wearing one of her favorite dresses, a tight cocktail mini dress in bright green to match her eyes, it was made from some sort of stretchy material that clung tightly to every curve of her body. It had a scoop top, being stretchy this could be pulled down off her shoulders to sit further down her arms, exposing as much of her ample 36D breasts as she wanted too or be pulled up to form a modest scoop. The hem finished about 2 inches below pussy level, exposing nearly the full length of her lovely legs. I knew from experience that when she sat down she needed to be careful if she didn’t want to show her knickers to anyone watching. She had no stockings on leaving her tanned legs bare and had put on her black 6inch heel stiletto’s with the ankle straps, what she called her fuck me shoes. My comment of ‘Wow’ brought a big sexy smile to her face and she pulled up the hem to show me she was wearing a very tiny G string that was just a bit of black lace at the front held together by very thin strings. I was surprised and told her so, she explained that with this tight dress it was either full size knickers or virtually no knickers, as anything in-between could be seen in outline, which she hated. For the same reason she had no bra on and her large nipples escort were making little tents in the thin material. I had to agree with her and looked forward to seeing how she would protect her modesty when sitting down with the guys as crossing her legs would expose the full length of leg and even a bit of bum cheek to their gaze, she would have to be very careful.

We arrived at the club just after 11pm and the guys had found us seating in a high-back booth with a fixed oval table in the middle, they had even found a chair to place at the table end making enough room for all seven of us. One of them called over our waitress and ordered another round of drinks telling her to make them large ones as nobody was driving that night. Teo squeezed onto the last vacant spot in the booth, sitting with her legs crossed and pointing inwards, leaving me with the chair.

I looked around the club, noting the dance-floor right in front of our booth and the private rooms along one wall with privacy glass at the front which allowed the occupants to see out without being seen themselves. On the floor above them was the VIP area also with privacy glass where I had heard that local sports team’s and other business big-wigs could party unseen by prying eyes. What I didn’t know was this area had it’s own private entrance as well so nobody would have to pass through the main club area, all very discreet and therefore popular with the more well known clients.

When the waitress returned with more drinks I asked her about the possibility of booking one of the private rooms for the evening and she said she would ask the manager. She returned to tell me that unfortunately they were all booked but if anyone canceled we had first refusal. When I told the others they were a bit disappointed as they had hoped to be able to entice some other girls to join us for champagne in privacy, but resolved to make the most of the night.

They ordered two bottles of champagne anyway and after it was opened we all drank a toast to the success of their venture. The champagne coupled with the G&T’s me and Teo had already consumed was making me feel a bit tipsy but still well in control. Teo I noticed was becoming very flirty with the guys closest to her as the drinks took affect, a tendency I had noticed with her when out partying. One of the younger guys asked Teo if she would dance with him, she looked at me before answering and when I told her to go ahead she linked arms with him and off they went to the dance floor.

The older guy asked if I minded her dancing with other men and I explained that not being much of a dancer myself and also being 18years older than Teo it seem overly protective of me not to allow her to do something she loved. Teo is a very good mover, getting into the mood and beat of the music and being very uninhibited, even exhibitionist, in her dancing while loving the attention she gets when on the dance floor. I moved into the seat she had vacated so that I could watch them dance along with the other guys.

They stayed on the floor for two dances and as they made to return another of the younger guys jumped up and stopped to speak to Teo, who turned around to return to the dance floor with him and started to gyrate around again. A couple of the others asked if they could join them leaving just me and the oldest guy to sit and watch. They all grouped around Teo and she was loving the attention as they took turns to hold and touch her as they moved to the music. The chap I was with asked if I ever became jealous of the attention that Teo received and I explained that when you are involved with someone like Teo you had to expect other men to pay her a lot of attention, but at the end of the day it was me she went home with, not them, he just laughed and said ‘Good attitude, I like that’.

During the next couple of numbers I saw our waitress take Teo another glass of champagne on the dance floor, unusual as I hadn’t noticed her pour it from our bottles but assumed one of the other guys had ordered it for her. Three songs in the music changed to slow mellow mood sounds to give everyone a break, but instead of leaving the floor Teo grabbed two of the guys around their necks and started to sway between them in a slow, slow dance, the other two she persuaded to join in front of her making a tight little circle all moving together. The two either side had their arms around her their fingers gripping her small waist as she swayed between them. The two in front had moved tighter leaving no gaps so that all that could be seen was four men and one girl in a very tight group.

When the slow numbers stopped they all returned to our booth, except this time Teo squeezed in first sitting next to the older guy and the others sitting either side of her with her in the middle. I vacated my position and sat back in the chair facing them. They all drank more champagne and two more bottles were ordered.

The manager came across and asked if we were all OK, I explained we were disappointed about not having a private room but understood he had to cater for the people who had pre-booked them. He said we obviously had money to spend and he would, if we wanted, open the VIP area for us as they had no special bookings for that room, the only rule being that they only served champagne in there but we were drinking that anyway. Our five clients quickly agreed to foot the bill and the eldest one gave the manager a company credit card to cover all expenses for the evening. The manager asked us to wait for ten minutes and he would send our waitress to fetch us when the room was ready.

She arrived after just five minutes to escort us to the stairs in the entrance annex that led up to the VIP room. When we entered we found seating for over thirty people, all on very comfortable sofa’s in a dark material along one wall, set out as three groups of tens in a semi circle with a low solid wood coffee table in the middle to place drinks, champagne buckets and anything else on.

Our two new bottles of champagne stood on the table of the center group of ten seats. To our left were windows of privacy glass running almost to floor level that allowed us to see into the main club area, to our right was a smaller dance floor with both underfloor and ceiling lighting, a chrome dance pole was slightly off-set to one side and another large sofa with seating for about six sat facing us from the back wall of the dance-floor.

We all settled into seats with Teo in the middle of the U shaped seating and the rest of us spread out around the rest, I deliberately sat on one of the end seats as I wanted to see just how far she was prepared to let the flirting and touching go. As she sat her dress rode up exposing the tiny black lace triangle of her thong, I thought I saw a bit of moister as it pulled into her pussy outlining her vagina lips in the paper thin material, my cock started to get hard from the sight and I was willing to bet I wasn’t the only one getting hard. Teo seemed oblivious to the show she was putting on and leaned back in the seat exposing even more of her charms as she chatted with the two guys either side of her.

While talking to them she had her hands on their legs and made no objection to them putting their hands on her bare legs occasionally, she even lent across one to say something to him, her bra-less breast squashing down on a hand as she did this.

The manager arrived to check all was well and asked if he could have a word with me in private, so we went across to the bar. Once there he asked if we were new to the club, which I told him we are and related how we had chosen to come here on recommendation, then explained about the real estate business and who the guys were, pointing out that they hoped to have some fun before flying home. He told me the club was run on hedonistic principals and anything that happened in the VIP area was not spoken of outside of the club and he hoped we would respect that rule. Then said that everyone generally came to the club for a good time and if some suitable women came in he would send them up here for the guys to enjoy their company if that was OK with us.

I told him that would be great and in future I would bring my more wealthy clients here to relax, as well as returning ourselves, I had been looking for a decent club for some time, rather than a boring disco type place, to bring clients too on a regular basis.

He then asked if he could ask a personal question, I nodded and told him to go ahead, he asked ‘Is the girl in the green dress your girlfriend or just somebody from your office’? Laughing I told him who Teo was, and that despite the 18yrs age gap we were in fact a couple.

He then asked, ‘Are you OK with her dancing with the other guys and flirting with them’?

I replied, ‘I am as she was very flirtatious and outgoing anyway and usually closed the deal when male clients were the buyers’.

Has she ever gone further with them? He asked

Not as far as I know, maybe a bit of ass fondling but no further yet. I replied.

He quickly picked up on the ‘Yet’ bit of the answer.

Do you think she wants too? Do you want to watch her fuck with another guy?

I explained that we had often spoken about it and she usually had a very wet pussy when we used the fantasy in our foreplay, and yes I often thought of watching her fuck another guy, I just wasn’t sure about a gang-bang, or what her reaction would be if it came to the crunch.

We can make it happen, he replied, if you really want it too, give it some thought and come and see me later when you are ready.

Intrigued by his reply I returned to the group.

Things had progressed from when I had left.

Teo was still sat in the middle of the group, her dress had ridden up and her lacy thong was clearly in view as I sat down. She had her arms around the waists of the guys either side of her, which explained why her dress had ridden up, they both had hands on her bare thighs and the scoop top of her dress was now halfway down her upper arms. Her ample bra-less bosom spilling half out of the top, nearly exposing her nipples, the edge of her dark brown aureole just visible, one little tug and her nipples would pop into view, which were already very hard and sticking out.

Teo was a women in an aroused state of sexual excitement, it showed in her body and her eyes, she was loving being the center of attention, it appealed to her vanity as a stunning looking sexually aware young woman to have a group of five men lusting after her.

She looked me straight in the eyes and I could read the excitement in them as she bit her lower lip with her teeth, almost pleading with me in her expression to allow it to go on.

In that instant I decided to allow her to go for it, my hard cock was telling me, let her fuck with them, I wanted to see her as she orgasmed with a hard cock deep inside of her pussy, her hips thrusting hard against whoever she was fucking with.

Just then the music in the VIP room changed to a slow number and she was pulled to her feet by two of the guys who guided her towards the dance floor.

As soon as she left I asked the guys to excuse me and went to the bar where the waitress was, asking her if she could get the manager for me. She picked up the in-house telephone and spoke to someone, letting me know he would be a couple of minutes.

I turned around to watch Teo and the guys on the dance floor, the underfloor and ceiling lighting making it easy to observe from the floor area. Teo was now dancing, if you could call it that, with all five clients. She was again in the middle of them, this time her arms were around the waists of the guys either side, their inner arms were over hers trapping her arms at waist level, their hands holding her waist on either side as they slowly moved around. The other three were in front and taking turns to be in front of her with the other two blocking the view, I suspect they were trying to hide what was happening it that tight little huddle.

I realized why when I saw that the top of her dress was now down to her elbows and almost at her waist, given she had no bra on I knew her 36D tits with their big hard nipples were now out on show to them, the tilt of their heads as they looked down confirmed it for me. I felt a surge of jealously then and almost moved to go and stop it, but the manager spoke to me, diverting my attention from the dance floor action.

He asked how he could help and I asked what he meant when he said he could make a gang bang for Teo happen.

His answer shook me a bit when he explained that they kept a form of female liquid Viagra behind the bar just for occasions like this, when groups of VIP’s and stag parties wanted to fuck willing women who just needed a little push to really go for it.

The question was did I really want this?

There was little chance of turning this around later.

My mind was split between jealousy and lust, my rock hard cock won out and I told him to go for it.

He spoke to the waitress and she poured a glass of champagne and using a bottle put five drops of clear liquid into the glass before giving it a swirl with a cocktail stick. Putting it on a tray she took it across to Teo on the dance floor, asking the guys to move slightly so that she could give her the glass.

As they parted to allow her hand through I saw Teo’s bare tit’s in the light, I could even see her hard nipples sticking straight out from the up-turned tips.

I watched a hand cup her right breast and pinch and roll the nipple in the fingers as Teo reached for the glass. She looked across to me and raising the glass she swallowed the lot in one go before handing the glass back and turning her attention to the five guys.

That brief glance had my cock twitching and if possible it grew even harder and bigger.

It was now obvious that the guys were taking turns in either holding her arms or moving across in front of her to fondle her tit’s or tweak her nipples, and Teo was loving it, judging by the fact she was making no attempt to stop them.

I wondered if any of them had yet dared to slip a hand under her skirt to feel what was probably a very wet pussy.

The waitress came back and asked me if I had seen what was happening, I told her I had briefly seen her tit’s and nipples being fondled. She said that when Teo had taken the glass and tilted her head back to drink the contents a hand had been under her skirt and was obviously rubbing her clit and pussy.

I asked her how long would the Viagra take to work and she said on average 15 to 30 minutes, she then told me the drink she had given Teo when she had been dancing downstairs had just three drops in it as well, as the manager had suspected what might happen, he was apparently very good at picking up on the moods of the groups in the club.

I sat by the bar trying to control my lust as I waited to see what would happen next, trying to keep an eye on the dance floor without staring intently.