Young Woman with Older Man Ch. 04

Can I sleep with you?

Can I sleep with you? Am I dreaming? Did Lynn, the woman of my dreams, just ask me, the old perverted guy, if she could sleep with me?

Always breaking an uncomfortable moment with humor and always ruining my chance with a beautiful woman by saying the wrong thing, at the wrong time, a freight train of thoughts ran through my mind. Sometimes humor works, but most times it doesn't. Probably, it would more work for me, if I looked more like George Clooney and/or had his money. Only, I was a middle aged man with a head over heels attraction for a beautiful woman half my age.

No, Lynn, it's very inappropriate for you to sleep with me. How dare you ask me that? What is wrong with you? I'm old enough to be your father. You ought to be ashamed of yourself to want to put me in such a awkward and compromising position. How could you, a guest in my home, insult me by asking me a question like that?

Go away. I'm too upset to even talk to you. Get out! Get out of my room immediately. I can't stand to look at you, I'm so deeply offended. Please, return to your room, before I throw you out of my house and into the night the night to fend for yourself against, nocturnal creatures of all kinds.

As ridiculous as was her question, the retorts that I thought but, thankfully didn't verbalize, was just as ridiculous. Then, I wondered, what did she mean by wanting to know if she could sleep with me? Did she want to sleep or did she want to have sex?

"Yes, of course, you can sleep with me," as if she had just asked me, if I wanted a million dollars that she had found in her purse. Sleeping with her was like winning the lottery, anyway.

I moved to the side to make room for her, when what I really wanted to do was to move closer to the middle of the bed, so that she'd be butting up against me. When she passed by the moonlight that glowed through the open window, it revealed her shapely silhouette proving my suspicion that she was naked. Be still my heart. She's naked. Lynn, the woman of my dreams, is naked, in my room, and about to sleep with me in my bed. Thank you, Jesus!

Being that I was already in the room, when she entered, my eyes had already adjusted to the darkness and I could make out more of her voluptuous body, as she climbed in bed beside me. My heart and pulse raced to beat one another in my desire for her. It was times like this that I wish I had a crash cart or a nitroglycerine tablet in case I had a heart attack. Code blue! Realistically, I wish I had taken a Viagra. Still, with her walking by the window like that, I didn't need a Viagra because I already had a solid erection.

It was all so surreal and I couldn't have imagined a better dream than the one that was happening now in real life. Earlier that day, we were out walking our dogs in the dog park and I was happy just to be in her company, even for only an hour and now, here she is in my bedroom and in my bed naked. Generally, after I'm out with her walking through the dog park, that night, just before retiring to bed, I masturbate, while thinking about her. If I had fantasized this scenario, I never would have believed it. I never would have believed that this lovely and sexy 25-year-old woman would want to be with this lonely and horny 50-year-old man. Something like this never happens to someone like me.

She got in bed beside me and even without touching me, I could feel the heat of her body. She was hot. She was so very hot. I wanted to touch her and to feel her everywhere. I wished that I could hold her in my arms and kiss her. Just with the thought of her with me, my cock grew without the touch of my hand, until it stood straight out and up. Even though I was sexually excited, I was embarrassed and thought about turning away from her, so that she wouldn't see my erection. Now, I knew the answer to both of the previous questions, when wondering about her. She sleeps in the nude and she prefers the left side of the bed.

"I hope you understand and won't be offended that I don't want sex," she said with a pause. "That is not to say that I'm not attracted to you."

"It's okay. Don't worry about it," I whispered. Now embarrassed again, I figured she saw my erection.

Truly, it did not matter. Of course, I would have preferred an intimate, sexual relationship with her, but a platonic relationship, one where we sleep together in the nude, will certainly do just fine. I couldn't wait for the morning light to see her lying beside me naked. I wondered if she'd mind, if I took a few candid photos of her.

"It's just that I only need comfort and, well, you've been so nice to me by allowing me to stay in your beautiful home, and suddenly, I feel so close to you, closer than I ever have with my boyfriend or with any man," she said pausing again. "And you make me laugh. Some of the things that you say are so funny," she said laughing, no doubt thinking of some of the funny things that I had said. She paused again and I could feel that she had more to say, so I didn't respond. "I like you, Freddie. I really like you. You have been so very nice to me and never have you taken advantage of me, even with me lying beside you naked. I feel safe with you. I never felt safe with my boyfriend." I felt her exhale a relaxed breath. "I know you'd never take advantage of me for sex."

Damn, what do I have sucker written on my forehead? Does she think me a eunuch? I didn't know how to respond to her. I stayed quiet for a moment digesting what she said. Suddenly, she made me wish that I wasn't naked. She made me wish that I was wearing underwear and was not lying there with an erection. Now, I felt that I had betrayed her trust. I felt like a pervert. I felt like the wretched lecher that I was. I could feel my erection softening.

"Sex? Yes, of course, I understand. Please, don't worry about that. Sex never left, um crossed my mind," I said and we both laughed.

"Only, if you don't mind, Freddie, can you hold me? I can't fall asleep without being held, first."

Can I hold her? Is she kidding me? This just gets better and better. She's asking a horny, naked, middle aged man to hold her young, naked, sexy body against my decrepit, wrinkled, naked body. My mind was racing with imagined images of me having sex with her.

"I'd love to hold you, Lynn," I said wanting to finish it with...forever. "Only," I said with a pause, "I'm naked."

"That's okay. I'm naked, too."

I opened my arm and she snuggled beside me laying her hand on my hairy chest. The heat from her hand made my penis pulsate. From what I could feel of her without touching her, she felt incredible. I focused on the part of my body that touched her body trying to discern the shaped of her breasts by the sensation of them against my ribs. It was then that I wished I was built like a spider with 8 legs, or in my case, 8 arms with 8 hands.

The feel of her naked tits pressed against my ribs made me want to reach down and cup them. It was torture and she was driving me mad with sexual desire for her. This cuddling without touching was tortuous and felt too much like a couple's sex therapy class. Holding her like this, without touching her, was so erotic and so frustrating at the same time. Her patch of pubic hair tickled the hairs on my thigh and I so wanted to reach down and finger her. Afraid to touch her, afraid she'd get the wrong impression, and I'd touch something that I couldn't resist not touching, I stayed there with my hands out and my fingers splayed. Going for broke, rolling the dice, and taking the gamble, I asked her the question.

"Do you mind if I touch you? I don't mean in a sexual way but—"

"Touch me? Yes, of course, you may touch you, silly," she said laughing.

Slowly, softly, and gently, as if she was breakable, I ran my hand along her shoulders, down her back, and down to the top of her ass touching the top of her ass crack with the tips of my fingers. I so wanted to feel her firm ass, to cup her sweet bottom, to squeeze it, and to allow my fingers to probe her further between her legs. She has a wonderful ass and I've been lusting over her ass, since I first met her. I so wanted to feel her tits and to finger her pussy. I so wanted to make sweet, slow love to her. Only, one step at a time. She was already in my bedroom naked.

"I like that," she said. "That feels nice. You're touch is relaxing."

Great, I thought. Instead of turning her on, my touch is putting her to sleep.

I continued giving her a light back and shoulder massage with my hand traveling from her shoulders to her back and to just above her ass. Would you mind if I turned on the light? I never sleep in the dark; I wanted to say, but didn't. I laughed at the ridiculousness of the thought, while imagining her in an examination room with a 1,000 watt light bulb overhead illuminating her naked body.

Now, turn to the side and move your arms over your head. Now, lay on your back. Open your legs. Wider. Wider. Raise your knees. I was crazy with the thought of her posing in all kinds of positions. I thought about her boyfriend painting her in the nude. Boy, what a dope he was to lose his beauty.

She moved her hand across my chest with her fingers playing with my chest hairs. Her elbow came in contact with the tip of my now semi-erect penis and it suddenly sprung to life again with her accidental contact. My cock, not giving a care who, when, and where he fucked, tried to fuck her elbow.

"You have a nice, hard body," she said slowly running her hand over my chest, shoulders, biceps, and stomach. "I like a man with muscles. My boyfriend was a wimp. He had no muscles at all."

When she reached down and felt my stomach, my cock pulsated against her forearm. I was hoping that she'd reach her hand down just a little further. I wished I could feel what it was like to have her small, soft hand wrapped around my big, hard cock, as she stroked me. I wondered what it was like to have her mouth on my cock, as she blew me. I couldn't help but think about making sweet, slow love to her and then to pound her body with the lust of my desire.

"Well, you aren't so bad yourself. From what I have seen of you in the moonlight, you have a very shapely figure."

"Thank you." She moved her arm away and my stiff cock bounced off her elbow again. My cock was determined to fuck her elbow. "Sorry, I've given you an erection," she said with a giggle.

"It's okay. There'd be something seriously wrong with me, if I didn't have an erection with you lying beside me naked," I said laughing. "Being a heterosexual, horny man, I'm expected to become aroused, when a beautiful, naked woman crawls in bed with me to cuddle."

"Do you," she paused and it was a long pause that made me imagine every possible question that she was about to ask me, but never did I imagined her asking me this. "Do you want me to do something about that for you?"

"What do you mean?" As soon as I asked the question, I felt like the fool. I knew exactly what she meant.

Slowly, she moved her hand down my chest, along my stomach and touched my pubic hair with her fingertips, before reaching further down and taking my stiff cock in her hand. Her hand felt warm and soft, as if it belonged there. The excruciating length of time that it took her to slide her hand down from my chest to my cock was teasingly erotic. I think that I held my breath the whole time in sexual anticipation.

"I can relieve some of the stress of the day for you, if you'd like."

"What you are doing now feels wonderful," I said afraid to ask her to masturbate me. I mean, I haven't had a twenty-five-year-old give me hand job in twenty-five years.

Glad that she ignored my shy reticence, with that, she began slowly stroking me. The touch of her hand wrapped around my cock made me the hardest that I have been in years. She reached down and cupped my balls and then returned to holding and stroking my cock. She repeated the process several times. In the way that she fondled my cock and balls, it felt more like an erotic massage given to me from my personal, sex therapist than it did a sexual act. Lynn was giving me the best, slow hand job I have ever had in my life.

"Oh, Lynn, that feels incredible. Only, if you continue stroking me, you'll make me cum. I'm so very horny right now and have been ever since I met you."

There was a silence between us, but I could feel her thinking and knew she was about to ask me something.

"Have you thought about me," she said pausing, "naked?"

"Yes," I said instantly not even having to think about the answer.

"Have you imagined me touching you like this?" There was a slight quiver to her voice.

"Yes," I said suddenly feeling a bit awkwardly perverted.

"Did you ever masturbate," she said this time with a longer pause, "when thinking of me?" She asked in a breathless whisper.

"Lynn, I—"

"It's okay, you can tell me. I won't be offended. Matter of fact, communicating your sexual thoughts and desires excites me to know that you thought of being with me sexually, while masturbating to those thoughts." She laughed. "It's erotically intoxicating, when a woman knows that she drives her man wild with lustful desire for her.

I couldn't believe that she was getting turned on with this dirty pillow talk. I couldn't believe she called me 'her man'. Definitely, she was my kind of woman. Dirty pillow talk is paramount to putting me in the mood for hot sex. I just love a dirty girl, especially this pillow talking, dirty girl.

"Yes, I've masturbated, while thinking about being with you," I said glad that it was dark and she couldn't see me turning red and excited to be a participant in her pillow talk game. I felt foolish asking her the question, but I did. "Have you thought about me?" I said expecting her to laugh and to say, no.

"Yes, a few times, I wondered what it would be like to make love to you. I wondered what it would feel like to be in bed with you naked, as we are now, and with my hand around your cock as it is now."

"Did you ever masturbate when thinking about me?"

"Yes, I masturbated over the thought of you, after the first time we walked through the dog park. You were kind to me and made me laugh. That night, I touched myself with the thoughts of making love to you."

Oh, my God. She masturbated over me. I thought I was the only pervert to masturbate over anyone.

There was another silence as she continued slowly stroking my cock. Her hand felt amazing. She was so gentle and yet held it firm enough to give me the perfect tension. I could have not given myself a better hand job.

"What do you think about?"

"You know," I said, "the regular stuff." She continued stroking me only, now, a little faster, no doubt, either aroused that I masturbated over her or wanting to sexually excite me more with the hopes that I'd be more informative.

"Tell me. I want to know. I like this game," she said. "Did you think about making love to me? Did you think about eating my pussy? Did you think of me blowing you? Did you ever think of me sucking your cock? Did you imagine what it felt like to cum in my mouth?" She laughed. "Did you think of my tits and sucking my nipples?"

Oh, my God. Never have I been with a woman so forwardly sexual. The way she asked me those questions in rapid fire succession confessed that she was getting aroused, while giving me a hand job. Damn, as if sent from God, she was my Angel of sexual mercy. My kind of woman.

"Lynn, you are driving me nuts with all these questions." My cock was so hard and she was making me so horny with all this talk. "You're going to make me cum with all this hot, dirty talk."

"You don't like talking dirty during sex?"

Sex? Was that what we were having, after expressing telling me that she didn't want sex?

"Are you kidding me? I'm the master of dirty talk. I love talking dirty during sex. Only, you're going to make me cum," I said again.

"It's okay, Freddie, I want you to cum. That's the whole idea, after all, of relieving your stress."

She continued stroking me faster.

"Lynn," I said excitedly, "may I feel your body?"

"Yes, please, I want you to touch me, only not my pussy, not yet, not tonight." She laughed again. "I've been wondering when you were going to feel my tits and finger my nipples, only please don't suck them, not yet. I'm horny, too, you know, after stroking your cock while stroking your libido."

I thought that strange that she didn't want me to touch her pussy. I figured maybe she had her period or was getting her period or was not ready yet to take that step with me, an older man.

I reached down and felt her ass. I had been lusting over her ass. She had the best ass that my hand has ever felt. I loved feeling her ass. I couldn't get enough of touching her ass.

"You have an incredible ass, especially when it is highlighted in your tight jeans."

"So you like my ass, do you?" She laughed a melodious laugh. I loved her laugh and it was exciting to hear a woman laugh in my house again.

"No, I don't like your ass. I love your ass," I said with a laugh, while feeling the perfect round, firmness of her cheeks.

I reached my other hand over and across, and taking her breast in my hand, I fingered her nipple, while wishing that I could suck them. Her breast felt so soft, yet weighty and so very firm. Having been with women more my age, it had been many years, since I felt firm breast in my hand. All the women I've been with up to this point have been mature women, women who care more about their reading material than they do the condition of their bodies. Obviously, none of them had the supple body of a 25-year-old.

Even though she expressly told me not to suck them, I briefly touched her nipple. Her nipple was so very erect and they felt big between my fingers. I wished I could have seen what he breasts looked like. I wished I could have leaned down and taken her nipple in my mouth, but she had asked me not to do that, not yet, anyway. I so wanted to explore her pussy with my fingers, tongue, and cock.

"You have wonderful tits," I said. "The first time I saw your cleavage, was when your boyfriend tore open your dress. Seeing your bra, the top of your breasts, and your cleavage, made me so horny. You have that deep, natural line of cleavage that women pay plastic surgeons thousands of dollars to get."

"Do you really like my tits?" I watched the silhouette of her head look down at herself and I wondered how much she could see of me and of my cock.

"I love your tits."

"Touch my nipples," she said. "I know that I said for you not to go easy with my nipples but, I'm horny and I like having my nipples touched."

My fingers worked her nipples. Her nipples were so erect and her tits were big and firm. Fingering them, pulling them, turning them, and twisting them, I loved playing with her nipples. I couldn't wait for the morning light to show me her body. It took all the control that I had not to snap on the light.

"There's some tissue on the nightstand next to you," I said feeling the sensation that I was getting closer to shooting my load.

"Tissues? For what? I don't need to blow my nose," she said with a laugh.

"I'm getting ready to cum," I said, fearing that I'm make a sticky mess.

"I won't need any tissues, Freddie," she said sliding halfway down the length of me and taking me in her mouth.

To be continued...