7 years
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I need advice. My boyfriend and I recently did something and I’m very conflicted about it. First of all, I have never done anything like this before. Second, it is not something that I dreamed about or even fantasized about. And, most of all, I am a one man woman. I have no desires for threesomes or swinging, or anything like that.

Okay, now that is out of the way, I met my boyfriend for a late dinner at a nice Italian restaurant. We left a little before 11pm and were saying good night in the parking lot and making out. Playfully he removed my top. The bus boys came out and were doing some work in the back of the restaurant. He shielded me and I covered myself with my arms.

Of course, they noticed and they were good about it and were giggling at us. Then, out of no where my boyfriend motioned for them to come over. It was obvious they wanted to see and I was very shy and hesitant. My boyfriend gently pulled my arms down and I used that as an excuse to expose myself. They made comments that were very complimentary and I got dressed.

The advice I need is to know if this type of behavior is abhorrent? I’m very torn over the events of that evening. Was my boyfriend disrespectful? Was I acting like a floozy? Am I immoral because I thought it was fun? If I never did this again, I’d be okay with it. Does that make me a prude?

My boyfriend thinks I am over analyzing it and it was a lark.

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When I was younger, about 16, I was insatiable and as a result of having my first anonymous hookup with another kid that was 16 (off omegle of all things) I sought to have more.
In this effort I downloaded Grindr and lied about being 18, eventually finding someone who hosted an anon darkroom not even 5 minutes away and who was more than happy leaving their door unlocked and a** ready. After I was invited over and tentatively entered their place I immediately set about u*********, going to nothing in a minute and slowly started up the steps to his room. Once in his room I was approached in the dark by him – a 30-something yr old man who was equally as naked but twice my size – and he reached down and started to blow me once he settled on his knees. Within minutes once I was sufficiently erect I prodded him onto the bed and had him bend over, eventually sliding in without any additional lubrication and begun to – at the age of 16 – f*** this older mans a**. I went for about 20 minutes by my estimation and slowly over the course of the f****** went from doggy, to sideways to having him lie fully down whilst I went to town on him.
Eventually I finished in him and got up and left. Once home I gushed to him about how much fun it was and how I appreciated him taking a chance with me, with some more conversation eventually leading to my age being revealed and – to my own surprise – him revealing that he’d prefer it if we kept going in spite of it. I’d meet him continuously, probably once to 3 times a month or even multiple times in the same week until I moved away at 18. I never saw his face but I remember being inside him so vividly.