Teaching the Sis-in-Law

This story is a recurring fantasy I have. Names have been changed to protect the lusted after. Hope you enjoy it.

My wife, Sandy, has 3 sisters, one older and two younger. I've lusted after all of them over the years. I've fantasized about three-ways and more somes with them more times than I can recount. They're all beautiful in their own way. There's only one problem. They won't have sex with me! Well, they didn't until Kathy needed some help.

Kathy is the third oldest in the family. She's an ultra conservative Christian and claims never to have had sex. Since she's 40, the sisters and I are quite skeptical about her claim. Still, she's always been chaste and wears turtleneck sweaters and long sleeved blouses, even in the summer. She claims she's allergic to sunlight. Yeah, right.

I came home from work one day to find Sandy, my wife, and her sister Kathy at the kitchen counter drinking wine. They quickly cut short their conversation when I walked in.

"Hi beautiful, or should I say beauties"

"Hi honey," my wife replied. "How was work?"

I leaned over the counter and kissed my wife.

"Oh, the usual. Same ol', same ol. How're you doing my beautiful sister?" I asked as I gave Kathy a kiss on the cheek.

"I'm okay, I guess," came Kathy's reply.

I sensed something was up since Kathy rarely drinks any type of alcohol. I excused myself and headed upstairs to change clothes. My wife followed me up the stairs and into the bedroom, closing and locking the door behind her.

"How's my sexy honey?" she asked as she wrapped her arms around me.

"I'm fine and what's up?" was my reply.

"What, can't a woman follow her husband to watch him change clothes?"

"Sure she can, but, when said husband finds his sister in law drinking wine when she usually doesn't, something's up."

"Okay, you got me. Kathy would like your help with something."

"And she'd like help with what? Is she moving again?"

"No, it's a bit more complicated than that. She wants to have sex with you?"

"What? That's not even funny, honey."

"I'm serious, she came over today to find out if I'd be okay with it. She knows what kind of lover you are and how much pleasure you bring me. She's not getting any younger you know. She'll be 40 in a couple of months."

I sat on the bed to think about it. This HAD to be some kind of joke. In all the years I've known my wife, she's always told me, no way Jose, on the subject of one of her sisters joining us. This had to be some kind of setup for the cruelest joke of the century.

"Yeah, right. My virgin sis-in-law has suddenly decided to lose her virginity, and she wants me to be the one to take it. Funny joke, honey, next you'll tell me that the other two want to watch. I'm not biting."

"It's not a joke, she really wants to experience what sex is all about. She feels safer with you. After all, you HAVE been faithful to me, right?"

"You know I have. This is quite shocking. Let me think about it over dinner."

We headed back downstairs to eat. Kathy avoided my gaze during dinner. We did the usual small talk and, after dinner, headed for the couch in the family room. I got us all some more wine and we sat down to talk.

"So, I've thought about your request Kathy, but, I need to know, why me and why now?"

Kathy took a sip of her wine and turned to me. "Why you? Over the past 25 years that you've known and taken care of my sister, I've come to love you. You're gentle, caring and understanding. When no one else in the family liked the decisions I made, you were there to support me. You may have not liked them either but you at least understood my need to live my own life and supported me in that endeavor. Why now? I'm gonna be 40, and I'm still a virgin. I want to know what sex is like. I want to know why people find it so necessary. I want someone to find me attractive and sexy. I want to be needed."

I looked over to my wife and she nodded her head slightly to indicate she was okay with this. I took Kathy's hands in mine, gave her a quick kiss and agreed to be her lover for a night.

"Okay, I'm willing to do this, but not tonight. You've had too much wine and I want you to be sure this is what you want."

She leaned over, gave me a kiss and thanked me. "You're so sweet. I really do love you."

The three of us then talked about nothing the rest of the night. We were all nervous and the conversations were stilted and broken up by long periods of silence. Kathy left a couple of hours later, after we had set things up for the following Saturday night. Our kids would be at their grandmother's so we'd have the house to ourselves. Sandy and I talked about it in bed that night.

"I think you've made my sister very happy"

"You think so? I guess we'll see come next Saturday night. I'm really nervous about this. I mean, she's a virgin! When you're 16-17, it's different, the expectations aren't so high."

"Don't sweat it. Hell, you've been nothing but gentle with me"

"Yeah, except for when you want your ass slapped or your hair pulled when I'm doing you from behind"

She playfully slapped me and we fell together in a naked embrace. We made energetic love and I looked forward to the challenge of taking my sis-in-law's virginity.

The week took forever to go by. Saturday came around and Kathy arrived at our house in the late evening. Sandy met her at the door and we all had a small glass of wine. After some nervous small talk, Sandy ushered her sister upstairs to the bedroom. I waited a few minutes and then headed upstairs. The ladies met me at the door.

"Okay you two, have fun," Sandy said as she headed downstairs. "Don't do anything that I wouldn't do."

Kathy and I just groaned at Sandy's poor humor.

I closed the bedroom door and walked up to Kathy. "Nervous?"

"Yeah, a lot. Please be gentle"

"Don't worry my sweet. I will be"

I lead Kathy to the foot of the bed. I gently kissed her forehead. She stiffened a bit as I moved down to her lips. "Relax, we have plenty of time." I whispered in her ear as I held her. I felt her become less stiff so I moved my hands down her back to the top of her butt. Once again, she stiffened. I moved my hands back up her back and slowly rubbed her shoulders.

"I'm so nervous, I'm sorry."

I kissed her lips gently and told her not to worry. I again kissed her lips and moved down to her neck. She moaned very quietly as I nibbled on her neck. I slowly turned her so her back was to me. I reached around and began to unbutton her shirt. As I unbuttoned her shirt, I gently stroked the skin that was revealed. It was very pale and soft. I continued to nibble and kiss her neck as I slowly unbuttoned another button. Her cleavage came into view.

I slid one of my fingers down her cleavage. She tensed up again and apologized. "Shh, please, don't worry," I consoled her. "If you want me to stop, I will"

"Please, I need some time."

I closed her blouse a little and just held her. I stroked her hair and massaged her arms and shoulders. Soon, she was pressing back into me and gently took my hands and placed them on her breasts. I felt her chest rise and fall with her breath. I slowly massaged her breasts through her blouse and bra. I felt her nipples stiffen. I gently pinched one and heard her sigh quietly. I resumed unbuttoning her blouse.

I removed her blouse and watched her reaction in the mirrors above the headboard. Her eyes slowly opened and she smiled. I ran my fingers over her bra cups, teasing the flesh beneath. Her hands covered mine and she stopped me for a minute.

"Can you turn the lights off?"

"No, I can dim them, but I want you to see how beautiful you are."

She asked me to dim them and I did. I still had plenty of light to see her body. I kissed her shoulders where the bra straps were and gently, slowly removed one strap and then the other. Her hands immediately went up to her bra cups and held them firmly against her breasts. I covered her hands with mine and slowly pulled them away. She closed her eyes again as I unhooked her bra.

I slowly removed her bra. Her breasts were lovely. Probably a large C-cup with a beautiful, slight sag to them. She immediately covered her breasts again.

"Don't," I whispered in her ear. She slowly lowered her hands and her breasts came into view. I reached around and started to gently trace the outline of her breasts. She leaned back into me and tilted her head back. I kissed her on the lips. She returned the kiss a little more forcefully this time and I could feel her breath becoming quickly. I guided her hands backwards toward my cock. She jumped a little when she felt it and withdrew her hands. I continued to massage and caress her breasts.

"You have beautiful breasts," I whispered in her ear. She giggled nervously but continued to watch me in the mirrors. I took her hands and once again guided them to my cock. This time she didn't jerk her hands away and proceeded to rub me through my pants. I moved my hands down her sides to her skirt. I ran my thumbs along the waistline to the back. I unsnapped her skirt and slowly lowered the zipper. It was a long skirt that fell close to her ankles. Kathy sighed and allowed me to remove her skirt. How quaint. She was wearing "Granny" panties. Pretty much what I had expected.

I turned her towards me and she stepped out of her skirt. Again, a little nervous laugh escaped her lips. I tilted my head down to hers and kissed her again, a bit more forcefully this time. She returned the kiss and ran her hands over my cock. I whispered in her ear that it felt good and she looked up at me and smiled.

"You're just saying that because you want to get into my panties."

I laughed a little and said, "You're right!"

I allowed her to undress me, first the shirt, then my slacks. Her hands were busy exploring my body. I leaned down and took a nipple into my mouth. She sucked in her breath sharply, as I nibbled gently on her nipple. I ran my hands over her panties and grabbed her ass. She arched her back a bit and I felt her jerk slightly. I moved over to her other breast and suckled on it for a while.

She lowered her arms and let me have my way with her body. I kissed up and down her body from head to toe. I traced her panty line with my tongue. I could smell her arousal. I purposely avoided her pussy, not wanted to scare her more than she already was. I made my way back up to her face and kissed her gently while turning her around. I then moved my hands down to her panties and began to remove them.

"Wait!" she cried. I stopped. Her breathing was ragged. "I'm, I'm not ready yet." She whispered softly.

"Okay, there's no rush. Did you want to explore my body some more, or, would you rather I continue to caress you?"

She smiled at me and I began to stroke her body again. I massaged her shoulder and breasts and kneaded her ass cheeks. Her breathing, once again, became ragged. I kissed her shoulders and neck and moved her hands to my cock. She stroked it more fervently this time; she even pulled it out of my boxers. I groaned into her hair as her hands moved up and down my shaft.

"Does that feel good?"

"Hell yes!" I replied. "Very good"

She continued to explore my cock with her hands. I continued to rub her body and stroke her hair. "Maybe we should move this to the bed." I said.

"Yes, I think we should."

We moved to the bed and I laid her down. I moved over her and I saw panic in her eyes. "Don't worry, I know you're not ready yet. Just let me explore your body some more." She nodded in agreement and I began to kiss and stroke her body. I kissed and suckled her breasts and made my way down her stomach. I, once again, kissed around her panty line and then proceeded to massage her legs. Kathy began to relax once again and I continued to stroke and caress her body.

I then made my move for her panties. I hooked my thumbs in them and slowly began to remove them. Kathy lifted her hips and bit and let me take her panties off. I looked at her pussy. It was quite hairy. My wife keeps hers' shaved so it was quite a different look.

"Something wrong?" She asked.

"No, everything looks fine to me." I replied.

I bent down to kiss her pussy and she quickly closed her legs. "What are you doing?"

"I want to get a better look at you." I smiled. I blew some air on her triangle and she raised her hips a bit.

"Oh, that felt nice." She whispered.

"Just wait, it's about to feel much nicer." I leered back.

I bent forward and ran my tongue over her pussy hair. She squealed that it tickled. I gently parted her legs and ran my tongue over the inside of her thighs. She moaned a bit and opened her legs a bit more. I positioned myself across her legs and let my cock rest on her feet. She began to massage my cock with her feet.

I kissed my way back up to her pussy and gently kissed it. Her hips rose off the bed and she moaned again. "See, I told you it would feel much nicer!" She just smiled at me and put her head back down. I again gently blew air on her outer lips. I felt her legs jerk in response. At this point, I figured it was now or never. I moved my face forward and licked her pussy lips.

A soft moan escaped her mouth. "What are you doing? That feels so good."

"Do you want me to stop?" I asked her.

"No, just be gentle, I've never done this before." Well, duh, I though to myself.

I moved forward and began to lick at her pussy. I ran my hands up over her legs, across her stomach and latched onto each nipple. They were hard. Her breasts were a delight to fondle, nice and firm. My wife, because she breastfed our kids has lost some of the firmness. Not that I'm complaining though, I love breasts however they hang!

Her hips arched up to meet my face. I felt her hands cover mine on her breasts and then she moved them down to my head. She pulled my face closer into her pussy. I ran my tongue up and down her outer lips and then plunged it into her pussy. She came. Hard. Her legs wrapped around my head and her hands crushed me to her pussy.

I love when a woman comes on my face. I love the taste of her juices and the feeling of her pleasure. Kathy was no exception. She began to wail, tears flowed from her eyes. I stopped licking but she just grabbed my head and forced me back onto her pussy. I drove my tongue into her again. She wailed again. Her legs shook wildly; her feet felt so good on my cock that I came, showering her feet and ankles with my cum. As my cum hit her skin, she came again, even more violently this time. Her eyes rolled back into her head and she stopped moving. I moved off of her and lay next to her. I got up and got a washcloth and towel and cleaned her feet and ankles of my cum. She lay there, breathing gently. I began to stroke her body again.

My wife opened the bedroom door. "Everything okay in here? I heard someone wailing."

I turned to her, "I think your sister came for the first time."

Sandy just smiled, thanked me and closed the door. "Have fun"

I looked over at Kathy and smiled. Her body was beautiful stretched out like she was. A little extra padding here and there but nothing that would cause her to cover up like she does. I gently began to caress her back to reality. She opened her eyes and looked at me.

"You okay?" I asked.

"What was that?"

"I think that was your first orgasm." I replied.

"How come my feet got so wet?"

"Oh, that, well, I was so excited I came on your feet."

"Really? You're kidding me, right?"

"Nope, your feet felt so good rubbing my cock that when you came, I came."

"Wow, that's cool."

"Very." I said. "Ready to try some more?"

"Sure, I guess. Maybe."

"I don't want to push you if you're not ready"

"No, it's okay. Just let me catch my breath here."

I continued to gently run my fingertips over her body; face, neck, shoulders, breasts, stomach, pussy and legs. She closed her eyes again and just sighed. I leaned over and took her nipple in my mouth. Her eyes shot open again.

"Are you ready to try penetration?"

"I think so. Maybe, I don't know. Yeah, I think I am. If it's anything like when you put your face down there, I may pass out again!"

"Well, I'm ready to try." I moved her hand over to my cock. "See?"

"Why, yes, yes I do." She smiled. "Just please be gentle."

"I will Sweetie, I will."

I moved over her. I kissed her and ran my fingers over her body again. I spread her legs a little and positioned my cock at the entrance of her pussy.

"Is it gonna hurt?" she asked with concern.

"It might, just please let me know if it becomes too painful" Now, I'm not overly well endowed. In fact, I'm just a bit above average in length, 6.5" to be exact. However, we were talking about a 40-year-old virgin, so I wanted to make sure she understood she could stop me whenever she wanted.

I pulled out a condom and put it on. I have kids already. I don't need another one. I rubbed the tip of my cock against her pussy lips. Every time I came near her clit, she jumped a bit. I reached down and felt her. She was very wet. I rubbed my cock against her again to get some lubrication.

"Are you ready Kath?"

"Uh huh." She said as she gritted her teeth.

"Okay, here we go." I pushed gently against her outer lips. Nothing. I tried again and made little headway. Damn, she's gonna be very tight, I thought to myself. I pushed again and just the very tip of my cock entered her pussy. She clenched up.

"You okay?" I asked her.

"Yes, I'm okay. I guess its like being at the dentist, even though he numbs you, you still react to his motions."

I smiled at her and continued to try to get into her tight cunt. After about 10 minutes of trying, I had only gotten the head in.

"I'm too tight, aren't I?"

"Well, you're definitely tight Kathy. Are you okay? I'm not hurting you am I?"

"No, you're not hurting me. I probably wouldn't be so tight if I'd tried this earlier now would I? I mean, I could have least touched myself or something."

"Don't worry about it. We have nothing but time."

"At this rate, your kids will be back home before you get in me."

I laughed a little. "Okay, let's try something different. You ride me."

"What? What do you mean?"

I got off of her and explained that I wanted her to mount me. That way, she could control how deep I got when I finally loosened her up enough. I also wanted to play with those gorgeous titties of hers.

I lay on my back and she moved over me. I lined myself up again and she proceeded to push down on my cock. Once again, it was very slow going, but soon, I felt some more of my shaft go in. I looked up and Kathy had this far away look in her eyes.

"You alright?" I asked.

"Oh yes," she hissed, as she drove down on my cock. "Very alright"

Suddenly I felt pressure on the tip of my cock. I heard Kathy mumble something about now or never and then she pushed down hard. I felt the pressure release and also felt a teardrop on my face.

"Kath, are you okay?"

She looked down at me with tears in her eyes. "Yes, I think so. The pain is going away. Your penis feels so good in my vagina. I feel so full."

"Okay, just take it slowly, okay?"

She murmured her approval and began to slowly ride my cock. I reached up and began to knead her breasts. She arched her back and drove herself down on my cock a little harder. I smiled. This is gonna be one hell of a ride.

I massaged Kathy's tits as she slowly rode my cock. As her pussy began to lubricate better, her downward strokes became deeper. Once again, her eyes rolled into her head and she came. I felt her pussy contract on my cock and I squeezed her nipples. She let out a very low groan and ground her clit against my pubic bone. She was mumbling incoherently and then screamed. Her pussy was contracting rhythmically around my cock. Damn! She felt so tight, almost like she was sucking me!