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(M)y first experience
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The following is a true event and my first experience with both a group, being exposed and major age gaps.

I went to a event I saw on "Meet up". This was a dating/ learn about adult experiences event. I did not realize this was for men and women older than 20s. The first half of the night went okay basic speed dating/drinking, I was wearing a dress shirt and tie (I overdressed). After the speed dating part the host talked about good boundaries and how to explore new ideas within a relationship. Then we went back to some group ice breaker games. During one of the rounds the question was, who has had sex since their last birthday (half the question were x rated) I was the only one who didn't take a drink. It had been 3 years since my last relationship. Later that night the group went next door from the restaurant to a bar owned by the host. There were about 30 people in the bar, 14 being my group. I slowed down on my drinks and began to sober up. One of the group members had a pair of handcuffs on them (no idea why). Three of the group (2 girls and a guy) ask me about my sex life and I was loose lipped about it(darn booze). When then found out I'd never be with a woman older than me one of them (asian girl 40s) started physical hitting on me, I was getting excited, at this point it was obvious I was turned on. One of the guy suggested the ladies have some fun. It was obvious I was nervous the bar tenders (young woman earlier 20s and 30ish guy (our host bf) heard us, the guy said "your Mary's group" when we yes, they smiles and said the bar is all "adventurous folks" and that no one will mind if we explore alittle and gave us a round of shots.

Feeling braver I let by hand slide over to the woman next to me who took my hand and slide it under her skirt. I was shaking little. I'd never been up the dress of an older woman before. She whispered "relax, enjoy this" it was at this point that I saw the look on the guy across the table and realized he was stroking himself with the help of the other woman. They both looked at me and I felt a new feeling of shame and excitement I'd never felt better. The Mary came over to the table say everything and only say "glad your all getting along, and don't worry no camera in her" she then went around and offered all the guys those individual blue pill packs... asking if we want some I said nothing by the girls took from her and put in our next shot glass. At this point I was feleing good, was getting excited and had my hand in a beautiful place. The lights in the bar were turned down and I saw Mary turn the close sign before locking the door. She then told everyone that it was time to enjoy the night (i learned later that this was a swingers event). . I'll cut some details to save time

A little while later after I admitted i had never been open to pay with others but wanted to, I ended up on the pool table, in my shorts, with my 🍆 and balls pull out of the front. I was on my knees (kneeling on the pool table) with my hands in the fuzz cuffs behind my back. Some couples in the group had gone off to play but I there for all to see, there were about 20-30 folks left in the bar, mixed group (our speed dating group, bar regulars/swinger, the 2 bar staff and Mary... who was "helping" 2 of the couples).

I agreed (after some encouragement to) let people show me how it felt to open myself up to others . So for the next half hour or so members of the group would come up and tease me and play with me, the only rule was they could not let_make me cum. Over all about 8-10 touched me (some multiple times) throughout the encounter. Idk if it was the viagra or that I broke a embarrassment limit, but at the end of the 30 minutes I told them to keep going. I stayed up there for nearly an hour letting the group enjoy me (and I was the youngest guy so the comments I got were a mix of teasing and encouragement). The part that got me the most aroused was hearing some of the couples getting it on. After an hour I ready to get off the table (only because I was getting sore from kneeling on the table). And yes when I got off the table I was permitted to cum.... and it was the most exciting orgasm of my life.

Like I said this was an amazing experience which broke me out of my super shy shell. And while I didn't go to major details. If the ladies of reddit want to ask any questions, I will entertain them

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8 months ago