When I had not long turned 20, I was having the time of my life. I had a fun job, good friends and a thriving social life for the first time. It was with this backdrop that I agreed to go on my first ever girls holiday with some friends from the pub I worked at and a few people they knew from elsewhere. In total, there was 11 of us. I knew 6 from work and had met the other 4 but couldn’t claim to know them properly.
The group was primarily aged between 20 and 23 but Jackie (someone I didn’t really know) was 38. She was loud, crude and on the holiday to get over her divorce the previous year.
We all piled into two minibuses to take us to the airport and the silliness started straight away. The jokes continued when we got to the airport and it must have been clear to anyone within a mile of us what kind of holiday we were going on.
Once we were through security and faced with a long wait for the plane, we went for a drink. As we all settled down a bit, one of the main organisers of the trip stood up and announced we were going to draw names to see who shared rooms with whom. One of the girls had a medical issue and requested the single room and everyone was happy with that. That left ten people and five rooms. All of the names were on bits of paper and a young lad clearing tables was roped in to pull names. Mine was the first to come out. I was excited to see who I was going to spend a week in a room with but was slightly intimidated when Jackie’s name was pulled next.
Jackie straight away sat next to me and said we would be best friends at the end of the week as long as I could put up with her bad singing and (she said this bit with a knowing tone) said I could keep secrets. Everyone laughed and I joined in but I knew I wasn’t going to get much in the way of relaxation on this holiday!
The flight went smoothly, the transfer to the hotel took way too long but it was soon night time and we had just finished checking in and getting settled. We were all tired so we had a quick bite to eat in the hotel restaurant and went to bed. So far, so quiet.
Our first full day was spent on the beach or in and out of the seafront bars. I was surprisingly comfortable in my first ever bikini and my 32DD boobs and little, pert bottom were getting me some attention. I didn’t consider myself the cutest of the group considering there were some absolute stunners amongst us but I liked being seen as sexy. Jackie was quite vocal about how she thought I should be taking advantage of the looks I was getting and how she wished she was getting half as much. She was more hips than boobs but had a MILF softness about her body without being overweight. She was getting her share of the looks but she was the type to always want more.
For our first night, we kept things simple. A light dinner was followed by a few bars. We drank, danced, laughed and messed about. People started to drop off and head back to the hotel but some of us stayed out to continue the fun. Jackie and I ended up dancing in this bar and when we got back to our seats, a couple of drinks were sent over from the bar. Jackie scanned the crowd and a man raised his glass towards her to indicate the source of our refreshments.
Jackie was very excited by this but told me to act cool as we walked over to thank them. The men were in their mid-thirties at a guess and spoken with very thick, London accents. They seemed cocky and brash but funny with it. We had a few drinks with them (we bought our own after that) and had a laugh until I said I wanted to turn in. The men asked us to stay and I expected Jackie to cause a bit of hassle but she backed me and said we should go back to the hotel. We thanked the men for the company and walked back with us both laughing over Jackie’s crude jokes about which one she wanted. I was relieved that she was on my side and felt more relaxed from then on.
The next day was pretty much the same and we spent the evening in similar places to the first. It was getting late but we weren’t slowing down when I heard a familiar voice. One of the men from the previous night was talking to Jackie and, when she noticed me, she called me over. We had a laugh and a couple of drinks when Jackie dragged me off to the toilets. When we got in there, Jackie made it very clear that I could say no but that she wanted the shorter one and the taller one fancied me, was I willing to go back to their suite with them? She said it was OK if I didn’t want to and that she would stay too if I did. I wasn’t too sure but I was there to have a good time so I thought why not? Jackie was very excited by this and she practically skipped back to them like an ebullient schoolgirl.
As we got back, the men asked if we wanted another drink. Jackie answered for us by saying yes but should we have in at their place. The men caught on and we were soon walking back to theirs. Jackie was all over her man. He was about 5’8, slimmish, tidy brown hair and a swagger instead of a walk. My guy was about 6’, shaved head, a full sleeve of tattoos and seemed more reserved but carried himself with a lot of confidence. He didn’t attempt to put his arm around me or anything like that but walked alongside me and we shared a few jokes. His smile was very disarming and I was finding him more attractive now we were out of the hustle and bustle of the bar.
They were staying in a much posher hotel than us and their suite was very nice. There was a living room with balcony, a bathroom and two separate bedrooms. We all congregated in the living area with Jackie and Ben sat on one sofa and me and Craig on the other. We had a couple more drinks and Jackie rather unsubtly said that their suite was lovely and that the bedrooms must be really comfortable. Ben did not miss this mountain of a hint and they were soon disappearing through the door for a ‘tour’. This left Craig and I sat in the living room. I knew where this was going and I was happy with it, but I had no idea how to take the next step. Craig removed the indecision for me by nodding towards his room and simply asking ‘shall we?’
When we got in the room Craig closed the door softly and approached me. He put his hands on my hips, I lifted my face and he leant down to kiss me. It was gentle at first but the passion soon built up and it wasn’t long before he was pawing at my tits through my dress and bra, both of which were soon discarded. Craig pulled his shirt off and I sank to my knees as he fumbled with his belt and pushed down his trousers and boxers. His cock was the biggest I had seen and looking back, it must have been about eight inches long and nicely thick. He was semi-hard at this stage though so the thickness was evident but the length was still to come.
I took the base of his cock in my hand and slowly stroked his shaft. I could feel him getting harder and harder before I finally put the head in my mouth. I found the thickness hard to deal with at first but he didn’t pressure me, he let me find my way and navigate my own oral path. He was groaning and moaning in a guttural, manly way as my depth and pace sped up. My tongue was teasing him but he didn’t say anything until finally whispering ‘that’s it girl, get it nice and wet’. I didn’t really know that wet was a desirable thing for a man at that stage but I made my blowjob as sloppy and spit-covered as possible. Before long his cock was glistening and I had spit dribbling down my chin.
Craig stopped me and told me to lie on my back on the bed. I thought he might want to eat me so I pulled my knickers off but instead he knelt near me and shuffled up to be alongside my hips. I had no idea what he was planning and I think he could see the confusion on my face because he asked if I had ever given a tit wank before. I had never heard the term and shook my head. He said he would be gentle and straddled my stomach with his cock coming to a rest between my big tits. He told me to push my tits together around his cock and he slowly started thrusting his cock between them with my spit as lube.
I felt very passive in this situation. All I could do was look down and see his reddish-purple cockhead appear and disappear from between my tits. It was almost hypnotic and I missed all the signs he was close because soon his thrusts got harder and his cock exploded cum all over my face, neck and chest. He grunted with every spurt, looked down at me with a smile then climbed off me. I felt like I was in a state of shock when he came back with a towel for me to clean myself up. I wiped myself down and Craig padded off still naked to get us some water.
When he got back we lay together and talked about nothing in particular. He said he loved my body and how slim I was but with such big boobs. He fondled and stroked my tits, his hands eventually sliding south until he found my pussy. We kissed as he fingered me with some skill, bringing me to the edge of orgasm. Just as I could feel my orgasm about to hit, he pulled his fingers from me and told me to get on top. I told him to find a condom which he did reluctantly. I straddled him and slid down on his thick, hard cock. I moved my hips and bobbed up and down in turn as Craig alternated between squeezing my boobs and watching them bounce.
Suddenly, Craig sat up with me still on his cock, grabbed me in a bear hug and rolled me onto my back. His cock somehow stayed in me and, when we were in the missionary position, he started to fuck hard and fast. He didn’t last long like this and he was soon filling the condom with his second load of cum. He rolled off me panting and thanking me for a good fuck while I lay there wondering if it was rude to bring myself to orgasm because it was obvious he wasn’t going to do it.
After about ten minutes I heard movement in the living area and, with Craig drifting off to sleep in bed, had a peek to see what was happening. Jackie was naked but dressing just outside the other bedroom door. She spotted me and told me to grab my knickers, we were going. I happily and hurriedly dressed and we made our way back to our hotel.
We compared notes on the way back and it turns out Ben spent most of their time either being blown or trying to get anal. Neither of us had a particularly fulfilling night but we agreed it was still fun. Jackie must have blabbed something though because the girls called me Titwank for the rest of the holiday!
Source: reddit.com/r/gonewildstories/comments/cl57vp/holiday_sex_mf