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Successful Day At Races

"Big Win"

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This is a true story that happened twenty years ago. At the time obviously it was exciting, then afterwards for years I felt ashamed of myself as it was so against my normal behaviour, now I realise how lucky I was to have such a sexual experience and am now looking to experience similar experiences with my partner. I was thirty two years old at the time with a nice figure, definitely not affected by my four pregnancies. I was often hit on by males half my age. That is a now a secret desire of mine to sleep with someone half my age.

I was recently divorced mother of four children, aged from five years old to ten years old. It was a rare weekend when I was child free, as they were all at the father’s place. I took the opportunity to go to the local horse races for the biggest event of the year - being the local Cup Race Day. The town swells in population over the few days surrounding the Cup Races. I arranged with my best friend, who I will call Katie, to attend the races together, and then join the majority of the race day crowd back at the local Club to continue drinking and dancing until close.

Being recently single after ten years of marriage had me wondering what the Race Day would bring. Would it be strange as I was used to attending the event with my ex as a married woman or would it be the opportunity to potentially test the waters and find myself a one night stand?

Katie and I enjoyed a day at the races drinking and socialising with no real indication that the evening would lead to anything except an evening of drinking, dancing and socialising. We had caught up with many friends throughout the day and were sure to catch up with many of them again during the evening.

As I lived very close to the Club where we would spend the evening, between the races and the club I intended going home and changing into something more comfortable. After catching the free bus from the races back to town, Katie and I went to my place so I could change out of my race attire which was a fancy dress high heels and a fancy hat. I quickly changed into something more comfortable, a nice blouse and figure hugging jeans were the choice with some comfortable knee high boots.

We quickly made our way to the Club where we would spend the evening. I must say I was feeling very sexy in my outfit and with the consumption of quite a lot of alcohol throughout the day and the presence of some well dressed men I was feeling very horny. Was this the night that I would jump back into the saddle after my marriage split.

While going to the bar I ran into a guy I knew, a local builder Bob and his mate Bill. We chatted whilst in the line waiting to order drinks. I didn’t pay much attention at the time but the wait must have been quite lengthy as Bob was able to learn that I was now single and living only about a street away from him but in the same direction. Once we had ordered and received our drinks we went our separate ways. I went back to Katie and socialised with others that we had joined up with.

On a few other occasions, either by chance or clever planning by Bob, we met in lengthy lines waiting to order drinks. This meant we had plenty of time to talk. He even bought me drinks and insisted on walking with Katie and I at the end of the night so that we would arrive home safely.

Still there was not much said outside of innocent chit chat, however now looking back he was quite flirty and did give me lots of compliments.

The night crept on and the Club was closing so we were organising to leave. Katie and I were being accompanied by Bob and Bill had left, or so I thought. Katie's house was first so I walked her to her door and said goodnight. Then Bob and I continued to my house and it was only when I got to the front door that Bob asked if he could come inside.

I said yes not knowing if I wanted something to happen or if I expected anything to happen or whether I was naive thinking this was all innocent. I think I knew exactly what would happen if I allowed Bob inside. Or so I thought!

I opened the door and went inside. Bob followed and pushed me up against the wall and started kissing me. It went on for sometime and I was feeling increasingly aroused and horny as it had been sometime now since I had been intimate with anyone and the last person I had been intimate with was my ex husband. By this time it was one in the morning and I was surprised when there was a knock at the door. I walked to door and opened it. Bill was standing there and i said, “What do you want?”

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He then asked, “Can i come in?"

Before I could really answer he proceeded to come in, closed the door behind him and he saw Bob standing there.

Bob did not really look surprised nor did Bill. Bob again grabbed me and continued to kiss me. I was enjoying being intimate with Bob and I guess I was lost in the moment. Bill started touching me from behind and started grabbing my bottom and then rubbing my pussy through the denim of my jeans. I guess Bill sensed I was accepting when I did not turn him away and instead parted my legs a little. Bill then started to undo my pants and take them off. Bob undid my top. So now I was standing there in my hallway just inside my front door in nothing but sexy black lace underwear with two men touching me in places that hadn’t been touched for some time and certainly hadn’t been touched by another man except my ex husband for about thirteen years. To my surprise having never done anything like this I was very into this and didn’t think of objecting or stopping for a moment. This was by far the raunchiest thing I had ever done.

My nipples were rock hard and I could feel how wet I was. I then suggested we go to my bedroom where we all got naked and climbed into bed.

I was kissing Bob with Bill watching, then swapped and was kissing Bill while Bob watched. Both were good kissers and the whole experience for me was quite erotic and such a turn on, as I love kissing and foreplay.

Although my initial connection was with Bob, and I found Bob the most attractive and more to my liking, Bill was the aggressor.

Bill took the plunge and positioned himself between my parted legs. While he positioned himself, Bob reclaimed my hungry mouth and resumed passionately kissing me.

Without delay Bill slid the head of his cock inside my wet pussy and started to rhythmically increase the speed and depth of his plunges. My ex husband was a very fulfilling nine inches and neither Bill or Bob were close to that. However the excitement of passionately kissing one guy while being fucked by another was out of this world.

Bob was now not only kissing me passionately but also kissing biting and pinching my nipples. I could feel the climax building inside me and it wasn’t long before I had my first incredible orgasm almost simultaneously with Bill planting his seed deep inside me.

Bill now pulled his softening cock out of my satisfied but wanting pussy and shifted positions to allow Bob to position himself between my legs. While Bob massaged my clit and gently eased his slightly larger cock than Bill's inside me, Bill and I kissed passionately. Bob felt so good as he took centre stage inside my hungry pussy. Bill was obviously enjoying the experience and was hard again in no time at all. I took his cock in my mouth and for the first time ever enjoyed a blow job at the same time as I had my pussy wrapped around another man’s cock.

Bill was the first to cum, followed by Bob and I sharing an intense orgasm at the same time. I think Bill realised there was a stronger connection between Bob and I and he gave us a little space and watched from a distance.

I was still hungry for more and sucked and played with Bob until he was hard again. Then I climbed on top of Bob and eased my pussy down onto his rigid cock. We passionately kissed and he fondled my tits until I started to ride his cock like a woman possessed. This felt so good I could feel an intense orgasm building and I was screaming for him to fuck him harder and make me cum like I never have before. He clearly took up the challenge and we for the second time shared the most incredible orgasm together.

When we both recovered, Bob dressed as by this stage Bill had already dressed. I accompanied them to the front door were I shared some passionate kisses with both Bob and Bill.

They both left and we never repeated the experience or were in touch after that.

For years I regretted the night. It wasn’t until I shared the experience with my current partner and lover, the only person that I’ve ever shared the experience with, that I realised how much I really enjoyed it. My partner is extremely excited and aroused by my experience and wants to share a similar experience both with another male and another female.

I get so wet and aroused when we talk about it, so it’s no longer a question if I ever have a threesome again but more a question of when and whether we will share with a male or female first but we will certainly try both.

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Written by MrHuge2024
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