I enjoy the drinking gambling and if some pussy falls in my lap I will fuck it. This story happened to me 20+ years ago.One time at the blackjack table I fire up this convo with this hot red head. She must have been in her mid 40s, me in my early 20s. After several hours of play and several drinks we both find out we are there alone. At one point she makes a large bet, 500 bucks I think. I tell her if she wins I will make the same bet next round. As she's dealt a black jack I'm thinking ok I'm all in with my 400 bucks. I move my chips in and she says if you loose you can take me to my room, that way loosing wont feel so bad. Well I hit my hand till I bust, with a laugh she knew I did that on purpose.We get to her room and I sit in the chair. She immediately gets on her knees between my legs and starts massaging my cock. As I lean back my rod is wanting out of my pants. She is trying to get my pants undone and I cant wait so I stand up undo my belt, unzip and pull my pants down to. Why are you being like this she meekly asked ? He replied he should have been like this ages ago.Stay like that he commanded.As she was leaning on his desk with her hands he rucked her dress right up over her back.She was scared but yet even more turned on.He admired the view of her from behind,the stockings,heels and the black pants dissecting her arse in to two smooth mounds of flesh.He was erect and she was wet at him viewing her like this and him basically dominating her.She turned round to speak and he told her to resume the position as hed heard enough lately.It was now his time,he said !!! He started to stroke one of her buttocks and she tensed but he just frimly pushed one leg further apart from the other.He not too gently stroked her labia right through her flimsy pants and he could feel heat and dampness.She squirmed and he shouted,im supposed to be humiliating you not giving you enjoyment.He lat fly at a buttock with one hand and again and again.She pleaded .Okay he said.
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