We swapped couples a few times, and Linda looked smashing. I told her that her dress looked amazing, and she teased me that the next time she would wear a white dress for me would be at our wedding. I told her that I was looking forward to that day.Holly was in a black gown with red trim, that matched the cummerbund that Jack was wearing. And she was also having a great time, and looking forward to the evening. She was also nervous that she was leaving for college in a few months. Her acceptance letter had arrived the week before, and she had confirmation on her two scholarships including one for dance, thanks to her taking part in the flag team.Towards the end of the night, a slightly nervous Keith came up to our table. I hardly recognized him at first, his long hair was gone and it was now not even reaching his collar. He had arrived with Janice, a Junior we knew slightly as his date. He came up and asked if Holly would take a dance with him. She smiled and placed her hand on the. Joy get off of me and goes to her purse and asks if we can try something new and she pulls out a butt plug. This is a dream to take a MILFs anal virginity. So she gets on the bed and I lube up her plug. She is on her knees while laying her head on the bed, I move to one side of her and start teasing her asshole with the plug while rubbing her pussy. Her ass is very tight but I can tell she really wants it. I keep playing her pussy while going deeper and deeper with her plug until it finally slides all the way in. I keep playing with her plug feeling her ass opening more and more. She finally says shes ready for my cock, I get behind and lube her hole again. I slowly start sliding my cock her tight ass until its finally all the way in. I ask her how shes doing and says she didnt expect it to feel so good and hurt at the same time. She starts moving slowly up and down my cock moaning with every inch. I finally start thrusting into her and she lets out a moan of pleasure. I get to going.
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