Teaching Lovely Lisa

Story Info
Lisa learns about sex.
4.1k words
4.48
77.5k
10

Part 1 of the 4 part series

Updated 11/02/2022
Created 06/12/2010
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
rafters11
rafters11
109 Followers

My wife Pam died in an automobile accident right before Christmas. She was killed by a drunk driver on the way home from his company's big Christmas bash. My best friend Rob and his wife Lisa were a tremendous help in getting me through this very difficult time. My daughter Melody was a freshman in college when the accident happened. Her roommate Cheryl helped her a lot.

Let me tell you a little about myself. My name is Tom. I am 6'2" tall, weigh about 200 pounds, dark, wavy hair, bright blue eyes. I travel a lot on business and work out in the hotels I stay at so I am in pretty good shape. I own 3 weeks in a national timeshare company so I can go on vacation when I want.

Rob had been my golfing partner for more than 20 years and there were no secrets between us, or so I thought. When spring rolled around Rob and I started playing our usual Saturday golf matches. Rob suggested that it was time for me to move along with my life. Pam was gone and I couldn't do anything about it. I needed to quit mourning her and start to live again. I would have been mad if that advice came from any one other than Rob.

Rob and Lisa always had a large 4th of July party at their house with Rob's business associated and friends, as well as family, invited. As usual I was invited. Melody was going to her aunts for the long weekend and wasn't with me. There was a lot of good food, beer, mixed drinks, soda, iced tea, etc.

Lisa was looking absolutely stunning in shorts, a halter top that showed just a little cleavage, her hair pulled back in a pony tail, and, as always, a big smile. Rob had married the second most beautiful women in the world. My Pam was the most beautiful. Lisa was tall, about 5'8", long dark hair, 130 pounds of taut flesh, hazel eyes that made you melt, an absolutely gorgeous face, shapely long legs, a lovely ass, and large breasts. She looked many years younger than her actual mid 40's. She worked out regularly and it showed.

I spent the afternoon eating, chatting with people I knew, having a couple of beers, and generally chilling. There seemed to be a number of unattached females at the party and Rob introduced me to 3 of them. I made small talk with them for a couple of minutes than excused myself. I left before dark and went home.

The next Saturday, when Rob and I were golfing, Rob really let me have it.

He said, "I have 3 very hot, very fuckable, women at my picnic and you ignore them. He continued. Buddy, you need to get a life, you need to get laid, and you need to get back into the world. Pam is gone."

I replied; "no one will ever take her place. I do get horny occasionally, but I wouldn't know where to start with another women. I haven't talked to another woman since I started dating Pam in college, over 25 years ago."

He thought a minute then said, we will continue this conversation at a later time.

Rob called me Tuesday night and invited me for dinner on Wednesday. I arrived on time with a bottle of good wine that I was sure they would like. I got my usual hug from Lisa, who was looking hot as hell. After dinner we went out to their patio with drinks.

Lisa asked if I was horny. I joked, only when I am around you. Rob interrupted and asked if I would like to fuck Lisa. I was floored. I had to say, are you crazy Rob?

Rob began telling me a very sad tale. He had been in an automobile accident almost 20 years ago. I commented, I remember, I visited you in the hospital. You had lower abdominal injuries that kept you in the hospital for 10 days. Rob continued; what you don't know is that I suffered permanent damage to that part of my body, and because of them I can not get an erection. Lisa hasn't had sex since the accident and she is going crazy.

Lisa said; "Rob, book a long weekend in one of your timeshare places and take me with you. We both desperately need to fuck."

I thought my best friend and his wife had flipped out. When they saw the look on my face Rob said; "Tom please do it for me." "You need a vacation anyway and so does Lisa." After much heated discussion I agreed to think about it.

Saturday on the golf course Rob asked me if I had given the subject any thought. I replied that it was all I thought about. Rob responded, "Well?"

"Rob, you are talking about your beautiful wife Lisa, not some tramp," I countered. His reply shocked me.

"If I can't fuck her someone else should, and I think right now you would be the ideal guy." "I need you to do this for me."

How could I turn down my best friend when he asked for help?

I picked Lisa up around 7:00 A.M. in Thursday, November 1st for a long weekend in the Smokey Mountains of Tennessee. We would be returning on the following Tuesday. Lisa looked fine in designer blue jeans and a bulky knit white sweater. I loaded her suitcase in the trunk and her cooler full of food on the back seat. I shook Rob's hand and watched as her gave Lisa a long hard kiss. She climbed in the car and we left for the 8 hour drive.

Lisa was pretty quiet for the first part of the trip. She napped a little. She did ask about the resort, what we were going to do there. I answered; go up into the mountains and see the beautiful colored leaves, drive through Cades Cove, shop in Sevierville, Pigeon Forge and Gatlinburg, and the normal tourist stuff. And of course we will be having sex.

Her eyes lit up like a Christmas tree. Sex is what she really wanted to talk about. Lisa asked what we would be doing sexually. I responded with you tell me. What do you want to do sexually Lisa? This trip is for you and I both to enjoy.

Lisa's answer made my cock throb and start to harden. She said; "I want to do it all. Rob and I had only been married 3 years when he had his accident. He traveled a lot so we were still in the newlywed stage of sex. It was exciting, and hot, but vaginal sex only."

"I want to fuck you in every position imaginable, I want to suck your cock, I want you to eat my pussy, I want anal sex, I want a three some, and whatever else we can think of."

I couldn't believe my ears. This gorgeous lady wanted it all. I hoped I would live up to her expectations.

We arrived in Sevierville, checked in, unloaded our stuff and found a restaurant for dinner. When we got back to the condo I fixed us margaritas and we went out to the balcony to watch the sunset. It was nice having a female companion after all of these months. Lisa seemed to feel at ease with me as we talked about tomorrow's agenda. The weather forecast was for chilly and light rain showers so we wouldn't go to the top of the mountain. When I finished my drink I told Lisa I was tired and was taking a shower and heading to bed.

As I showered I wondered what was going to happen tonight. I decided that I would go very slowly with lovely Lisa. I didn't want to make her mad at me and mess up my friendship with Rob. I would let her take the lead tonight.

When I came out of the shower Lisa was surfing channels on the cable TV in the bedroom. She immediately headed for the shower. I walked around the condo aimlessly while she showered. I was back in the bedroom watching a basketball game on TV when the bathroom door opened.

There stood Lisa in the sexiest teddy I have ever seen. My mouth dropped open and my cock started to grow just looking at her. Her outfit was red with spaghetti straps holding the top up, sleeveless, bare shoulders, and it was made of a see through material. The top ended at the top of her thighs and it was easy to see that there was no bottom to this outfit. The red color contrasted nicely with her dark hair. Her nipples were hard and jutting out against the thin material. Her long legs were spectacular underneath the red material. She stood there, apparently enjoying the dumbfounded look on my face. Lisa slowly turned around so I could see all of her body. The teddy lifted up in the back as she turned, exposing her magnificent ass. My cock was pushing against my shorts as it grew. When she was facing me again I looked at her pussy. Her pubic hair was shaved into a narrow landing strip and neatly trimmed.

"Do you like it?"

I could barely stammer I love it.

She walked over to me with a sexy swaying motion and kissed me lightly on the lips. I reminded myself to go slow, and let her take the lead tonight. I returned her kiss tenderly and cautiously put my arms around her waist. She felt wonderful in my arms. Her big breasts pushed against my chest and the kiss started warming up. I very slowly moved my hand up Lisa's back, over her bare shoulders and to the nape of her neck. She must have taken this as a positive move because she pressed herself against my body tightly and started exploring the tips of my lips with her tongue. In a matter of seconds our tongues and lips were dueling each other in a very passionate kiss. I thought, so much for slow, she is hot. My cock was already rock hard and it was pressing against Lisa's lower abdomen. I reached down and moved it into a more comfortable position then reached behind her and got a handful of her magnificent ass cheeks and pulled her tighter into my body. When we finally broke our first kiss, Lisa stepped backwards and pulled the teddy over her head and threw it on the floor.

She said, "I didn't put the bottom on to save us time."

She looked magnificent standing there, proud of her body, with a big grin in her face. I had to stare. As much as I wanted her I couldn't take my eyes off of that sexy body. She didn't want to waste anymore time so she yanked my shorts down in a flash, grabbed my very erect cock and said "let's fuck."

We got on the bed, Lisa flat on her back with her legs spread to accommodate me. This was not a time for foreplay for either of us. I remembered slowly, and fought the urge to slam my rock hard cock into her in one thrust. It had been more than twenty years since she had sex, and she was bound to be tight. I slipped a finger between her pussy lips to see if she was wet. I was surprised at the amount of moisture I found there. I pushed my finger up into her vagina and it was soaked too. So I moved over her and gently put the head of my cock against her pussy opening.

Lisa said "hurry up, I can't wait any longer."

Now I pushed the head of my cock into the opening and felt a lot of resistance. I was concerned I would hurt her so I stopped for a minute. I looked down at her face and saw no signs of pain so I pushed a little more cock into her. Lisa was getting very impatient. She wanted all of me, and told me that. When I didn't respond she slammed her hips upward into my groin in one fast move. I heard her gasp in pain, and her body tense up, so I pinned her to the bed with my body and lay very still, imbedded deep in her pussy. When Lisa started relaxing I slowly pulled my cock from the depths of her pussy then slid it back in. She was making little murmuring noises. The pain was gone from her face, replaced by a lustful look.

I hadn't had sex in almost a year, and Lisa is such a beautiful, sexy lady, and I was having trouble controlling my orgasm, but I wanted Lisa to really enjoy this first time. She was tight, but wet, and starting to loosen up. I sped up the pace a little and Lisa responded by starting to moan. Since I was not familiar with her reactions during sex I didn't know how to interpret the noise so I slowed down some. Lisa quit moaning, and asked me what was wrong. Nothing Lisa, I replied, and started stroking her fine pussy faster. The moaning started again, followed almost immediately by a big shuddering type vibration as Lisa started to cum. Her juices were pouring over my cock, and she continued to vibrate under me. That of course set off my orgasm. I started cumming deep inside of her and couldn't quit. I sprayed stream after stream of hot sticky cum deep into her pussy. My sperm added to Lisa's enjoyment as she continued to shake.

I wrapped my arms around Lisa and rolled us onto our sides. I was still buried in her cum filled pussy.

She pushed up against me as close as she could get and said, "Thank you Tom, I loved it."

We lay that way for awhile until Lisa got up to empty the cum from her pussy.

When she came back to bed she asked, "How long have you been saving that for me?"

We fell asleep in each others arms for the first time.

............................................................................................................

I awoke around 7 the next morning with Lisa asleep with her head on my chest. Both of us were nude and her big breasts felt good pressed against my body. I carefully removed the sheet that was covering us so that I could gaze at her fantastic body. Her long legs, the swell of her hip, her huge boobs, all looked very good in the morning light. Lisa must have known I was staring. She stirred a little, opened her eyes and gave me a big smile. Her hand moved down to my limp cock and gave it a gentle squeeze. Can I have some more of that this morning, she asked?

I would have asked her that question but she beat me to it. I asked her if she was sore from last night. She replied, no, it hurt for a minute then I was OK. I lazily started caressing her shoulder with my hand, and reached across my body to playfully squeeze her big tit. Lisa seemed to enjoy a light touch on her bare upper body, so I continued that with one hand as I slowly explored her body with the other. Lying on my chest as she was kind of limited the parts of her body I could reach, so I slid out from under her. She settled down on the king sized bed on her back leaving a lot of body for me to enjoy. I sat up and looked at this gorgeous lady from head to toe. Her breasts were flattened out from being on her back, but the nipples were sticking out and were hard. Her breath came in slow even rhythm as she watched me staring at her. Her pubic hair landing strip and sexy long legs completed a very hot picture.

I leaned over and kissed her on the lips. I kissed her softly at first, then with more pressure as she responded to my efforts. I broke the kiss so I could kiss the rest of her body. I moved to her neck and kissed her under her chin, behind her ear and down to her collarbone. She had a very sensitive neck. I slowly moved down to her left breast, with my tongue and lips tasting her skin for the first time. Lisa looked, felt and tasted wonderful. When I arrived at her breast I licked around the nipple, lifted her big breast up so I could run my tongue along the sensitive bottom, then opened my mouth and sucked in as much of her breast as I could. Lisa was starting to squirm under me, causing me to have trouble keeping all of that tit in my mouth, but I kept sucking. I then began circling her hard nipple with my tongue while I continued to suck. Lisa was getting very hot.

I slid my hand down to Lisa's lower abdomen and lightly moved my fingertips up and down the crevice where her legs met her body. Up and down one leg, across the top of her landing strip and up and down the other leg. Across her body to the other leg and do it again. Each pass I moved a little lower on her body until I was brushing her outer labia from top to bottom. The combination of my mouth and tongue on her breast and my fingers around her sex had Lisa almost ready to cum. She was squirming, and moaning. I decided it was time to fuck.

I moved between Lisa's long legs and pushed my hard cock up against her pussy lips. She gave me a big smile. I slipped the bulbous purple head of my cock into her opening. I was fearful that Lisa would still be tight, as she was last night. I watched her face for signs of pain as I slowly pushed my hard cock all of the way into her wet pussy. When I had bottomed out I could see no signs of pain on Lisa's face so I started to stroke her pussy with long measured strokes. Lisa responded by raising her hips against me in the same rhythm. As I went faster her breathing became a gasping for air and her orgasm hit her. I kept up my rhythm to make her orgasm last longer. When she came down from her natural high I kissed her again and told her that it was time to do a lot of different positions. She commented that I hadn't cum yet. I responded I'll get mine later, enjoy yourself.

I pulled my knees up under Lisa's thighs and grabbed her legs and put them up in front of me against my chest. She was now lying on the small of her back with her ass up against my thighs and her pussy still filled with my cock. She had a very inquisitive look on her face until I started to pump my cock deep into her sopping wet pussy. I could see all of her hot body and reach it too, while we fucked. I reached down and softly caressed her breast as I pumped. With one hand I found her nipple and rolled it between my thumb and forefinger. Lisa started that moaning sound that I was beginning to love to hear her make, so I moved my other hand down to her pussy lips to get my finger wet. I found her clit and massaged it with my wet finger while I played with her nipple and pumped my cock deep in her vagina. The moaning intensified and her orgasm started building again. I pulled almost all of the way out of her tight love tunnel, and then I plunged back in again. The second time I pulled out she started to spasm and when I pushed all of the way back in her orgasm exploded. She was shaking real hard and moaning loudly. This one was much stronger than the first one and I had trouble holding her in this awkward position, which I wanted to do to prolong her orgasm. I remained motionless until her pleasure subsided

When Lisa had control of herself again I turned her on her side, without removing my still hard cock from her pussy, and rolled around behind her. I gently lowered us both to the bed. Now I was buried in her pussy while lying behind her on the bed. This position allows me to play with all of Lisa's goodies and I can control my own climax. I resumed the slow stroking of her pussy and played with her tits. We both felt relaxed and Lisa calmed down after her big orgasm. I moved my hand from her tits to between her legs, and gently caressed the outside of her labia. Lisa began to move slowly, in time with my cock pumping in her pussy. When she seemed to be getting back into the excitement of good sex I rolled over onto my back, pulling her with me, so that now she was on top. I suggested that she sit up and enjoy the ride.

Lisa sat up on my rock hard shaft, with her back facing me, and started to ride me in reverse cowgirl style. Her toned body was bouncing up and down on my thighs at a very rapid pace. I felt my orgasm starting to build deep inside me. I asked Lisa to turn around so I could suck het tits while we fucked. Lisa slowly turned around to face me, never letting my cock leave her warm, wet pussy. I had to have one of those long, hard nipples in my mouth so I sat up, leaned over and sucked the left one in. I used my tongue to circle the hard stub. Lisa immediately started to moan and shiver. I knew she was close to another orgasm so I pumped my hips up at her furiously. Lisa could not hold back the loud "Oh my God" that escaped her throat as she climaxed. Her juices flowed over my cock and balls and onto the bed soaking me and the bed. This orgasm kept flowing as Lisa let out a continuous low wail and shook from head to toe.

All of her noise and movement set off my orgasm. I let go of Lisa's breast as my semen started spurting out the end of my cock. Stream after stream of cum flew into Lisa. She kept cumming and jerking as it filled her vagina. She could no longer support herself so I lay down on the bed and lowered her gently on top of me. We lay like that for a couple of minutes as her big climax slowly subsided.

When Lisa finally recovered she sat up on the bed, took one look at my now limp cock and said I need to properly thank you for that one. She lowered her head to my shrinking penis and began to lick and suck it clean. What a great feeling. Her warm, wet tongue and soft lips kept me in heaven. Slowly and lovingly she licked and sent tingling feelings up and down the length of my cock. When she finished there was not a speck of her fluids or my cum on my cock. When she came back from the bathroom, still nude, she said "how about some breakfast."

rafters11
rafters11
109 Followers
12