Comforting My Step-Daughter

{Author's note: It is highly advised that the reader would have already enjoyed the pleasure of reading the first two chapters before diving in for full background. No matter, though. Dive in and enjoy. Oh, and don't forget to vote.} I was not surprised when I received an email from Cindy the next morning, inviting me to lunch. I knew that, like me, her mind had been working on our oncoming potential train wreck with Amy. Our extensive collections of amateur porn, photographed in her loft and my house were very likely to disturb Amy, no matter what we had done over the weekend. And I wasn't sure that Amy was ready to learn the whole truth about her mom. Through exchanging emails, Cindy and I agreed to meet for lunch and discuss how to protect and eventually reveal to Amy our extensive collection of amateur porn.

We met at one of our favorite restaurants where we could have a conversation with minimal likelihood of being overheard. After ordering our sandwiches and beers, our conversation turned to the matter at hand. It didn't take us long to reach agreement on the fact that we both wanted to continue our sexual interaction with Amy. Cindy made it very clear to me that she was really looking forward to more play time with my step-daughter, and she knew me well enough to know that I would take advantage of the availability of another sexy woman in my life. Further, we quickly agreed that we would eventually reveal all to her, as neither of us wanted to engage in any form of deceit. But, we decided that we needed to manage the way in which Amy discovered just how wild we really were.

We then chatted a bit about some of the naughty things we intended to do with Amy when she was being our slut toy. Compared to Cindy, me fantasies were relatively benign, as I imagined Amy dressed in a sexy maid uniform, and submitting to my sexual demands as she went about doing assigned chores around the house. Cindy shared with me that she was looking forward to tying Amy to the bed, and then ravishing her completely, both as a lesbian lover, and as a dyke with one of her large strap-ons. Cindy even mused about having one or more of her other girl friends over to share in the playtime with Amy. I allowed as how I would love to be in her closet watching her play out the fantasies. Cindy smiled at me and promised she would try to make that happen at some point, taking the opportunity to describe to me in great detail the things she intended to do to Amy. Needless to say, by the time we had finished lunch I was aroused. We got up from the table and hugged and kissed.

Breaking the kiss, Cindy asked if she was the cause of my obvious erection, the smile on her face clearly indicating that she already knew the answer. Later that night, I enjoyed some solo masturbation with vivid memories of Amy and Cindy playing in my head. I have always enjoyed the mental reruns of great sex, and this was one of the better nights.

I didn't hear from Amy for several days, and had pretty much figured that her offer was given in the heat of the moment, and after some contemplation, she would want to back down. It would be okay with me either way; as her step-dad, I wanted her to be in control of her own life and happiness, and would not hold her to her promise. On the other hand, I was certainly excitedly anticipating some more wild sex with her in some form or another.

On Thursday of that first week, I received an email, in which she told me that she was moving out of the apartment with her husband, and sharing an apartment with a girl friend. The last couple of lines really got to me, "I want to fully explore my sexuality, and I want you as my mentor and wiki, and to help me stay safe. David is a wet blanket, and I can't do it with him around. Will you be my sex wiki?"

I replied immediately with a simple answer, "I'd love to be your sex wiki!" I closed it with a bunch of smiley faces. I forwarded the exchange to Cindy, and she was equally effusive with the idea. Within minutes, I received an answer from Amy, thanking me for agreeing, and inviting me to dinner for the following night at her new apartment. I accepted, of course, expecting a quiet dinner with my step-daughter.

I showed up at her apartment fashionably late at several minutes past 6PM. She opened the door and, while mostly hiding behind the door, welcomed me in. As soon as I was in, I saw her completely. She was HOT! She was wearing a simple black and white tight fitting mini-dress that ended less than inch below her crotch. It had an extreme v-neck line that plunged to well below her breasts, and barely covered her nipples, exposing a considerable expanse of her inner breasts. She was wearing stockings and a garter belt, which was fully exposed, and accented by 5 inch stiletto "fuck-me" pumps with straps that wrapped around her ankles. My eyes took their time to explore the delightful vision in front of me, which she noticed. She then very slowly did a pirouette, and I got to enjoy the rear view. The dress was virtually backless with just a strap around her neck, and enough material to barely cover her ass.

"Do you like?" she asked, when she finished her pirouette and once again faced me.

"Oh, yes." I answered. "What's not to like? You are absolutely HOT! And sexy!"

"Mmmm. Good!" she said as she stretched up to give me kiss that was inappropriate for father and step-daughter.

I followed her into their living room, where I met her new roommate Julie. Julie had been one of her high school friends, but I hadn't seen her in years. Julie was stretched out on their couch, casually dressed. Well, sort of. She had on a tee-shirt that said very boldly across her boobs, "Enjoy the view". She was clearly not wearing a bra, and her nipples were visibly protruding against the fabric. She also had on a dark pair of panty hose, over which she was wearing a skimpy pair of lime green shorts that barely covered her pussy. Her body was near perfect. She appeared to be about 5'9" with a gorgeous figure that I estimated at 36-24-34, with long muscular legs. Her smile was contagious, and when my eyes finally met hers, I could tell that she knew I had given her the once over, visually. And her first words to me indicated that this was likely to be an interesting evening.

"Hey there, Mr. P. Good to see you again. Am I as hot and sexy as Amy?"

"Mmmmm. That would be a Yes! Most definitely," I responded, wondering where this evening might be headed.

"Mmmm. Good," she said. She then informed me that her boyfriend would be joining us a bit later.

And then Amy added with a big grin on her face, "And we have some special plans for after dinner."

"Sounds like fun," I answered.

I followed Amy into the kitchen and we chitchatted while she finished a simple meal of basted chicken, asparagus, and a green salad. As we chatted, Julie brought us a joint to share, along with the wine that Amy had poured. We smoked the joint and Amy shared with me her current feelings about moving out of the apartment from her husband. Although I was concerned about her emotional state, I was pleasantly surprised as we chatted to realize that she had given it great thought, considered all the possible choices, and possible outcomes. Most importantly, I understood that this decision was a really important step in her maturing as a sexual woman. Overall, she seemed quite comfortable with the current state of her life. I was hoping I was seeing her real feelings, as I didn't want to see her emotionally bruised over some sexual issues with her husband.

Every once in awhile, I would pester her with a question about the plans after dinner, but I couldn't get a hint out of her. Just before dinner was ready, I heard the doorbell. A moment later, Julie came into the kitchen with her boyfriend. Julie introduced him as Sam, and I shook his hand. He didn't say much more than hello though. He stood about 6'3", and was most definitely one hot piece of male eye candy. His t-shirt accented his tight abs, and there was no doubt that he had a nice piece of meat in his very tight jeans.

As Amy served up the dinner, we shared another joint. Conversation was minimal as we each held our tokes as long as possible. We sat down to dinner, and Amy and Julie led the conversation, and I quickly noted that generally it was a three way conversation between the two of them and me. I'm sure that Sam said no more than five words through the entire meal including the ice cream dessert. I wondered quietly to myself what kind of relationship Julie and Sam had, as he came across as purely a boy toy. After dinner, I helped Amy with loading the dishes into the dishwasher before we joined the others in the living room.

There, we found Julie and Sam relaxing on the couch, smoking yet another joint. Julie had opened another bottle of wine, so we availed ourselves of another glass, and pulled a couple of tokes off the joint. As we were finishing our tokes, Sam and Julie got off the couch, suggesting that we sit there. We did, and Amy sat next to me, much closer than necessary given the size of the couch. As we made ourselves comfortable, Julie dimmed the lights and turned on the TV, then sat down on the large stuffed chair next to the couch. Sam joined her, sitting on the armrest of the chair. I was still wondering what was next.

Julie fiddled with the remote control, and moments later a DVD started playing. It only took me a few seconds to realize that it was a XXX porn flick, as the advertisements for phone sex popped up instantaneously. As the phone sex ads played, Amy whispered in my ear, "Do you enjoy phone sex?"

"Ummm, yes. As a matter of fact, I do. But, that is assuming that the girl on the other end of the phone gets into the conversation, and can carry the fantasy along with me."

She responded, "Hmmm. I think I'd like to try it some time."

When the movie title finally came up, Julie paused the DVD, and then shared, "Ok, Mr. P., we've kept you in the dark on the evening plans long enough. It's not a big deal, but Sam here isn't really my boyfriend. In fact, we have only met once, and that was to coordinate for this evening. The truth is that I hired him to be my boy toy for the evening." Wow, I pegged that one, I thought to myself. "You see, when Amy told me about her hot weekend with you and Cindy, and about how she had decided to pursue her fantasies, it gave me the guts to pursue some of my own fantasies. And that is what I'm doing tonight. I have always wanted to be in total control, sexually that is, of several people at one time. And, when I confessed that to Amy, she begged to be part of it, and wanted to invite you. Sorry to surprise you, but I hope you're cool with this. I'm hoping that you're willing to let me direct the events for the rest of the evening. For a long time, I've fantasized about directing my own porno movie. That's what I want to do tonight, only we won't be filming anything. If you don't want to participate, just say so, but I hope you'll play along."

The pleading look on her face was compelling, but I really didn't need any coaxing; after all, is there any red-blooded heterosexual male that wouldn't jump at such an opportunity? Or at least, want to? I was already smiling in anticipation before she finished and I willingly agreed to participate in her fantasy. As Julie restarted the DVD, I whispered in Amy's ear, "Do you know what she has planned?"

She whispered back, "I haven't got a clue, but I know two things. She hasn't had a man in weeks, and she is very loud when she masturbates. Oh, and I committed to do whatever she told me to do. She actually made me promise that twice, telling me that she wanted it to be really wild and kinky. And, she wanted to make sure that I was willing to be the center of attention."

"Well, that should make it interesting," I remarked to Amy. "And very erotic!"

"I'm pretty sure it will be. My pussy has been wet all day, thinking about it. I am so fuckin' horny. Earlier when I went in to take my shower, I was masturbating in the shower. Then Julie came in and ordered me to stop. Right now, my pussy is absolutely begging for attention. If it hadn't been for my promise to Julie, I would have already had you naked and fucking me."

"Hmmmm! That sounds nice. Somehow, though, I'm sure that she'll give us plenty of opportunity to play."

As soon as the movie title came up, we had a hint as to how it would start at least. It was a parody of a "Chippendales" show. Before we knew it, the men on screen were dancing nude in front of a bunch of women. Their cocks were clearly huge, even though they weren't fully aroused. Julie told Sam to bare his cock as well, making it clear this was going to be an active session, not one of watching the video. Sam did as he was instructed. He arose from the arm of the chair, and moved over to where he was standing next to the TV, and in front of the three of us. He then crossed his arms and moved his hands to the opposite shoulders. Then, swaying to the music, he sensuously slid his hands down his arms, until they landed on his hips. Once there, he gripped the bottom of his tee shirt and slowly pulled it up and over his head, revealing an obviously well-toned chest.

Amy mewed next to me, whispering, "My god, he's a hunk."

He threw his tee shirt aside and then moved his hands to his belt buckle. But before he undid the buckle, he slid his right hand slowly across the obvious bulge in his tight jeans. I noticed his eyes making contact with Amy's and I looked at my step daughter and saw that she was staring right back at him. He then moved a little closer to Amy and slowly unbuckled his belt. His eyes never left Amy's, as he slowly unzipped his jeans. He pulled the flaps of his jeans back, revealing that he was commando. His large cock sprang free, already semi hard. By now, the men on the video had their cocks out and were stroking them up close and in front of the women's faces. Sam followed suit and started stroking his cock, only a foot or two in front of Amy. Amy's eyes were fixated on the monster cock in front of her, as it hardened in his hands. I glanced over at Julie, and saw that she too was watching the slow tease happening right in front of us. Her nipples had hardened and were poking firmly out against her own tee.

"Amy, get down on your knees in front of Sam, and stroke his cock for him. Make him real hard."

Amy slid off the couch instantly, and dropped to her knees in front of Sam, positioning herself so that Julie and I had a full view of her stroking his cock. He dropped his hand from his cock, allowing Amy full access to his man meat. She slid her right hand up and down his cock, while her left hand cupped his cleanly shaved balls. By the time his cock was fully engorged it had reached at least eleven inches in length. He was larger than several of the men on the TV. A glance at the TV let me know that scene there had quickly heated up as several of the men had their cocks in the mouths of women from the audience. My own cock was hardening quickly as the debauchery continued to heat up, both live and on video. I was about to adjust my pants to make my cock more comfortable when Julie told me to fetch the box on her bed. She pointed towards what was obviously a bedroom door.

I adjusted my own cock as I stood and then walked over to her bedroom and opened the door. It was softly lit and had several candles burning, putting out a delightful sweet scent. I entered and saw a hat box on the bed, with its lid on. On top of the box were some pictures, with a Post-it note on the first one. I quickly read the note. "I took these pictures for you, Mr. P. I hope you like them. Enjoy looking at them before returning to the living room. Take a few minutes before coming back to the living room. Julie." I lifted the note off the first picture revealing Julie lying on her bed with the skimpiest of string bikinis on. She was lying back against a pillow at the head of her bed, and her legs were spread. Given the miniscule size of her bikini bottom, I realized her pussy would be shaved. The next picture showed her without her bikini top on, revealing protruding nipples from quarter sized aureoles. In the third picture, she was pinching her nipples. The fourth picture provided me with the delightful view of a completely nude Julie, as her bikini bottoms were now removed. The next several pictures were close up of her tits and pussy. In the later pictures her fingers had her pussy lips wide spread, clearly showing her arousal level and the juices oozing from her cunt. In the final few pictures, her fingers were plunged deeply into her pussy.

It didn't take me more than a minute to look through the pictures, so, to pass the time as she had requested, I went ahead and opened the box. As I expected, it was her toy box. It was a fairly typical toy box. She had a small collection of vibrators and dildos, a vibrating egg, a couple of boxes of condoms, some lubes, and one small butt plug. A couple of items piqued my interest even more. The box contained a pair of nipple clamps, and a collar. I wondered to myself whether Julie had actually used them, and whether or not she was dom or sub. I had pegged her as being dom, but this made it interesting. I put the lid back on the box, but before returning to the living room, I snooped. Shame on me, but after opening her toy box, I couldn't resist. I was blown away, when I opened her closet, finding two things that were real surprises. The first was a Sybian, that very expensive fucking machine, and a restraining device for wrists, ankles, and head. It was a very nice high end piece of bondage gear, consisting of a steel tubular frame that had four restraints on extended arms on the floor, one each for each ankle and wrist, forcing the detainee to kneel on the floor with their legs spread wide, and their arms wide as well. Between the arm straps, a frame came off the floor about 2 feet, ending in a fifth restraint that clearly was to restrain the neck. My cock, which had softened a bit, re-hardened as I imagined Julie fully restrained by this device. I contemplated snooping through her drawers, but decided against; I already had considerable insight into this young lady.

I closed the closet door, and picked up the box on the way back to the living room. When I returned to the living room, Amy was no longer just stroking Sam's cock; she had her lips wrapped around it, and was clearly delivering a delightful blowjob, as I heard him moaning in happiness.

Julie egged her on. "Oh, yeah, Amy. That is hot. Suck his cock." Seeing me back in the room, she added, "And you're doing it right here in front your step-dad. My pussy is already soaking wet watching you." Julie was massaging her own breasts through the thin material of her tee shirt, and I found myself wanting to do it for her. Understanding that Julie was to be in control of the scene, I allowed myself to passively enjoy the activity taking place both on the TV and live no more than a few feet in front of me, so I returned to the couch. On the screen several male dancers were enjoying having their cocks sucked by women in their audience. My cock was hard now, as the erotica surrounding me, combined with the wine and smoke, and I what I had learned about Julie increased my arousal level.

"Mr. P., take Amy's dress off." Julie was clearly enjoying the power that we had allowed her to claim.

I arose from the couch and moved over behind Amy, who was still running her lips up and down the hard shaft in her mouth. I grasped the neck strap of her dress and easily lifted it over her bobbing head. Amy allowed Sam's cock to slip from her lips, just long enough for me to lower the top of her dress to her waist. She returned to her assigned role, as my hands slipped down the sides of her body to her waist, where they caught up with her dress, which was now hanging on her hips. I slipped my fingers into the dress and pushed it over the sexy ridge of her hips. Once, I slipped it over her hips, it fell to the floor. Amy now stood there, dressed only in her shoes, hose and garter.