Last Chance at Forever Love Ch. 04

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Sophia sleeps with Jimmy and gives him sexy pillow talk.
8.8k words
4.73
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Part 3 of the 10 part series

Updated 06/09/2023
Created 11/30/2018
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Sophia sleeps with Jimmy

Continued from Chapter 03:

Her smile and her beautiful, brown eyes touched my heart and I so wanted to lean over and kiss her. Only, instead of instantly reacting to my sexual wants and lustful needs, I needed to fan her flames of sexual desire first. Somehow, with her so young and me so much older, I needed to make her want to kiss me. I didn't want to rush the fire by smothering the flames with my horniness. Yet, fortunately for me, she must have sensed the moment because she leaned over and kissed me.

'She kissed me. Sophia kissed me,' I thought with my heart swooning and my cock hardening.

Our first kiss, it was so surreal and I couldn't believe that she kissed me. It was a short kiss, a peck really, but it was on my lips. It was so quick that I didn't have a chance to react to it and to kiss her back. I didn't even have the chance to close my eyes. As if I was her college professor and she was my favorite student that I had given an 'A' to on the final exam, she caught me by surprise.

'Wow,' I thought. 'As if I don't have enough fodder to masturbate over her after seeing her in her ripped dress, her open bra, in her panties and bra, and now with her kissing me, I can't wait masturbate over her tonight.'

Our first kiss, the romantic that I am; I wished it had been longer with our naked bodies and tongues entwined in passion. I wished we were in a better setting than on my back porch, somewhere with a sunrise or a sunset, perhaps, by the ocean, or atop a mountain, or in the valley by a scenic stream. Still, I was ecstatic for her sudden and unexpected display of affection.

Later that night, as I drifted off to sleep thinking about her sleeping in the guest bedroom, my hand found my cock and I began to slowly stroke myself to a nice erection. She had made me horny all day, especially when she changed her clothes in front of me and especially when she turned to face me in her bra and panties. Unable to stop myself from staring at her bra clad breasts and her panty clad pussy, she has a wonderfully sexy body, the best body these old eyes have ever seen in a long while.

I thought about her kissing me. I thought about returning her kiss. I imagined parting her lips with my tongue and French kissing her. I wondered if she stayed, if we'd kiss one another in the morning and again at night. I wondered if she stayed, if eventually we'd do more than just kissing one another good morning and goodnight. I wondered if she stayed, if we'd ever have sex. Only, too much to hope for too soon, I needed to bide my time. I needed to take it slow. She was here to sleep. She wasn't here for sex.

Nonetheless, even after cautioning myself to take it slow, I thought about kissing her while feeling her through her clothes. I thought about kissing her while slowly undressing her. Then, once she was finally naked, so that I could revel in the beauty of her naked body, I'd ask her to turn from side to side. I thought about her standing before me in her bra and panties, as she did earlier. I thought about her in those skin, tight blue jeans. I thought about her topless before I thought about her naked.

She was so beautiful. She was so sexy. Now, that she was here in my house, this was my chance to take our friendship to the next level. This was my chance to somehow make her want me. This was my chance to sexually seduce her and make her mine.

# # #

Normally, I don't sleep in the nude, but tonight it was hot and humid and I was horny. Since I'm not a big fan of air conditioning, unless I really had to waste electricity to cool the house down, I run the overhead fans with the windows and my bedroom door wide open for the cross breeze. Still, even with that, it was uncomfortably warm.

I wondered if she was hot. With her confessing that she could have been a nudist, I wondered if she slept in the nude. With her so sexy, I wondered if she was horny. I wondered if I should switch on the air conditioning for her comfort. In the way that I slept with my bedroom door open, I wondered if she slept with the bedroom door open. I wondered if she slept with the light on, with the bedroom door open, and in the nude.

'Holy Hell,' I thought.

Suddenly, I imagined her naked. I imagined her sleeping with the light on and her door wide open. Worth a shot, I thought about walking down the hall on the pretense of rechecking and securing the house for the night to see what I could see of her.

I hoped to catch her lying on her bed asleep naked and with the light on. Figuring, no doubt, that if I saw her lying there naked that I'd be unable to control myself from staring at her naked body and/or touching her naked body while she lay sleeping, I thought better of it. With our newly formed relationship blossoming so well, I didn't want to prematurely ruin things between us by rushing something that she may not want.

Slow and smooth is better than fast and rushed. The last thing that I wanted to do was to scare her. The last thing that I wanted to do was to make her unduly uncomfortable. The last thing that I wanted to do was to make her leave and flee my house in the middle of the night for fear that I'd rape her.

Slowly stroking myself, instead, I figured that I'd just masturbate my horniness for her in a tissue. Then, when I looked up, as if I was dreaming or imagining her, she was standing in my bedroom doorway clutching the length of her oversized pillow against her beautiful body. Quickly, not wanting her to catch me masturbating while hoping that she couldn't see my stiff prick in the dark, I moved my hand away from my cock.

"I can't sleep," she said pausing before confessing her reason why she couldn't sleep. "It's been a long while since I slept alone," she said yawning.

'Someone so beautiful and so sexy should never sleep alone,' I thought.

I wondered if she was expecting me to invite her to sleep with me? Only, even though I'd love nothing more than for her to sleep with me, in my dreams, I didn't dare ask her to sleep with me. Not wanting to come across as the lecherous, older man that I was, how could I face her tomorrow if she said no and rejected my offer to share my bed. There was a long pause and, not thinking that she'd want to sleep with me, she stunned me with what she said next.

"May I sleep with you?"

'Wait? What? What did she just say? Did she if she could sleep with me,' I thought while trying to figure out if I was dreaming or sexually fantasizing her standing there?

Her words echoed in my mind. She asked if she can sleep with me. She wanted to sleep in my bed with me. This day just gets better.

She stood in my bedroom doorway clutching her king-sized pillow that covered all of her body except for her legs and her forearms. I wondered what she was wearing under the pillow. I wondered what she wore to bed. I imagined her wearing a short, sheer, low-cut, and sexy nightgown. Then, when she turned more to the side and I saw her naked ass, I was shocked yet sexually excited that she was naked.

'Sophia is naked,' I thought while trying to wrap my horny brain around her being naked and wanting to sleep with me. 'She's not wearing a nightgown. She's not even wearing panties. She's not wearing any clothes. She's naked. Sophia is naked and wants to sleep with me.'

Unable to wrap my horny brain around her seemingly innocent question, I didn't react in time.

"May I sleep with you," she asked again?

Now that she asked if she could sleep with me in my bed, I was baffled. This young woman I met in the dog park a few months ago was here in my house asking if she could sleep with me. Now that she was here, there was so much I didn't know about her and so much that I needed to know, the little things that suddenly become so important, when they're missing from your daily routine.

What does she eat for breakfast? What time does she go to bed? What time does she get up in the morning? What does she look like in the morning without makeup?

There were so many things to learn about her. Which programs does she watch on television? Does she like watching baseball? What about football? She's tall. Does she watch basketball? Maybe once an ice-skater, she enjoys watching hockey; lots of women do. It was then that I realized that I needed to get a life instead of living my live vicariously through the lives of professional sports teams and their athletes.

What seemed like minutes were only a few seconds. My quandary about her private life continued in my mind. What kind of music does she like? Which side of the bed does she prefer? Does she sleep in pajamas, a nightgown, or in the nude? I could only imagine the image of her sleeping in the nude. Okay, the last three questions, I admit, does she wear pajamas, a nightgown, or sleep in the nude, were unnecessary as she was already standing there naked now.

Later, as things came up in our conversations, I'd make special notes of her preferences. Yet, for now, deliberately exposing my erection to her, albeit in the dark, I moved my hand away from my naked prick. I slid over to the other side, patted my side of the bed, and invited her to sleep with me.

Chapter 04:

'May I sleep with you? May I sleep with you?' Her voice echoed in my mind. 'Am I dreaming,' I thought?

Playing over again in my mind, did Sophia, the woman of my dreams, just ask me, the old perverted guy, if she could sleep with me? Yet, here she was naked and in bed beside me. Wondering again if I was dreaming, I was tempted to touch her to see if she was real.

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 to a beautiful woman half my age.

'What should I say? What should I do? What's the next step in trying to sexually seduce a beautiful, naked women who's half my age sleeping with me,' I wondered?

Normally with her already in bed with me naked, I'd think my work was done. Yet, she was from a different generation. She was like bedding one of my daughters and they speak a language that I don't understand. Nonetheless, I imagined different scenarios.

'No, Sophia, sorry but it's very inappropriate for you to sleep with me, especially with you naked. 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 an awkward and compromising position. How could you, a guest in my home, insult me by asking me if you can sleep with me,' I imagined saying? 'What kind of man do you take me for?'

'Go away,' I imagined saying to her while continuing my internal dialogue. 'I'm too upset to even talk to you. Get out! Get out of my bed and 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 the wild, nocturnal creatures.'

As ridiculous as was her question, the retorts that I thought but, thankfully didn't verbalize, were just as ridiculous. Who was I kidding? I wanted her to sleep with me, especially with her already naked. 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? I needed a generation gap translator. I wondered if Amazon sold them online.

"Yes, of course, you may sleep with me."

Her asking to sleep with me was as if she had just asked me, if I wanted to share a winning multi-million-dollar lottery ticket that she had found in her purse. Sleeping with her was like winning the lottery. Other than winning the lottery, I couldn't think of anything better than to sleep with her, that is other than winning the lottery and sleeping with her.

I moved further 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. Sophia, the woman of my dreams, is naked, in my room, and about to sleep with me in my bed. Thank you, Jesus!

Since 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! He's overly, sexually excited.'

Realistically, I wish I had taken a Viagra or a Cialis in advance. Yet, I had no idea that she'd want to sleep with me. Yet, no matter, with her asking if she could sleep with me and walking by the window like that, I didn't need a Viagra or a Cialis because I already had a solid erection.

With her posing that sexy, sexual question to me, 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, when we were out walking our dogs in the dog park, I was happy just to be in her company. To be with her even for only an hour and, now, here she was 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 imagining her naked and having sex with 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. Unless I was rich, powerful, and/or famous, 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. Literally and figuratively, she was so very hot. I wanted to touch her and feel her everywhere. I wished I could hold her in my arms, kiss her, tell her that I love her, and want to marry her. Yet, the best way for her to leave was for me to make an ass of myself by confessing my love and proposing marriage.

Just with the thought of her with me in my bed now, my cock grew without the touch of my hand, until it stood straight up. Even though I was sexually excited, I was embarrassed. Old enough to be her father, she was young enough to be my daughter. If my twin daughters knew that I was sleeping with a woman their age, they'd be disappointed in me.

I thought about turning away from her, so that she wouldn't see my erection. Yet, I wanted her to see my erection. I wanted to see her reaction to seeing my stiff prick. Moreover, I wanted her to see that sexual lust that I had for her. At least now, I knew the answer to two of my questions. 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. As if she had thrown cold water on my erection, I was as confused as I was disappointed. "That's not to say that I'm not sexually attracted to you. I am," she confessed.

I was confused.

'If she didn't want sex,' I thought. 'Then, why did she come to my room naked?'

If such a guide exists, I really needed that generation gap translator to understand if she wanted sex or didn't want sex.

'She doesn't want sex but she's sexually attracted to me,' I thought. 'Okay, that's a good start. I can work with that.'

"It's okay. Don't worry about it," I whispered. "I wasn't expecting sex," I said lying.

Now embarrassed again, I figured she saw my erection. I figured she knew that I was sexually excited. Yet, it didn't matter. In the way that she exposed her naked body to me, I was eager to expose my naked cock to her.

Of course, I would have preferred an intimate, sexual relationship with her. I would have preferred her to allow me to touch and feel her everywhere. I would have preferred she would have made me cum after I made her cum. Yet, a platonic relationship, one where we sleep together in the nude, will do just fine.

I couldn't wait for the morning light to see her lying beside me naked. Friends with benefits, I wondered if she'd mind if I touched her and felt her as she slept. Something to show all of my friends when bragging to them that I slept with a beautiful, sexy, and shapely, 25-year-old woman, I wondered if she'd mind if I took a few candid photos of her in the morning. Yet, chances are, just my luck, she'd be covered head to toe with the sheet.

"It's just that I can't sleep alone and only wanted the comfort of having someone beside me as I slept," she said.

'Someone? She'd readily chose anyone to sleep beside her? I wish I knew that before. Yet, why not sleep with her dog,' I thought?

Yet, instead of talking, instead of saying the wrong thing at the wrong time, something I routinely do, I listened.

# # #

"You've been so nice to me by allowing me to stay in your beautiful home. Because of our friendship, I suddenly feel so close to you, closer than I ever have with my boyfriend or with any man," she said pausing again.

I smiled with the knowledge that she felt close to me. Yet, unable to shake the thought from my horny mind, I wondered about friends with benefits. I wondered what benefits I'd be entitled to as her friend. Not sure what that really was, I wondered if it came with an instruction manual and a laminated card like the one that I have with AAA and AARP. Perhaps, I could only look but not touch.

"I feel close to you, too, Sophia," literally and figuratively, I wanted to say but, not wanting to ruin the moment, I didn't say what I was thinking.

Instead, with us having missed our time talking while walking through the dog park today, because of us being interrupted by her boyfriend, now ex-boyfriend, I just allowed her to continue talking.

"You make me laugh. Some of the things that you say are so funny," she said laughing, no doubt while 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, Jimmy. I really like you. You have been so very nice to me and never have you tried to take sexual 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,' I thought? 'Does she think me a eunuch? Didn't she see my erection?'

Other than to remain quiet, I didn't know how to respond to her. Instead of opening my mouth and inserting my foot, I digested all that she had said. Suddenly, embarrassed, 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 the pervert that I am. I felt like the wretched lecher that I was. Suddenly, ashamed, I could feel my erection softening.

# # #

"Sex? Yes, of course, I understand. Please, don't worry about that," I said as if I was her father sleeping with his daughter. Sex never left, um, I mean, crossed my mind," I said and we both laughed.

Then, she fell quiet and I could literally feel her thinking. Obviously, struggling with her thoughts and, perhaps, rethinking what she was going to say, she uttered it anyway.

"As long as you don't mind, only if you want to, I don't mind if you hold me," she said.

She turned her head to look at me in the moonlight. My dream woman, she was so beautiful. My sexual fantasy woman, she was so sexy. Then, when I took too long to respond, she asked me again.