I usually publish in the Transgender & Crossdressers section but this story popped into my head and I had to get it down on (electronic) paper.
My name is Mason Ascher. I'm 47 years old and sleeping with my 19-year-old stepdaughter. Two years ago, you never could have convinced me something like this would happen.
I own my own business. I started it up right out of high school instead of going to college. There were some tough times at first, but I stuck with it and became very successful. I was now well off, not a millionaire by any means, but financially comfortable and headed in that direction.
I can still remember the moment like it was yesterday. I was only 29 at the time. Jane walked into my company looking for a job. She was only 18, she was carrying little 1 year old Janey on her hip. "I'm not looking for any handouts mister, I'll work hard for you. You'll get your money's worth, I promise!"
She explained she'd given birth to Janey when she was only 17. The biological father didn't want to have anything to do with being a parent and ran away, leaving her and the baby alone. Her parents were embarrassed and kicked her out of their house as soon as she turned 18. She'd been out on the streets for a couple of weeks now and was out of money and resources.
Something about her story resonated with me and I hired her on the spot. I started her at the lowest position in the company, but she was aggressive and smart. She worked her way up quickly, and within a year's time had already become an assistant manager. So far, hiring her had been a great decision.
Jane was very attractive, most of the guys in the company had asked her out but she always declined. She was 5' 4" tall, weighed 110 lbs. and was very toned. I found out later her measurements were 34C -- 24 -- 36. She had a rocking body! Her dark auburn hair was complemented by her emerald-green eyes, luscious pouty lips, and pert nose with just a light sprinkling of freckles.
We were having lunch in the break room one day. She was complaining, good naturedly, about all the guys in the company asking her out on dates. "Jane!" I said. "Why are you so surprised? You're a beautiful young woman; you're very successful here so far. Of course, these guys are going to ask you out. You're not telling me any of the guys are being over the top or too aggressive, are you? If so, I'll take you to Human Resources right away. You shouldn't have to put up with that from anyone!"
"No, no, it's not that. They've all been very nice and very respectful. It's just that there's only one guy in this company I'd be interested in dating, and he hasn't asked me out."
"Who is it? I can drop a hint to him for you, if you'd like me to."
She just stared at me until I became uncomfortable. She sighed and said, "It's you, you big dope! You've never seen me staring at you with big doe eyes? All the girls in the company have and tease me about it."
"Jane, no, I uh, no, I've never noticed. Jane I've always tried to be respectful to the women in this company. I would never want anyone to feel pressured like they had to go out on a date with the owner."
She smiled at me. "You're such a goof! But a kindhearted goof and a gentleman! So, what if I asked you out on a date? Would you go out with me?"
I thought about my so-called love life since I started the company. It was next to nonexistent. I had been so focused on building my business that I had let the personal side of my life go to hell. And here was this beautiful woman in front of me, practically telling me she had the hots for me and was asking me out on a date.
I decided quickly before she changed her mind. "Yes Jane, yes, I'll go out with you. It would be an honor and a privilege to go on a date with you."
She smiled from ear-to-ear. "Such a gentleman, so old-fashioned. Two of the many things that have attracted me to you!"
We made plans to go out for dinner and dancing that Saturday night. I picked her up at her apartment, Janey's babysitter was already there. Jane was a knockout. She was wearing a black silk ruched, backless halter dress that was tied behind her neck. It came to just below mid-thigh. She had on black nylons and black silk open-toe stilettos with 4" heels. She looked amazing.
"Wow, just wow! I feel underdressed." I was wearing a button shirt with blazer and dress slacks.
"You look fine, as a matter of fact, all the women in the restaurant are going to be jealous I'm with a hunk like you!"
I had made reservations at a small, upscale Italian restaurant. We had a small booth against the wall, so it was semi-private. Our dinner conversation was free and easy; we were able to talk about everything. I shared my struggles in building the business. Jane shared her personal struggles raising Janey as a teenage mother. The most difficult time had been when her parents kicked her out and told her they didn't want to see her again. She said she hadn't expected her parents to allow her to raise Janey in their house, she was just broken-hearted they didn't want to see her or their granddaughter again.
After the meal, we ordered our digestif and when the waiter brought Grappa for both of us, he also brought the check. Janey quickly reached out and grabbed the check. "What are you doing? I'm going to pay!"
"No, you are not!" She said it firmly and in such a way I knew she would take no argument from me. "I asked you out on this date and I am going to pay for dinner!"
I put my hands on top of hers. "On one condition."
"What's that?"
"Only if you let me pay the cover charge at the dance club and the drinks while we're inside."
She smiled at me, winked, and said, "I think I can go along with that. Now, I would like you to bring your Grappa over here and sit next to me until we get ready to go."