I met Marie the old-fashioned way. Drunk, at a bar. To be fair, I was drunk and she was sober, but still, my drunken state led me to hit on her, which made her shoot me down. I still entertained her enough to get her number, and after a few days of sober texting and calling, she finally agreed to go out with me.
We went out a few times and never progressed further than a good night kiss at the door. She was oddly reserved for a woman of her age (39), but definitely showed signs of passion in the few kisses we shared.
A little about me. I'm 44, in good shape, a little over 6', with a good job and a nice house. I was married in my late twenties for a few years and divorced ever since. I date a bit and usually end up in long term friends with benefits relationships with women around my age who aren't looking for anything serious.
The reason I hit on Marie in the first place is she was stunning. Around 5'6" and maybe 125 pounds, she had light blonde hair, high cheekbones, and glacial blue eyes. Basically she looked like a Norse goddess, and I would not have guessed she was a day over 30 when I approached her.
She was wearing jeans and a long-sleeved buttoned up shirt, and the lack of skin intrigued me in a bar full of women showing off ample assets. I could tell she had a nice body, but just how nice it might be kept me coming back for more.
She had me over for dinner two weeks into dating and we had wine with dinner. She loosened up and we ended up making out like teenagers on the couch.
"We need to talk," she said, after we came up for air.
"Oh, no!" I laughed. "Already?"
She swatted at my arm. "Nothing bad! It's just....it's really kind of hard to talk about is all."
She went on to tell me about her love history, and how she had never been married or even engaged. Her family was extremely religious, flirting with cult-like denominations, and that history had screwed her up for a long time.
"I was in therapy for years looking for answers that never were answered. In the last few years, I realized there really are no answers and I just need to live my life. The tough part is that I am attracted to you. Very attracted. I love kissing you and you make me want more."
"But?" I prompted.
"No buts, really. It's just, I've not had a very good track record when it comes to sex. I guess you could say I'm frigid. I've been with three men in my life and only a handful of times with each. I've probably had sex less than 20 times in my entire life."
I was shocked. By all accounts, I was sitting next to the nearest thing to a (almost) 40 year old virgin you could find. Add in that she was gorgeous, and my head spun even faster.
"I would never push you into anything," I said. "If you aren't comfortable with sex, I am fine with what we have."
She kissed me softly. "No, I want sex, I really do. I just don't want you to be disappointed."
"I could never be disappointed. The thing is, if we take that step, you have to trust me and let yourself go. Give yourself to me fully and I promise I can show you that you aren't frigid, and that you can enjoy sex as much as any woman."
"Give myself? What does that mean?"
"That sounds more ominous than it is. I just mean tell me your limits and trust me to stay within those limits. Everything within those limits, you have to follow my lead and just let go."
"Oh, okay. I read "50 Shades of Grey" and was wondering if this was one of those things," she laughed.
"Only if you want it to be."
"I'll pass. So, we going to do this now?"
She looked so adorable sitting there biting her lip, her cheeks flushed with embarrassment and a little arousal.
"No, not tonight. I think we should go away this weekend and start there. Can you get away?"
"Yes," she nodded.
We kissed a bit more and I tore myself away to drive home. My mind was racing at the thought of seducing this woman fully. I knew psychologically she might never enjoy sex, but in my heart knew I could bring her to embrace her physical side.
I started texting her the next day.
•What limits do you have?•
•Limits?•
•Oral sex? Giving and receiving•
•Definitely willing to try. No one has ever kissed me there before.•
•Positions? Up for anything?•
•Yes.•
•Any fantasies?•
•Maybe. Too shy right now. Let me get back to you on that one.•
Over the next few days I got a definite idea of her experience and desires. Her few fantasies she shared were very vanilla and involved heavy romance. I booked a nice suite at resort a couple hours away and did some shopping online and had my purchases overnighted.
I picked her up Friday after work and we drove to the resort. We ate at the restaurant and had a few drinks and basically loosened up a little. She was visibly nervous as I led her to the room. I led her inside and kissed her on the couch.
"Tonight, we aren't having sex," I said.
"Why?"
"Because tonight is just to get comfortable with each other and our bodies. Tomorrow, if everything goes good tonight, we will have the most amazing sex. Do you trust me?"
"Yes," she said shyly.
"Good. I am going to kiss you now, and as we kiss, I'm going to let my hands touch your body. Probably intimately. I will be taking your clothes off as well. Are you fine with that?"
"I think so," she said.
"If at any point I do anything that makes you uncomfortable, you have to tell me. You won't upset me."
"Okay."
I kissed her, softly, my tongue teasing her lips. I pulled her closer to me and let my hands rub her back and up her sides. Each time I would approach the side of her breasts, she would shudder a little, so I moved away and just rubbed her back slowly.
I kissed her more firmly, and she responded, letting me gently suck her tongue. This time, she pushed herself closer, and when I let my hands brush the sides of her breasts, she moaned softly instead of withdrawing.