Down near Wall street about 2 years ago, late night, celebrating a friend’s promotion at an investment firm. Some fancy gala type thing nearby just let out, and some of them invaded the little pub we were in. Men in tuxedos, women all dressed in high end designer outfits and $1,000 heels. My buddy James (not the guy whose party it was) and I end up talking to two of the women who were clearly there after the event next door, without dates. Both in their mid-40’s, corporate V.P.’s or such. I tend to roll my eyes at the “resume and credentials” chit chat that usually happens in these crowds, but this was nothing of the sort, but rather it was flirty and aggressive by the ladies from the start. Jill is the one next to me, clearly on purpose based on how they slowly eyed us over and then approached. Tall, in shape, toned but not super skinny. Long jet black hair, tight and short red dress, studded Louboutins, oozing sexuality, already very drunk. After some banter among us 4, she’s touching me up and down my chest and legs under the bar, and daring me to do some shots, with all sorts of dirty wagers offered in a not so quiet whisper in my ear. I warn her that I’ve never lost a challenge like that, and she’s bound to regret it. After 4 tequilas and a Jameson chaser, she happily admits defeat, barely coherent, hands on my crotch above my pants, digging under my belt for more, mumbling in between drunken laughter that she wishes she could have me right there. I offer the bathroom, and we head that way. Small bar, long line. Major problem.
Author: NYCplayboy
Downtown debauchery: Anal in the alleyway
Down near Wall street about 2 years ago, late night, celebrating a friend’s promotion at an investment firm. Some fancy gala type thing nearby just let out, and some of them invaded the little pub we were in. Men in tuxedos, women all dressed in high end designer outfits and $1,000 heels. My buddy James (not the guy whose party it was) and I end up talking to two of the women who were clearly there after the event next door, without dates. Both in their mid-40’s, corporate V.P.’s or such. I tend to roll my eyes at the “resume and credentials” chit chat that usually happens in these crowds, but this was nothing of the sort, but rather it was flirty and aggressive by the ladies from the start. Jill is the one next to me, clearly on purpose based on how they slowly eyed us over and then approached. Tall, in shape, toned but not super skinny. Long jet black hair, tight and short red dress, studded Louboutins, oozing sexuality, already very drunk. After some banter among us 4, she’s touching me up and down my chest and legs under the bar, and daring me to do some shots, with all sorts of dirty wagers offered in a not so quiet whisper in my ear. I warn her that I’ve never lost a challenge like that, and she’s bound to regret it. After 4 tequilas and a Jameson chaser, she happily admits defeat, barely coherent, hands on my crotch above my pants, digging under my belt for more, mumbling in between drunken laughter that she wishes she could have me right there. I offer the bathroom, and we head that way. Small bar, long line. Major problem.