Teaching Step Daughter About Sex

This story is partly true and partly fiction. It contains a graphic description of at least one sexual act and includes voyeurism, mild BDSM, cross-dressing and family members. If this type of thing is not to your taste, you probably don't want to read it.

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I got home about 6:30 on a Thursday night after work, and, as was my habit, I went over to the bar in our entertainment room and made myself a gin and tonic to drink while I went through the mail. In a few minutes, Ginny, my wife of about ten years, joined me from the kitchen. I made her a drink and she sat down with me at the bar. She and I would often have a drink at the end of the day and catch up.

Tonight she seemed a little worried. "Bob," she said, "we have a problem."

"We do?" I asked. I admit I wasn't paying a lot of attention. Usually our problem was that the dog needed to go to the vet or the plumber needed to check a leak in one of the bathrooms.

"Yes, and it's a serious one," she replied.

"OK, I'm all ears. Tell me about it," I said.

"Well, you know Katie is a virgin," she began. Katie was her 21-year-old daughter by a previous marriage. She was a senior in college and was planning on attending law school next fall. Her sex life was not something I considered by business.

"No, I didn't know that," I answered, "but that seems to be Katie's problem, not ours and it's none of our business."

"It is our business in a way. She has been talking to me about it. She knows she's smart, attractive, and has a great personality, and she has plenty of young men interested. It's just that when the time comes to actually 'do it' she chickens out. The biggest part of the problem is that now she's dating a guy she really cares about and she wants to have sex with him."

"This sounds like a mother-daughter thing to me," I said. "Maybe she needs to see a counselor."

"I have another solution," Ginny said. "I thought that if she could see how much fun it is for two people who really love each other to have a great fuck session she would be less afraid."

"What do you mean?" I asked.

"Why don't we let her watch us fuck?"

"You're not serious," I replied. "I'm not sure that's a good idea at all."

"I think it's a great idea. Think about it and we'll talk later."

I did think about it. It was arousing in a way but also a little creepy. Katie and I had a good relationship, but I was not her father. Since she had her own place near the campus, I walked around naked a lot at home, but never when she was there. I'm not sure she had ever seen me in my underwear. We were friendly, she respected the fact that I was married to her mother and I think she liked me, but that was the extent of it. Still, there was an element of excitement about being watched.

The next week I cam home Friday and Ginny joined me for our late afternoon libation.

"Have you thought about what we talked about last week?" she asked.

"Yes," I answered, "but I'm still not sure. It is exciting and if it will help Katie..."

"I thought you might find it arousing." Ginny said. "I've discussed it with Katie and she's up for it."

"There are some practical considerations," I said. "For example, are just going to fuck or are we going to reveal the whole thing?"

"All of it," Ginny said. "There's nothing wrong with a little kinky sex."

Ginny was referring to the fact that I liked to wear women's underwear. I had quite a collection of lacy thongs, boy pants, and bikinis with little bows. Sometimes I also wore garter belts with thigh high stockings. I also liked to put on a little makeup with mascara, lipstick and rouge. Ginny thought all of this was cute and it added to our lovemaking.

For her part, Ginny loved to be spanked. I used my hand, a ping pong paddle, and a whip we bought from a sex shop. It was very mild BDSM stuff, but she liked her ass to be a little red in the morning. Ginny also liked to scream when she came. Of course, she held it down when Katie was home or we were in a hotel, but she really liked to scream and to talk dirty. It was great for us, but not necessarily for public consumption.

I was still not totally convinced, but the hard on pushing against the nylon panties under my pants apparently was convinced. We agreed to put on the show for Katie one week from this Friday.

When the big night arrived, we all went to dinner at a local hang out. Ginny and Katie had a little more wine than normal to loosen their inhibitions. When we got home, they broke out another bottle of wine and were a little tipsy by about ten o'clock.

Finally, Katie said she needed to go to the bathroom so Ginny and I said we would meet her in the bedroom. When Katie returned, she was wearing a short see-through negligee and thong panties. I was a little shocked.

Noticing my reaction, she said, "I'm going to see you naked. I didn't think I had to get dressed up for that." Then she sat in an easy chair not far from the bed and waited.

Ginny had on a see through nightgown and nothing else. She moved me to the side of the bed and began to kiss me, her tongue deep in my mouth. I unbuttoned my shirt and let it fall off as Ginny worked on my pants. As they fell to the floor, I was standing there in a lacy women's thong and thigh high white stockings. Ginny stood back and smiled.

Turning to Katie, Ginny said, "Bob likes to wear women's underwear. He also likes makeup. It's a little kinky, but he's not gay. I like it and it adds to our sex life."

Katie smiled and nodded her approval.

Next, Ginny and I hit the bed and began a really hot fuck session. She took my thong-covered cock out and began to give me a blowjob while I discarded her nigh gown and watched her work on me. In a few minutes, we traded places and I was licking her clit while she squeezed her nipples. The heat was turning up and I all but forgot we had an audience. I flipped Ginny over so that she was face down on the bed. "You want to show it all?" I asked.

"Yes," she answered. Spank me. I'm a dirty slut bitch who loves cock too much and I need to be spanked."

I reached under the bed and brought out a ping pong paddle. With each stroke on her ass cheeks, Ginny would howl. "That's it. Turn my ass red. God, I'm such a whore. Spank me and then fuck me."

When we both couldn't stand it anymore, I rolled her over and jammed my rock hard cock in her pussy. 'That's it, you panty-loving sissy -- fuck me!" In a few minutes she had an orgasm and screamed at the top of her lungs, "Fuck, I'm coming. Fuck, fuck, fuck!"

After she calmed down just a little, I began to work on my own orgasm. "Cum in my cunt, you fucking sissy. Unload that big dick in me." And I did.

As was about to roll off Ginny I heard another moan and looked around to see Katie with her hand down the front of her panties obviously having one hell of an orgasm. When it subsided she looked at us and said, "Wow, that was awesome. I came twice and I'm going back to my room and come again. Thanks, guys. I feel a lot better about this." With that, she gave us both a kiss on the cheek and walked down the hall to her room.

After that night, I didn't worry about my state of dress or undress when Katie was home. There was nothing sexual between us, but since she had seen me naked and knew I liked women's underwear and makeup, there was no reason to be modest. At the same time, she was much less modest also. She often slept in a short t-shirt with no panties or bra and would come into the kitchen on mornings she was there with no more than that on.

One morning, I woke up after Ginny and I had spent the earlier evening having one great sex party. I was in drag with white, see-though bikini panties, a garter belt, and white stockings. I had on makeup, mascara, lipstick, and rouge. We had fucked, spanked, screamed and used every dirty word we could think of. It had been great. We didn't worry because we knew Katie would not be home.

I got out of bed, still in my underwear and stockings, with my makeup smeared and the night's growth of beard poking through the rouge. I'm sure I was quite a sight as I went into the kitchen to make a pot of coffee. Just as it was almost done, I heard someone say "Hi" to turn around and see Katie walk in the kitchen in a pair of black bikini panties and nothing else. I was surprised because I thought she was at her apartment, but she had seen me like this before.

The real shock was that behind her was a man about 25. He was wearing a pair of boxer briefs. I assumed, from the situation, that Katie was not longer a virgin. I however, was not used to standing around in women's underwear and makeup in front of strangers.

"This is Brad," Katie said. Brad, this is my step-father, Bob." Brad stuck out his hand and I shook it. It was a little awkward.

About that time, Ginny walked in the kitchen naked as the day she was born, her 36 D cup tits swaying as she walked and her shaved pussy on display for all to see. She looked like she wasn't quite awake yet and went for the coffee maker when she noticed Katie. In an instant, she also noticed Brad and froze.

"Mama, this is Brad and last night he took care of my problem!" Katie exclaimed.

Ginny was still trying to process what was going on. Brad said, "It's nice to meet you Mrs. Jackson."

Eventually Ginny seemed to wake up and said, "Uh, nice to meet you." Then she turned to Katie and said, "Katie, we didn't know you were here or we wouldn't have come in naked in front of your friend. I'm a little embarrassed."

"Don't worry, Mama," Katie answered. "I told Brad all about what happened and he was impressed at how much you both cared about my happiness. And don't worry about being naked, we all are or at least almost naked."

We each took a cup of coffee and then Katie started laughing.

"What's so funny," Ginny asked.

"Look at the front of Brad's shorts," Katie said. We all looked, and Brad had one raging hard on. "Did my Mama's big tits and shaved pussy do that to you, Brad?"

Brad looked embarrassed but laughed good naturedly. "I guess we should go take care of that, Brad," Katie said and led him back to her room.

Ginny looked at me and said, "Brad is not the only big boy around here."

Sure enough, my erection was peaking out of the top of my bikini panties. "Well, let's go take care of it," I said. And we did.