Comforting My Step-daughter

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Restoring her sexual self esteem.
17k words
4.66
266.8k
165

Part 1 of the 6 part series

Updated 06/07/2023
Created 03/23/2012
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The following is a work of fiction. Copyright 2012 It builds a bit slowly, but I hope you find that the ending is worth the time to get there. As always, comments welcomed, and please vote (5's appreciated).

*

I am a 50+ widower. My second wife was killed in an auto accident by a drunk driver about three years after we had gotten married. That was four years ago, so I had pretty much gotten over it, and had moved on in my life. I did not have a new woman in my life, although I did have a couple of female friends with benefits. I also had Amy, my step-daughter. Amy was 10 when her mom and I had started dating. She was now in her mid 20's. She was the spitting image of her mom, at least of the pictures of her mom at the same age. She was petite, standing only about 5' tall and definitely on the curvy side, with a gorgeous butt, larger than average boobs, and a bit of a tummy. She was blonde with a smattering of freckles across her nose and cheeks, with hazel eyes.

Amy had married at 19, having gotten pregnant with her high school boyfriend, and her son was just starting in elementary school. I had never really liked her husband, but it was none of my business. So I had kept my mouth shut all along, even though I was convinced that he was abusing her; emotionally, if not physically. Since her mom had died, Amy and I got together about once every few weeks, sometimes including her son in a day out, and sometimes, just the two of us having dinner and a drink. Her husband tagged along once in awhile, but Amy preferred to have it just be the two of us. Her dad had disappeared out of her life before she was three, so I was her only parent; or pseudo parent.

It was a Friday in late in July when I received a text from her, asking if we could have dinner that evening. I had no plans other than working on one of my model locomotives, so, of course, I agreed. I suggested she meet me at one of our favorite restaurants, and then showered, and threw on my jeans and a sweatshirt, which were my normal casual wear. Ninety minutes later I was seated at a table awaiting her arrival. Fashionably late, she joined me, and I could tell instantly that she had been crying. I gave her the normal hug and we sat down. As much as I wanted to ask her what was going on, I bided my time, figuring that sooner or later she would share.

I'll note here that as Amy had grown up, we had gotten to the point where no subject was taboo. This was the result of her lesbian adventure as a senior in high school, when she had confided in me, and asked my help in telling her mother. Both her mom and I were open minded, and the conversation had gone a lot smoother than she had imagined, and from that time on, she talked with me about almost everything.

We chitchatted while we studied the menu, and she shared that David, her husband, had gone fishing for the weekend with their son. Clearly that wasn't the source of her unhappiness, as they did that regularly. I continued to listen as I ordered a nice steak, and she ordered a Cobb salad. I ordered a bottle of Merlot for us to share. She asked me how my novel was coming along, as I had retired the year before and had started trying to write the novel I had thought about for the last ten years. I shared my progress, very little, admitting that I was spending more time with my HO railroad than at my keyboard. Our food arrived, and after a few bites, I noticed that she had teared up again, but I remained silent, figuring she would share eventually.

"Dad, am I sexy?"

I about choked on my bite of steak, but quickly grasped that I was dealing with a young woman who had just had her sexual self esteem destroyed in one way or another. "Oh, sweetie," I responded, "You are quite a sexy young thing. Why do you ask?"

Her tears were flowing now. "Well, I found out today that David has been fucking Trina, the teeny-bopper that lives next door to us. When I confronted him with the facts, he didn't deny it. He just told me that I didn't turn him on anymore. I know I'm a bit overweight, and my boobs sag a bit. I guess I'm over the hill, huh?"

"Jesus, Amy. If you're over the hill, what does that make me? Dead?"

"You're not dead."

"There you go. You're not over the hill either. He's just an asshole. And besides, being sexy is an attitude more than how you look."

"Whaddya mean, an attitude?"

I had no clue where this conversation was headed, but I figured she needed to talk it out, so I went along. "Well, basically, as far as I'm concerned, I consider a woman sexy when she displays self confidence, dresses confidently, and is willing to engage sincerely with a member of the opposite sex about the excitement of life." I knew it sounded corny, but I didn't want to get too specific.

"I take it you thought mom was sexy?"

"Duh! I wouldn't have fallen in love with her and married her if she wasn't."

"And I guess you two had a pretty good sex life?"

"Uh, yeah. Why?"

"Well, I guess I'm trying to figure out what a normal sex life is."

"What do you mean?"

"Well, ever since David started working at his current job, we've had sex about once a month, and then only when he wants it. And, to be honest, it hasn't been very enjoyable."

"For you or for him?"

"Definitely not for me. As for him, well, it is pretty much he climbs in bed with me, spreads my legs, and rams his cock into me. And even before I've gotten into a rhythm, he ejaculates, pulls out, rolls over and goes to sleep."

"I can certainly understand how you wouldn't enjoy that. And personally, if that's all there was to sex, I wouldn't enjoy it all that much either."

Now, she questioned my response, "What do you mean; he ejaculated. Isn't that what it's about?"

"Oh, god, baby. Sex is a lot more than just ejaculating. That's certainly pleasurable, but I assure you there is a lot more to it than just that."

"Oh," was all she said, as she returned to eating her barely touched salad. I followed suit by slicing another bite of steak. For the next ten minutes or so, we ate in silence. I watched her as she ate, and assuming I could read her facial expressions, it was clear she was trying to grasp the meaning of our short conversation.

We finished our entrees, and both of us declined dessert, but we did each have a Grand Marnier. But, we drank the Marniers in silence. As I paid the bill with my credit card, Amy broke the silence by asking, "Dad, would it be okay if I spent the weekend with you?"

I hesitated, as that would be problematic for me. My friend Cindy was planning on visiting with me the following evening. We usually got together once every few weeks, got totally stoned, and watched some porn. Depending on our moods, we would fuck each other silly, or watch each other masturbate, or some combination thereof. I had been horny all week, and was really looking forward to the evening of total raunchy behavior. But, I also could tell that Amy needed some loving attention, and how could I deny her at her time of need.

My hesitation was obvious, and before I could speak, she jumped in with a follow-up, "Oh, gawd, I'm so sorry; you must have plans. I'll go home now."

I stammered for a moment, trying to find a good solution. Finally, I got it out. "Look, sweetie, why don't you come over and spend the night tonight, and we'll take it from there. I have no plans for the rest of the evening, and it's clear you need some company. The spare room is yours."

"Thanks, Daddy."

"Do you need to go home for clothes or anything?"

"No, 'cause I was hoping you'd say yes, so I threw a couple of things in my overnight bag. How 'bout let's go watch a movie together?"

"That'll work." And with that, we left our dinner table and headed the seven miles over to my condo.

We got to my condo, and as we entered I told her I was going to get more comfortable. She quickly agreed and disappeared off to my spare bedroom. I changed into my lounging pants and a loose t-shirt, and headed to the kitchen to open another bottle of wine. Both of us were barely on the legal side of sobriety, but since we were now in for the night, it didn't matter. I had just popped the cork and poured us two glasses of wine when Amy walked in to join me. I did my best not to stare, but if weren't my step-daughter, I would have. She had put on a pair of quite short boxer shorts and a crop tee. It was quite evident that she was not wearing a bra, and her nipples were blatantly pushing the material of her tee out. The tee was cropped so short that as she moved, the underside of her breasts would be exposed ever so slightly.

"Jeez," I said, "that may be a bit too casual."

"What's wrong with this? It's just you and me."

"Mmmm, yow. But I'm still a male, and your step dad. Your outfit is just a bit too skimpy, I think. But, it certainly does prove the point I made earlier; you are most definitely a sexy young lady."

"Well, thank you for that. I am also an adult, and I don't intend to change my clothes. You'll just have to deal with it. I want to feel sexy." Amy always had been a bit stubborn. During our very brief chat at the kitchen counter, she had downed her first glass of wine. I had made my attempt at being a dad, so I dropped it. I was still a male, and if she was going to dress like that, I would do my best to enjoy her display without being too obvious about it. I poured her another glass of wine, and we headed into my living room to watch a movie. We plopped down on my primary TV watching sofa, which was about the size of a love seat, and had separate reclining cushions, so only a few inches separated us as we relaxed. Amy immediately put her seat in the reclining position, causing her breasts to be quite prominent under her tee. I avoided looking at her as she grabbed the remote and started paging through the premium channels to see what was playing. She asked what I wanted to watch, and I made the mistake of not giving her any guidance, telling her to pick whatever she wanted.

And, boy, that was a mistake. After paging through several movies, she focused in on Lingerie, which was playing in back to back shows on one of the channels. "Oh, boy," she said. "One of my girl friends said this was really hot. I haven't seen it, and I want to." She selected it on the remote as she finished her sentence." I noted a light slur in her voice, and realized that she was already feeling the effects of the alcohol.

"Oh, shit," I thought to myself, knowing what was coming, having watched many of the episodes already. How was I going to handle this? I didn't have a clue, but I was thankful that I was wearing my loose lounging pants, so that when my erection happened, as it likely would, it wouldn't be blatantly obvious. But, I had no clue how to cool this situation down. Amy seemed hell bent on watching soft porn with me, and she was going to do it while wearing next to nothing. Her being slightly drunk, on top of her stubbornness meant I had little hope of redirecting the evening, short of begging off and going to bed. I'm a normal male, and would usually jump at such a chance to enter into an evening like this. My resistance had nothing to do with her being married; it was just that she was my step-daughter, and I was supposed to behave like a Dad, not a lecherous old man. On top of that, she was dealing with marital issues, and her sexual self-esteem. I'm not a psychiatrist, but I've learned a few things over the years, and I knew that Amy was definitely a very conflicted young lady. The last thing she needed was me taking advantage of the situation.

My timing was lucky, since she had selected the channel at just the time between episodes, so only commercials were on. They were bad enough, showing a significant amount of female flesh and clearly advertising some of the sexually charged series on that particular network. She finished her second glass of wine while the commercials were still on, and helped herself to another, announcing to me, "I'm going to get sloshed tonight. I deserve it, and I hope you'll forgive me. Have some more."

She refilled my glass without giving me the opportunity to decline, telling me that she knew I had at least another bottle of wine, so we needn't worry about running out. As if that was my concern. As soon as she had refilled my glass, she bopped off the couch and walked across the room to the light switch. I couldn't help but watch her as she did so, enjoying the delightful view of her gorgeous round ass under the shorts. The crease between her ass cheeks and her thighs was visible under the shorts, and my lower brain forced me to watch her with covetous eyes. She dimmed the lights and turned around to return to the sofa. Fortunately, with the lights dimmed, I could openly leer at her breasts barely hidden by her tee. The nipples were prominent, and I wondered if she was already aroused, or how much larger they might get as she watched the upcoming show she had selected. But I was thankful that she dimmed the lights, as it would make my eventual bulge less obvious. And, I knew that I would be masturbating to thoughts of Amy when I finally did climb in bed later. It wouldn't be the first time for that, but before I had only been able to imagine her body. I didn't need any imagination tonight; I saw everything I needed to see.

She settled back into the sofa and sipped some more of her wine. After the trailers for the show played displaying considerable flesh, and making it very apparent that sex would be obvious, Amy paused the show and turned to me. I was already struggling with the situation, but it only got worse after her next comments. I wasn't sure whether Amy was talking or the wine, but it didn't really matter.

"Dad, I hope you don't mind, but I'm going to relax and enjoy the rest of the evening. I'm already horny as hell, and I'm looking forward to watching this. David won't watch stuff like this with me, and according to my girl friend, this show drives her crazy. Sexy, crazy. I'm horny, a bit drunk, and watching TV with someone I trust completely. So, please let me relax, and enjoy an escape this evening."

"Ummmmm," was about all I could muster.

That didn't stop her. "Oh, and," she continued. "I know you've been ogling my body. Don't stop. I want you to. I want to know that a man finds me sexy. Even more, finds me hot. So, for the rest of the night, you are not my dad; you're just a man. Can you do that?"

"Hmmm. I'm not sure."

"Do it for me. Please!"

"Hmmm. Okay. I'll try." My cock was already reacting, so I knew that my lower brain would win on this, and she would get her wish. I just hoped that there would be no recriminations later when she sobered up. By that time the show had started, and we settled back to watch. The show started out normal enough, but about seven minutes in the first sex scene started between a man and a well endowed blonde. It wasn't long before her clothes were off, and he was actively playing and sucking on her breasts. My cock hardened fast, probably more from the sexual tension associated with having Amy sitting next to me than from the actual activity on the screen. When the man lowered his face to the woman's pussy, I stole a glance at Amy. From the glow of the TV, I could see that her nipples had hardened, and she seemed to be clenching her thighs together. It was pretty obvious that she was quite turned on, and my mind wondered how this would proceed.

Within a minute or two, the man had turned the woman around and appeared to be fucking her from behind. If you're familiar with the series, you know that while most of the woman's anatomy is bared, the man's hard cock remains unseen. I could hear Amy's breathing get shallower, and her eyes were glued to my 55" screen. Her hands were on her thighs, and as best I could tell, she was firmly squeezing her thighs with her hands. As for me, my cock wanted attention, but over the years I had learned to enjoy the buildup of watching porn, so I felt little urgency to touch or stroke my cock. I've been known to watch an entire porno without touching my cock, just to make the ultimate release so incredible.

The couple finished copulating in the missionary position, and the plot continued. "That was it?" Amy asked.

"What do you mean?" I asked, knowing full well she was wondering why she didn't get to see his dick.

"Well, it doesn't seem fair; you men get to see all of her, and we don't get to see his hard cock. What's with that?"

"It's soft porn," I explained. "It's all you get on cable TV, unless you order the porn channels."

"Oh," was all she said, as she returned to watching the show.

We continued to watch, and several minutes later, two of the women got into a lesbian scene. We watched as they undressed each other, and eventually moved into a 69 position. As with most men, I love watching female-female scenes, and my cock hardened to its full length, as I watched them play with each other's pussy. Both were completely shaved, which I find totally sexy, and I found myself enjoying the scene. While I hadn't forgotten about Amy's presence, I had stopped observing her while I enjoyed the scene, but she was watching me it turned out.

After the two girls brought each other to orgasm, and the show returned to the plot, she commented, "I see that you enjoy watching two women make love."

Once again, caught short for words, I stammered, "Well, yes, it's pretty hot."

"Oh, then did it turn you on when you found out I was fooling around with another girl in high school? Did it make you hard?"

"Mmmm, well yeah it did, actually."

When she heard my answer, she paused the TV again, and turned a bit to look at me, and asked, "Did mom know that it turned you on?"

"Mmm, well, yes she did." Now, where was Amy going with this?

"Was she mad at you for it?"

"No, I'd say she was definitely not mad at me." My oblique answer only increased her curiosity.

"How did she react? Did she say anything after I left that evening, when I told you guys?"

The situation was going from bad to worse. I could still remember the wild hot sex her mom and I had had that night after Amy had told us of her lesbian lover. I try to avoid lying about my sexuality as it only gets me into trouble, but I knew we were in dangerous territory, and I didn't feel like revealing her mom's intimate thoughts and desires. I tried to deflect the conversation, but Amy was adamant.

"Come on. Tell me. I really have no knowledge of Mom's attitude towards sex and towards me and my sexuality. We never got to talk about it. Please."

'What the fuck,' I thought. "Well, if you must know, we were both quite turned on after you told us, and that night we fucked like crazy."

"Were you thinking about me when you fucked?"

"Occasionally, I guess. Your mom was one hot sexy woman, and she could drive me crazy in such a way that I didn't need much in the way of fantasy. But, yeah, I thought about you making love with another woman."

"Gawd, that is so hot. Did mom know?"

"Well, yeah, she did actually. She even egged me on a bit, telling me how hard my cock was because of you. Since you're going to demand to know, she rode my cock to several orgasms by telling me to think about your pussy being licked by another girl."

Amy, who had been looking into my eyes, lowered her gaze to my crotch, where there was no way I could hide my bulge. But, moments later, her eyes returned to mine.

"Well, to be honest, your imagination was probably hotter than the reality. We only fingered each other's pussy while we French kissed. But, I can tell you this, Becky did get my pussy sopping wet, and her fingers were better than mine at delivering an orgasm. At least then they were."

Now, it was my turn to press for details, since she had opened the door. "Why was that all? Why didn't the two of you explore further?"