I am Bobby a thirty-three year old bartender at a very nice hotel. I tend to hook up with older ladies for generous tips. This last one had turned into an affair she was paying my bills. I was on call and at her house four days a week and one them was an over night visit including breakfast. Sixty days in and it was working.
Carol was a forty-four-year-old divorced mother of one nineteen year old son and an alcoholic. She would suffer through the morning with her first drink not until three PM, and another every forty-five minutes after the previous drink. This should come out to five drinks every four hours. Then dinner at Seven and she rarely makes it pass ten-thirty.
Justin was nineteen into body building a high school grad, but not going to college. Hang out on the internet without a job momma pays for everything. I find his only fans page by mistake, gay for pay so it would seem. I start to question if he is into me.
Carol had passed out it was my off night from work and a sleepover with her. I hit the kitchen for a drink to find Justin in his underwear doing up his dishes.
Justin - Let me guess she's passed out again. Do you need help getting her in bed?
Me - No she is good, she's in her nightgown and everything.
Justin - You know you are not the first, right?
Me - I know, I'm not sure where this is going... but we're good. Aren't we? I ask.
Justin - You treat her better that most have. She loves to cuddle with you but how much is she paying you a month?
Me - Why are we going there?
Justin - I think it too much money, you should be doing us both for that price.
Me - I have never been with a guy and wouldn't know where to start.
Justin - You and my mother figured it out I am sure we could too. I play the girl you play the boy. How about a beer and a shot before we go to my bedroom bartender?
I did come down for a drink, and now I needed one. I open us up a beer and poured two shots explaining...
Me - I don't think I can go through with it. It's gay and you would have to be one hell of a kisser or I would have to be as drunk as your mother.
We tap shot glasses and drink. Each take a sip of beer. He comes over to me. Puts one hand on the back of my head lowering my mouth to his shoves his tongue in my mouth. I take his face in both of my hands. The hand on the back of my head pinches my right nipple while the other fondles my junk. I am instantly reminded I need to get off today I don't think I care if it's gay. I am getting too turned on.
We go up in his bedroom and both do some gay stuff for the first time. The mind blowing blow job leading to unbelievable butt sex. I was almost gay when we finished.
Then Justin said... I'm in love with you bro, that was wonderful. I had no idea that could be so good.
I am human I have feeling and I too was impressed with what just happened. But love? We laid there cuddling. He has had some limited experience with guys in high school and entertains much older men online but this what we did was real. He was just a great kisser for being a guy. We ended up falling a sleep together and doing it all over again the next morning. Before waking Carol up for breakfast with a kiss. That felt weird and i was so glad to go home. I was seriously thinking of calling it all off. Thanks to Carol I had money saved, and I earned enough could support myself twice over.
Carol and I didn't have a date for two days which also would mean Justin and I didn't either. I was trying to justify enjoying sex with Justin so much. I liked Carol and we had fun together, she was fun in bed. That fact was Justin was better at pleasing a man. I have had my job bartending for over five years. It is a prime shift, I own my condo I own my car. I have slept with over a hundred different females. Most of them affairs not one night stands. They end because we get caught, get too serious, the marriage talk, they find different or cheaper. I work a shift with Julie a thirty year old lesbian that hates that I can screw older woman for tips. She is into younger.
Me - I had sex with a guy last night for the first time.
Julie - Oh wow that's the last thing I expected from you. Well how did it go? Are you going back for seconds?
Me - Not sure, I feel weird about it. I didn't think I would like it so much. Damn he was good.
Julie - It's chemistry bro, great sex don't just happen. It takes two people. You just have not had hot sex for a while dating older females. Then she said... You should hit the gay bar with me after work. Check out what is out there.
Me - I think that's a great idea.
It was a great idea, and gay guys of all ages checked me out. A couple of muscle boys that reminded me of Justin were dancing on a stage. It all just seemed kind of normal just gay people. Guys hanging on guys and girls on girls on some far off distant planet. Not sure why but when I left the bar I knew I had to end things with Carol. I canceled our date for the following day. Justin texted me back saying his mother was in the hospital and to call him.
I did and left to meet him there. She was out of it, alcohol poisoning and a mix of medications she had zero idea who I was. But she did know her son was homosexual and telling everyone right in front of him.
Mom - Meet my homosexual son Justin. I'm sorry why are you here, do I know you?
Justin - Mom he is a friend of mind he comes over to our house all the time. It's Bobby.
Then she goes off on how her son is gay and could use a boyfriend like me. Justin gets weird as I talk like that's a possibility.
Me - I say we are friends and I think he's fantastic, and extremely good looking but I am too old for him.
Mom - He needs older.
Justin says our good nights as she is staying in the hospital and wants me to come over. I suggest we try something different and we go to my place. He was beaming at the opportunity. We left his car there and he came back to my place. After getting naked and in bed a serious conversation on what make sex so hot between us. A young male version of his mother was the best we could come up with. I touch and tasted male body parts for the first time ever. I more than anything want to make him squirm in pleasure.
I and Justin continued for hours taking turns getting each other off before we finally made love. One again he said I love you Bobby
Bobby (me) - I love you too Justin.
I feel tears fall silently and puddle on my chest as he holds on tight. An exhale and he looks up and asks how come you're so good at gay stuff is you have never done it before.
I blame it all on him for making me gay in the first place. He moves in with me and starts college the following year. Carol gets better but never remembers us dating, just Justin's boyfriend that she met in while the hospital. I start treating all my customers like a potential date male or female and my tips go through the roof. Older lonely guys like to flirt too, The manager of the hotel finds out I am gay with a younger boyfriend I am supporting through college. (Carol was paying for it.) Yet all these older female and male customers love me. He makes me asst. bar manager. Then someone listed it in a gay guide and things got a little weird every once in a while.
Into Temptation - Story Time Blog
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