Setting the timeline here. This is a few months after I masturbated while my bf’s roommate was secretly watching. I go into more detail here https://www.reddit.com/r/sexstories/s/1QkNUJWKBp

So a few months had passed and my bf’s roommate had became bolder now. For instance, He would walk in while I was changing and not look away. His hugs became more touchy and so on. Lol I asked him to buy me some tampons once. So he was feeling closer/bolder as well. I was enjoying it too. It was super hot to tease him.

One day, I was again masturbating on the couch while he was around and he calls across the room ‘you know I can see AND hear you right?’ I retort back, ‘do you think that’s by accident?’ And I start laughing.

He becomes serious, walks over to the couch. I cover myself a bit.

He says, ‘let’s have a bet, if I win, you will let me finger you to orgasm and if I lose, I will be your errand boy for a month’

I laugh and say ‘are you crazy no ways’ But my heart is racing. He tries to convince me for a bit and gives up. But my heart is racing still thinking about it.

Few weeks go by and we start arguing about men’s vs women’s tennis. Both of us are tennis buffs and play at a high level.

He suddenly grins and says, ‘ I bet I can beat you’. I say, no ways. He pushes for a bet again and I accept the challenge without thinking. He then reminds me of our conversation and says ‘if you lose, I finger you and if you win, I will be your errand boy for a month and you can’t back out now’

Shoot what have I done, I thought to myself. But I was sure I could beat him.

We go to the courts the next day and he suggests a 10 point tie break. Ignoring my better judgement, I agree. Tie breaks are risky. He is much taller and has a big serve which puts him at an advantage in a tie break. In a full match, I will have more chances.

Anyways, we play the tie break. He wins comfortably and I am flushed. He laughs and comes running over excited. I am now stammering as I try to back off from the deal. He wouldn’t budge.

I try to negotiate, we go back and forth for sometime. We finally agree that 1. I will give him 3 lap dances completely nude. I can wear a short skirt and a bra but no underwear. 2. It should last for 5 mins. 3. He would only wear an underwear

We shower, go back and he gets ready to collect. All this while, my heart is racing. I am definitely excited but scared. Lol I had flashed at him so much. It almost felt this was bound to happen.

As I wear my short skirt which comes mid thigh, I am completely wet. I wear a lingerie bra, the only kinds I have and go to his room where he ready on the chair. He is grinning ear to ear.

I avoid any eye contact and sit on him. I can feel his penis against my bare bottom through his underwear. As I grind, I can feel his penis rub against my clit. I am too wet and realize he can feel it too. My wet pussy is making a mess on him. I am moaning slightly and try to stifle them.

Before I climax, I quickly get up give him an embarrassing smile and leave.