Straight Male / 34
Extra Tips
When I was in college in Boston, I worked for a catering company that had a lot of wealthy clients. Three or four nights a week, I'd serve or tend bar in someone's home, usually surrounded by well-dressed and lovely women.
One night in Cambridge, I was packing up the van--being the closer paid more--and ended up having a chatting with Mrs. S (the hostess) as I ferried bins and boxes and crates. She asked if I wanted a beer before I left, and one thing led to another. I was 22, she was 48 and divorced, and we ended up having sex for most of the night. Standout memories include me eating her pussy while she perched on the granite countertop of her kitchen island, lounging on her leather sofa buck naked while she swallowed my cock, and filling her pussy with my cum as she bent over an ottoman in the same living room where I'd been serving her friends a few hours earlier. As I was leaving, she tucked an extra hundred dollars in my pocket with a smile and a kiss.
Three weeks later, I was packing up again after a dinner party for 8 women in Marblehead. Mrs. H, the hostess, lived in a great little house right on the waterfront. When I found her to say goodnight, she gave me a sassy grin and asked if I wanted a beer. I didn't think anything of it, but as we sipped, she mentioned that she was good friends with Mrs. S and that she was hoping for a little extra service before I left. Part of me was stunned at the secret getting out, but the rest was thrilled--Mrs. H was a slim brunette in her forties with small breasts tenting her silk blouse and long, slim legs.
Three hours later, we were lounging in her queen-sized bed overlooking the dark ocean. She smiled contentedly, her dark hair clinging to her forehead as she lay on her side and played with my chest hairs. "I haven't felt this good in years!" she murmured happily. I thought back over the preceding hours: taking her clothes off slowly and kissing every newly-exposed part of her skin; her riding me languidly, leaning down so I could bite her nipples; watching her slender hands milking my cock to explosion in the warmth of her mouth; and finally, just now, feeling her arms and legs wrapped tightly around me as I pounded down into her and emptied myself inside her.
"I was thinking the same!" I replied with a smile.
An hour later, $200 richer, I was unpacking the truck at the commercial kitchen, dog tired and happy.
Word got around a little more, and for the next year, I averaged two or three nights a month with an older woman. All in all, I earned an extra couple of thousand dollars. More importantly, I had a series of amazing sexual encounters with smart, beautiful, and eager women...every young man's dream!
One night in Cambridge, I was packing up the van--being the closer paid more--and ended up having a chatting with Mrs. S (the hostess) as I ferried bins and boxes and crates. She asked if I wanted a beer before I left, and one thing led to another. I was 22, she was 48 and divorced, and we ended up having sex for most of the night. Standout memories include me eating her pussy while she perched on the granite countertop of her kitchen island, lounging on her leather sofa buck naked while she swallowed my cock, and filling her pussy with my cum as she bent over an ottoman in the same living room where I'd been serving her friends a few hours earlier. As I was leaving, she tucked an extra hundred dollars in my pocket with a smile and a kiss.
Three weeks later, I was packing up again after a dinner party for 8 women in Marblehead. Mrs. H, the hostess, lived in a great little house right on the waterfront. When I found her to say goodnight, she gave me a sassy grin and asked if I wanted a beer. I didn't think anything of it, but as we sipped, she mentioned that she was good friends with Mrs. S and that she was hoping for a little extra service before I left. Part of me was stunned at the secret getting out, but the rest was thrilled--Mrs. H was a slim brunette in her forties with small breasts tenting her silk blouse and long, slim legs.
Three hours later, we were lounging in her queen-sized bed overlooking the dark ocean. She smiled contentedly, her dark hair clinging to her forehead as she lay on her side and played with my chest hairs. "I haven't felt this good in years!" she murmured happily. I thought back over the preceding hours: taking her clothes off slowly and kissing every newly-exposed part of her skin; her riding me languidly, leaning down so I could bite her nipples; watching her slender hands milking my cock to explosion in the warmth of her mouth; and finally, just now, feeling her arms and legs wrapped tightly around me as I pounded down into her and emptied myself inside her.
"I was thinking the same!" I replied with a smile.
An hour later, $200 richer, I was unpacking the truck at the commercial kitchen, dog tired and happy.
Word got around a little more, and for the next year, I averaged two or three nights a month with an older woman. All in all, I earned an extra couple of thousand dollars. More importantly, I had a series of amazing sexual encounters with smart, beautiful, and eager women...every young man's dream!
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