Cheering Up A Friend Ch 01

This story is the first in a series. The first chapter was supposed to chronicle the entire first night, but I decided to break it into two parts. Chapter 2 will follow shortly.

As a writer, I thrive on feedback. Hearing what you like or don't like about my story is the only way I know whether what I'm doing is any good. So, PLEASE give me some. HOWEVER, don't waste your time if you are writing to say that you don't like this "type" of story. If that's all you have to say, then why are you even reading stories in this section of Literotica. Also, don't waste your time telling me about social values or morals. This is fiction (maybe)...read it as such. It's meant for fun. So, with that said, "enjoy"...

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My name is James and I'm 38 years old. I met my wife, Lisa, when she was 16. I, being one year older, was a senior in high school. It was truly love at first sight. From day one, we were inseparable. We experienced many firsts with each other and within a year, we lost our virginity to each other. Within three years, we were married. We went to college together, got settled down, and bought a house in the country. We've now been married 17 years.

I have a decent sales career. She works second shift as a supervisor at a local factory. Between us, we make enough money to have a large house with all the toys one could want, including a giant in ground pool. Our house is far removed from our neighbors; which suits us just fine—lots of privacy.

My best friend, Matt, and I go back to grade school. We have been the closest of friends all through life. We each were best man in the other's wedding. With our wives, the four of us became a great group. We hung out together all the time. I've watched their two children grow up. It's been great, because we are so close that we are almost like second parents to them, but at the end of the day they went home.

Over the years, there was playful flirting amongst the four of us. It never went further than a wandering hand or dirty talk, but we all enjoyed it. Often, it got my wife and I excited and we would have great sex after they left. I can only assume that they did the same when they got home.

Things started to change over the last year or so. Matt's wife started to drink more and more. Not really sure why, but it got to the point that Matt couldn't take it anymore and he left her. That really pissed her off and the divorce that followed was very ugly. We sided with Matt and rarely see his ex anymore. In the months that followed, Matt became more and more depressed and lonely. His 14-year-old daughter stayed with her mom. And in the first few months, his 17-year-old son did too, but has since moved in with Matt.

Matt was moping around and really down. He spent a lot of time by us, but nothing seemed to pull him out of his hole. One night, lying in bed after sex, my wife and I were talking. The conversation turned to Matt. I wondered out loud how long it had been since Matt was with a woman. We figured it must have been close to nine months. I suggested to Lisa that maybe we should try to cheer him up with a threesome. I was half-joking, but half-serious, curious as to what her reaction would be. She thought for only a moment and said that she thought that it sounded like a great idea.

We talked some more over the following days. After we were both sure that it was okay with both of us, we started to put a plan together. We decided that the following Saturday when he came over, she would make a move on him and see how far things went. I told her that she was free to do anything she wanted with him. We also set a rule that at anytime, if one of us got uncomfortable with it, we would stop immediately. With that, the countdown to Saturday began.

The week seemed to fly by and creep along at the same time. We didn't have sex that week, although we did have a mutual masturbation session; which was not unusual for us on Thursday. We went over the plans once again while we were in bed next to each other. I was stroking myself while she played with her favorite vibrator. By the time we were done going through the plans for Saturday, we both had great orgasms.

Saturday finally came. Matt came over as planned, unaware of what the night would bring. We watched a movie. I sat in my favorite recliner. Lisa and Matt sat at opposite ends of the couch. When it finished, Lisa said she was tired and was going to get ready for bed. There was some sports show on TV that Matt and I started to watch. A few minutes later, Lisa came out wearing a long t-shirt nightie. Matt had seen her in it before, so it wasn't a big shock. He glanced at her, but didn't take too much notice and turned back to the TV. If he had looked closer, it was obvious that something was different this time. She had nothing on underneath.

Lisa came over and kissed me goodnight, making sure to bend far enough to let the nightie ride up in back. If Matt would have looked, he would have gotten a bit of a show, but he was fixed on the TV. As Lisa turned to walk back toward the bedroom, I told her not to forget to kiss Matt goodnight. This caught Matt's attention. His head spun toward me, his face showing puzzlement.

Lisa straddled his lap, letting her shirt ride up slightly, and plunked her bare bottom on his lap. She grabbed his face with both hands and kissed him square on the lips. When she pulled back, Matt looked at me. I smiled with approval and nodded for him to continue. This time when Lisa kissed his lips, Matt kissed back. Tentatively at first, Matt kissed my 37-year-old wife. As he relaxed a little, he kissed back more passionately and soon there tongues met in a deep French kiss. With just a twinge of jealousy mixed in, I found myself getting turned on watching my wife make out with a man other than me for the first time in over 21 years.

After a few minutes, Lisa pulled back and slowly slid down Matt's athletic body. He had played football in college and has always kept himself in excellent shape. His 240 pounds fits perfectly on his 6'2" frame. Physically, he could easily keep up with men ten to fifteen years younger than him. Lisa ended up kneeling at his feet. Her finger snaked their way up to the waist of his jeans. Matt's eyes darted back and forth from Lisa to me, wondering what was about to happen and what I would do about it.

Lisa turned to me, "Shall I continue?"

"By all means," I replied. Then I shifted by gaze up to Matt, "Enjoy."

She unbuttoned his jeans, then, slowly slid the zipper down. As she pulled his jeans open, she revealed a pair of briefs that were being stretched tight by a growing bulge underneath. Ever so slowly, she dragged her nails across the outline of his cock, teasing him. Her fingers grasped the top edge of his briefs and pulled it outward, extending the material, so that only Matt, who was staring down at her, could she his cock. She paused, staring into his eyes for a long moment, then pulled his shorts down, exposing his cock to Lisa and myself.

His ex-wife had told my wife that he had a "nice one". Over the years, I had heard rumors of him being pretty big. However, I had never seen it. Lisa must have agreed with his ex-wife, because the first word out of her mouth was, "nice!" His cock stood straight up. We would find out later that it was 8 ½" long. It was also pleasantly thick. Not freakish, but strong and powerful looking. The head was nicely shaped and in perfect proportion to his shaft. Below, two large balls hung loosely, not grossly huge, but, for lack of a better term, manly-looking. His entire pubic area was cover with a soft matte of brown hair. Just enough, my wife has since described it.

Lisa wrapped both her small hands around it, leaving the head showing. Gently, she slid them up and down, the tip of his cock disappearing into her fists only to reappear moments later. About the fifth or sixth time it appeared, Lisa leaned forward and kissed the tip of his cock. The next time it came back into sight, her tongue met it. She paused to flick the tip of her tongue across the head and around the opening, then, pulled her hands back up. As she repeated this, Matt put his arms on the back of the couch and laid his head back with his eyes closed. Realizing that we had planned this "attack" on him, he lost himself in the moment.

I crossed the room and grabbed my wife's lone article of clothing, pulling it over her head to reveal her body to my friend. He had seen her in skimpy bikinis before, but as his eyes opened he saw all that her body had to offer for the first time. Her 34A breasts with their tiny nipples planted above her flat stomach. Toned from the years of exercising she has done. Beneath that, the small triangle of dark brown pubic hair, sharply contrasted to her pale skin. Trimmed neatly and shaved on the sides, it pointed the way down to her cute little pussy, all neatly tucked away. She stood there for a few moments, letting him soak in her beauty. She had the body and face of a woman 15 years younger than her. Matt grinned his approval. As he reached for her, she pushed his hands away, sitting him back against the couch. His arms returned to the back of the chair as Lisa retook her position between his legs.

Instead of returning to my chair, I sat at the end of the couch to get a much better view. Lisa leaned down and kissed first one testicle, then the other. Her tongue wandered across the hills and valleys of his scrotum as her hand stroked his long cock. Finally, after several tantalizing minutes, her tongue danced up the side of his cock, pausing to run a circle around the head, then flicked its way back down the other side. The next trip up, her tongue tickled the ridge up the underside of his cock. This time, she took the entire head into her mouth, sucking slowly while running her tongue all around.

From years of practice, Lisa is excellent at sucking cock. She let the tip of his penis pop from her mouth, then, pulled it downward while letting her tongue slide down the topside of his shaft. Holding his cock gingerly in her hand, Lisa then began making long slow licks up and down all sides of his cock. Fast enough to make Matt squirm slightly in the chair, but slow enough to be a tease. She continued this for several long minutes as Matt's eyes rolled back into his head. I was in a trance watching her attending to this strange new cock. She played with it enthusiastically, like a child with a new toy.

Suddenly, without warning, she plunged his cock as far into her warm sweet mouth as she could. The length and girth did not allow for full penetration, in fact, she probably didn't get much more than half of it into her mouth, but as she bobbed her head on Matt's huge cock, her hands took care of the parts that were neglected by her mouth. One hand stroked the remaining shaft in rhythm with her mouth. The other hand gently grasped and squeezed his balls, rolling them in her hand, pulling them down away from his body.

As her intensity picked up, so did Matt's breathing. Involuntarily, his hips begin to thrust upward. Lisa hung on, trying hard to maintain the pace of her sucking while not choke on the biggest cock she'd ever sucked. I was frozen, sitting motionless, in awe of the cock and blowjob being given in front of me. I was hard as a rock inside my pants, but made no move to touch myself for fear of interrupting the moment.

Matt shouted a warning, "I'm cumming." This caused Lisa to pull back slightly with her mouth, but clamp on tightly while stroking firmly and deliberately up and down Matt's thick shaft. She flinched slightly when the first blast of his orgasm must have squirted into her mouth. I could see her swallowing rapidly as Matt's body shook as he continued to cum. My wife diligently worked to swallow every drop. When finally Matt's orgasm subsided, Lisa pulled back, gasping for air. "Holy shit was that a lot of cum."

Matt smiled down at her. "Sue never would let me cum in her mouth. Not once in the 18 years we were married. Thank you."

"My pleasure," Lisa replied. "You must have been saving that for awhile."

"Or maybe it was just the best blowjob I've ever had." Matt said. He tucked himself back into his pants and started to zip them up.

"What do you think you're doing?" Lisa questioned Matt. "We're not done yet. Why don't you guys meet me in the bedroom."

Matt and I both grinned as we watched her cute little round ass disappear down the hallway.