Titus
03-03-2020, 05:55 PM
Tiffany and I married young after she got pregnant with our one and only child. I was the highschool jock and she was my homecoming queen.
Fast forward twenty-two years. I run my own successful business. I would like to say I am still in jock shape but that would be a lie. I definitely sport a “dad bob” now. Complete with my middle aged belly bulge and receding hair line.
Tiffany on the other hand is better looking now than she was all those years ago. She is 5’8” with a body to die for. Full sized breast with a small waist line and wide hips.
She was always the perfect wife and mother. Wet conservative in her views and how she presented herself by the way she dressed.
She was a high school teacher. My daughter used to tease her about all the high school guys rating her as the top milf at their school. Our daughter stopped bringing new boy friends home because they all went goofy after meeting Tiffany.
Tiffany would always tell us we were imagining things or making things up. I assured her most of my guy friends were affected the same way. She would just tell me and my friends were all perverts.
That was a fact I couldn’t argue with. But there was another fact that presented itself. Tiffany started to dress a little more “progressively”. Her dresses were getting a little shorter. Her hair style less old school.
I started to have fantasies about her being with other men. But I knew bringing something like that up to her wouldn’t be received very well.
I had to come up with a different tact. I knew the only way to remotely have a chance of realizing this new “obsession”. Was it had to happen organically, from outside influences.
I talked to my best friend Chad about it. He told me I was crazy. But, didn’t hesitate to be “the guy”. I told him I would be cool with it but she would suspect I put him up to it and it wouldn’t work, as he was one of my pervert friends.
Enter Kyle, Chad’s seventeen year old high school senior son and one of Tiffany’s students. Kyle reminded me of me when I was his age. He was tall and fit as well as the quarterback for his school team. I used to tease Chad that he was my kid and not his. Chad is short and stocky with muscular build but his own dad bod belly.
Chad told me Kyle and his buddy’s often talked about Tiffany in a non-platonic way. That’s when I came up with my plan. We took Kyle out fishing one weekend. I made a story about having some medical issues that were causing me to have some man issues.
Chad played along being the sympathetic friend. Then in passing I mentioned how it was impacting my marriage. How it was hard on Tiffany as she really enjoyed sex. Kyle stayed quiet the whole time but listened intently.
A few days later Tiffany came home perplexed. Telling me Kyle had approached her asking for additional help with his studies. It shocked her because he was the stereotypical jock that normally did just enough to get by.
She offered to stay after school to help. But that would work because he had practice. She offered to meet him at school on Saturdays but that was game day.
He asked her if he could come by our house on Sunday’s. Kyle wasn’t an Einstein but he knew that his dad and I golfed on Sundays. So that put me out of the house for hours.
I asked her if she agreed to help him on Sundays. She told him she would have to talk to me first. I told her she should do it as I would be out until late afternoon anyway. I added Kyle surely could use the help.
She seemed to hesitate. I knew she was wrestling with the appropriateness of being alone with a student. My heart stood still for a long moment. Then she finally said she would do it. But added that Kyle better not waste his or her time. I silently hoped he wouldn’t either.
The next part of the plan was installing hidden cameras in key places. That was easy enough as I worked mostly from my home office. I had the living room, kitchen, dining room and of course all three bedrooms covered. I was pleased with my handy work. I was sure she would never find the cameras.
That first Sunday Tiffany had on her usual sweat pants and tee shirt lounge around the house clothes. But she also had her hair in a long single braid which made her look even younger. She also had on a light amount of make up. Which she normally abandons on the week ends unless we go out.
She seemed a little nervous but tried to hide it. I went through my normal ore golf routine. I greeted Kyle at the door on my way out. He was sporting a fresh hair cut and his cheeks flushed a little as he asked if it was ok for him to get the school help. I assured him it was and left him to it.
I shot my worse round of golf as did Chad. We talked about what might or might not be happening at my house. I was positive nothing would happen the first time, if ever.
Chad was selfishly hoping something would happen as it might open the door for him. His wife Mary was a real life”battle-axe”. She had really let herself go over the years. Chad’s sex life was anemic unlike mine.
Tiffany and Mary had been best friends in high school as well, but had a falling out years before. Tiffany has tried on more than on occasion to repair the relationship. Mary refused and made it worse with her somewhat obnoxious personality by gossiping.
Kyle was gone by the time I got home. Tiffany was grading papers at our kitchen island. She seemed a little flustered when I got home. She asked me how golf went. I wanted to say like shit because all I could think about was her fucking my best friends teen age hunk of a son. Instead all I said was I have shot better.
I asked her how her session went with Kyle. She stuttered out that it went ok. She was pleased that he seemed serious about doing better on his school work and exams.
She immediately changed the subject asking me to give her some time to finish grading before we went out to dinner. I left her to it as I went to shower. I was dying to see what was on the videos but knew I would have wait until tomorrow morning hen she was at work.
We went to dinner and she had a second glass of wine which was unusual. I brought up Kyle again saying I was glad he wasn’t solely relying on getting an athletic scholarship now and taking school more seriously. I teased her that he was probably one of those guys our daughter used to talk about that had a crush on her.
Tiffany did rebuke me and I took that as a good sign. She just told me not to be silly. Kyle seemed very genuine about getting better grades.
That night we had some pretty hot sex. Something else we typically didn’t do on a Sunday night. Monday she had to be at school earlier for pre class meetings. I was usually beat from golfing earlier. She actually initiated the sex and was aroused enough she wanted to skip the usual foreplay it took to get her fully in the mood.
I took that as another good sign that Kyle was having a positive affect on her. I could barley sleep wanting to check the video.
As soon as her car cleared our driveway I was at my desk accessing the video from the day before. They set up at the kitchen island sitting a good distance apart. Their conversation seemed strained at first and all over the map. The weather, his upcoming game, some movie I had never heard of.
They finally got into the class work. As they got more comfortable they did move to sit closer to each other. Kyle seemed to blush more as they talked and Tiffany giggled like a school girl.
Finally, after a long while they closed the books. Tiffany made them some lunch and they just talked. Tiffany asked him if he missed not hanging out with his girl friend and friends to get tutored on his only day off.
He smiled telling her had broken up with his girl friend when he found out she stopped using birth control. That straightforward and very personal reply caught Tiffany off guard. She quickly moved from her stool and started to clean up the lunch dishes.
Kyle apologized if he had said something wrong. I could see Tiffany visibly gather her thoughts working herself back into teacher/mentor mode. She told Kyle she wasn’t upset. She told him he had made a responsible decision. But a more responsible decision would be to wait at least after he graduated high school to have sex.
Kyle laughed saying that would have been good advice a year or so ago. But that train had left the station and it would be to hard to call it back. I wasn’t sure but I swear Tiffany’s nipples were poking through her tee shirt.
There was another long awkward pause before her phone rang breaking the silence. She told Kyle it was our daughter and she had to take it. She said she would see him around school and again next weekend.
He gathered his things and let himself out. Tiffany answered the phone and it was our daughter. I silently cursed wondering if she inadvertently cock blocked Kyle.
Now I understood why she was so horny that night...
I talked to Kyle's dad a couple days later. He told me Kyle was walking on cloud nine about something. He was sure something would happen between them. I wasn’t as certain but I was very hopeful.
Tiffany doted over me the next couple days and again initiated sex by joining me in the shower. We hadn’t done that in years. I half expected she may have felt guilty for having carnal thoughts about Kyle. I wasn’t sure if my fantasy would be realized. But something was definitely happening with her.
We went to the high-school game that next Saturday, something we did every Saturday. However, it was normally in the capacity of ticket sales and concessions. Tiffany didn’t like football that much and our daughter had not been a cheerleader in a few years.
This time we sat at the fifty yard line and she excitedly cheered her team on, often yelling Kyle's name when he made a good play. Another great sign that things were progressing favorably.
Sunday couldn’t come fast enough. Again I passed Kyle on the way out of the house. I congratulated him on the big win. He thanked me before going inside. My heart was racing with both hope and nervousness.
Again I lost money playing golf. Usually I won most of the time and my golf buddies chided me about being off my game. Chad and I looked at each other both thinking the same thing.
When I returned this time. I could tell by how fidgety Tiffany was that something happened. It fucking drove me crazy. I wanted to check the video so bad.
She told me she wasn’t feeling well and asked if I could just order out. She wasn’t hungry and just wanted to lie down.
I panicked thinking something might have backfired. Having a vision of Kyle trying something and Tiffany freaking out. Tiffany went upstairs. I barely ate a bite of my dinner.
I went to bed half expecting to see an ugly scene on the video the next day. Tiffany was restless the whole night and was visibly tired the next morning before heading off to work, barely saying a word to me.
After she left I bolted to my office. Like last week Tiffany had her hair in a long single braid. She had on some sweat pants but not her loose fitting ones like last time. Her tee shirt was more form fitting as well.
Kyle set his things down on the kitchen island. He asked her if she enjoyed the game. She replied she did very much asking him how he knew she was watching. He smiled telling her she was as loud as his mother. Tiffany apologized telling she just got caught up in beating our longtime rivals.
She told him he played very well. He caught her off guard saying seeing her cheering in the stands made him want to play better. She laughed telling he was being silly. Adding she was just his old teacher. Kyle laughed out loud telling her that she was the hottest teacher ever. Again Tiffany rebuffed him playfully. Telling him to open his books. The flush of her cheeks didn’t go unnoticed.
She sat next to him as they went over his school work. She would give home something to work out and move off to throw some laundry in the wash or something else. Kyle's eyes were glued to her ass every time she got up.
One particular time she got up to rinse off the breakfast dishes. Kyle slipped off his stool sneaking up behind her. I was mesmerized not realizing I was hold my breath.
Like a cobra Kyle snatched the water wand from Tiffany. Holding her with one muscular arm pressing her against the cabinet. He doused her with water causing to scream out for him to stop.
Was this the moment things went south? He continued to soak her and himself as well. Her screams turned into hysterical laughter. He finally stopped when she got some in her mouth and choked a little.
They stood facing each other completely soaked. She told him he was crazy and what possessed him to do it. Without warning Kyle kissed her. Tiffany immediately pushed him away and slapped him across the face.
I thought of fuck this was bad. She yelled at him this time seriously. Telling him how inappropriate what he just did was. I expected Kyle to turn and bolt for the front door.
He apologized for upsetting but that he thought she was beautiful. She told him he should leave. This was it the end of my fantasy. Kyle grabbed his things and moved off camera into the dining room.
Tiffany looked completely bewildered but only hesitated a second before following after him calling his name. I switched to the other camera fast forwarding to where Kyle enter the dining room. He froze as Tiffany called his name. Turning to face her she walked up to him.
She took his things and let them drop to the floor. She went up on her toes and kissed him deeply. I fucking saw rockets. My heart was zooming as I watched what I hoped was my dream come true.
Tyler reached for the hem of her shirt helping her get the wet thing off. Her nipples were fully erect a combination of the water and her arousal. Kyle leaned down to suck and lick each one. Her head went back as she moaned with pleasure.
She lifted his head and kissed him again passionately as she wrestled to get his wet shirt off. After tossing it aside she rubbed her hands over his ripped chest and abs then licked and bit his nipples as she worked his belt lose.
I had to release my now hard cock and could only stroke it slowly as I was already on the verge of cumming.
His pants went to the floor and she followed them down kneeling in front of him. I had to admit a tinge if jealousy went through me for just a moment. We were about the same thickness but he had to be at least ten inches long. He was definitely a couple inches longer than me.
My jealousy faded as she feverishly stroked his ass as she sucked him or licked his balls. Their eyes remained locked together as she looked up at him while on her knees.
Kyle pulled her up to her feet. Her spun her around to face our table. He pulled her pants down and she eagerly stepped out of them. He pushed her forward so her hands rested in the table while pulling her lower body back.
He went to his knees and planted his face in her ass . Tiffany let out a gasp and a long moan. I had to admit his saviness at how to pleasure a woman was impressive at such a young age.
She went up on her toes and her hand went back to his head as she hissed telling him she loved having her pussy and ass licked.
The next thing she said forced me to squeeze my cock to keep from shooting my load. She told him to fuck her!
Kyle stood up and started to work his now rock hard upturned cock with a large head into her willing pussy. He was having a little trouble. Her hand shot down as she guided him inside of her.
She let out a very loud moan as he sank all the way in. He gave her just a moment before he started to fuck her. It was amazing watching them as her heavy tits swung as he fucked her and she pushed back towards him.
She moaned again when his hands moved to her tits as he continued to fuck her deep. Tiffany came and her legs buckled. Kyle kept her steady, she turned towards him and the kissed again. She sat up on the table pulling her knees up and legs wide.
Kyle licked her pussy a couple times causing her to gasp and arch her back. He stood and pushed his cock back in. This time he fucked her hard so she had to hold onto the table's edge.
Tiffany arched up again and her eyes rolled up in her head. She yelled his name as she came again. Kyle was panting wildly by this time. He asked her where she wanted him to cum. Without the slightest hesitation she yelled for him to cum inside of her.
That was it I tried to hold off but came all over myself. I sat there breathing heavily as he emptied his young balls into my wife’s pussy as she gripped his muscular arms and watched his cock sliding in and out. He fell forward on top of her as she locked her legs around his back.
He finally pulled out and helped her off the table, they kissed some more. She told him he was amazing but he needed to leave before I got home.
Kyle dressed and she walked him to the door still naked. She gave him a long goodbye kiss. After he left she sagged back against the door. I heard her say “Oh fuck what just happened.”
She went off to shower and I came home about an hour later. So what she was feeling was probably guilt about cheating and scared that she had just had sex with one of her students. I could see how that may may make her feel ill.
Over the next couple days she was about the same. She seem distracted and went to bed early claiming to be ill. I needed to find a way forward. Things didn’t look good when she said she wasn’t feeling well enough to tutor Kyle the next Sunday.
I went to Clay for an idea what to do next. He suggested we bring Kyle in on everything. At first I didn’t think it was a good idea. But Clay said Kyle was moping around as well. Clearly bummed that Tiffany had made excuses why he couldn’t go over again.
He thought Kyle needed to understand it could only be sex and nothing more. Explaining that if Kyle knew we had set this up under the pretense of helping her and I with my “condition”, he would know that we knew. We could then make him understand she wouldn’t see him anymore if she felt guilty about cheating. It sounded logical but I wasn’t sure it would help. But I didn’t have a better idea.
So we got Kyle out on the boat again and I brought up that I knew what happened between him and Tiffany. Of course he denied it at first until his father told him we both knew.
He was definitely afraid at first. I continued to let him believe I had a condition and that is why his dad and I put things into motion. But we wanted him to understand it was to be only sex. He was obviously confused at first. But after we explained to him it would have to be a one time thing if she thought there would be a risk of losing her marriage.
The power of good MILF pussy should never be under estimated. He did admit he was crushing on her bad. But he totally understood where we were coming from. But he was sure she wouldn’t have sex with him again. I smiled at him saying I think he was wrong. Thinking to myself no one should ever underestimate the power of a big young cock and a strong back.
Kyle asked his father if he thought his mother knew. Chad responded saying, “Boy we would both be at the bottom of this lake with cinder block slippers.”
Kyle asked me again if I was really ok with her having sex with someone else. I told him it wasn’t for everyone, but I was more than ok with it.
So I told him what we needed to do next. He was all ears. That next Thursday was the third such day of the month. Tiffany stayed late at the school to meet with parents by appointment.
She parked her SUV in the faculty parking lot on one side of the school in her own reserved slot. There were nearby places where one could conceal themselves with a perfect view of her car.
I parked on the opposite side of the school and made my way to a spot very close to her parked car but well hidden. She finally came out of the building she had just put her things in the back seat when Kyle pulled up on his motorcycle and stopped directly behind her car.
He asked her why she was avoiding him. She said she wasn’t but that she was just really busy. I could tell by her body language she was not sure what to do.
Kyle said he just wanted to talk to her. She initially told him she didn’t think it was a good idea. He promised her it was just to talk. He had received two separate scholarship offers and he wanted her advice. She tried to convince him to see her in the morning at school.
To his credit he didn’t give up. Tiffany looked around then told him to park his bike behind a nearby dumpster. He did as she asked then joined her in her car. There were no other cars nearby but she clearly looked around very nervous.
Kyle got into her car and pulled out some info on the two schools. They talked for a while I could make out most of it. She was telling him about the pros and cons of both schools. Both were a few states away and had different things to offer.
He finally settled on one. I think she expected him to get out of her car. He stuck to the script I had given him about understanding she had conflicted feelings about what happened. She told him it was wrong and her fault that it happened and he wasn’t to blame.
He said he understood, but he would be leaving in a few couple months to visit his mother's family back East. Then he was off to a football camp before heading to his new school early as well. He touched her cheek and said he just wanted to spend more time with her before he left.
Again she told him she couldn’t but she clearly was conflicted. He leaned in to kiss her and she pulled away. She told him she loved me very much and didn’t want to lose me. That was self assuring news. Kyle said he understood and just wanted what she would be willing to give him.
She looked at him without saying anything for a long moment. Then pulled his face to her and kissed him. In a flurry of flying clothes her dress came over her head as he moved to take his pants and shirt off.
They clumsily moved to the back of her large SUV. I could see her head moving up and down. After a short while the swapped an one of her legs hooked the front passenger head rest with the other over the back seat.
I could see his broad back and the back of his head. Tiffany was moaning steadily as he ate her pussy until she came with a shout. He sat up on the seat and she straddled him. There was enough light from a spotlight on the corner of the building that I could see he was feasting on her tits.
She raised up then lowered herself down, letting out a long slow moan. Moments later she was bouncing up and down on his young magical cock. At one point she had both hands braced against the roof of the car as she rode him to a screaming orgasm.
Kyle wasn’t finished even though she begged him to give her just a minute. He flipped her on her back and moved on top of her. Her protest died and was replaced with her yelling yes over and over again. She begged him not to stop fucking her. I heard him ask her if this was his pussy until he went off to school. She didn’t hesitate answering he could have her pussy anytime he wanted.
That was it she was hooked. Kyle fucked her furiously in the back seat. Her legs were flailing in the air as his ass went up and plunged back down. She was moaning screaming and grunting with every stroke. She came again and her feet were up in the air shaking like she was having a seizure. Kyle let out a yell as he came inside of her.
They laid there talking for a long time. I left them to it and rushed back home. She came in and immediately showered. She was clearly nervous yet very talkative.
I hoped Kyle had said everything I told her verbatim. She was clearly restless so I asked her if everything was ok. She asked me if I still had those fantasies about her having sex with other men. I stopped reading my book and asked her if that was a trap question.
She told me it wasn’t but just wanted to understand why I would be ok with something like that. I explained it to her honestly. That it didn’t mean I didn’t love her anymore. I just was very turned on by the idea of her being pleasured by someone. Addendums as planned that so many other people do it behind their partners back and that usually ends badly.
There was a momentary look of panic on her face. I realized technically she had cheated on me. But in all fairness she was entrapped be me. I was sure she had never done anything like this before.
I asked her if she would consider trying it at least once. I was ok with her next lie. She told me that my best friends son and her student Kyle was constantly flirting with her.
I asked her if she thought about having sex with him. She didn’t technically lie when she admitted she did. Even though she had already fucked him twice already.
She asked me if I wanted her to seduce him. I immediately told her I would love her to do it. She asked me again if I was sure. I placed her hand on my hard cock.
We fucked like crazy that night with me saying things like, "I have seen Kyle in the men’s locker room and he had a big cock." She came almost immediately on my own cock. Obviously she was thinking about feeling him deep inside her again soon.
Kyle showed up on the next Sunday. Headed of to golf as before. I had showed Tiffany the recently installed camera in our bedroom. I told her I put it there just that Saturday.
When I got home from golfing, she definitely had a just well fucked glow about her. Her hair was down and her lipstick still smudged. She was wearing a robe as she led me upstairs. The bed was a wreck and the room smelled of sex.
She asked me if I was ok. I kissed her, surprised at the taste of what surely was cum in her mouth. We took a quick shower together. I got my laptop and we watched the movie together.
They were both already naked when they entered our bedroom. I watched them kiss and get into a sixty nine with her on top. I loved watching her worship his young cock with her lips and mouth as her ass wiggled over his face.
They fucked in multiple positions with him cumming in her fucking her from behind. She deftly stroked my cock as we watched. The look of sheer lust on her face was amazing.
They cleaned up and talked for a while. She started sucking his cock again and soon he was really fucking her hard. He finally let her on top where she rode him until he told her he was going to cum. She climbed off his cock which was lathered up with her juices.
He let out a moan as sucked him like a mad woman. He warned her he was about to cum she only sucked and stroked him with more urgency. Until he yelled out “Ohhhhh fuck me!!!!!”
He came in buckets but only a little descaled her mouth. He went limp and she moved up his body and kissed him probably giving him his first taste of his own cum.
She sent him on his way, promising him to see him again soon. The video ended and I rolled on top of her. She eagerly pulled me inside of her already wet pussy. I didn’t last very long but that was ok.
We talked late into the night. She was convinced I wanted this and she admitted it was amazing for her as well.
Kyle was her regular fuck buddy until he left town. He would fuck her more when he was home during the holidays. I would always get to watch them later. A few times I had watched them in person which was even better than on video.
Hope you enjoyed this story....Part two soon.
Fast forward twenty-two years. I run my own successful business. I would like to say I am still in jock shape but that would be a lie. I definitely sport a “dad bob” now. Complete with my middle aged belly bulge and receding hair line.
Tiffany on the other hand is better looking now than she was all those years ago. She is 5’8” with a body to die for. Full sized breast with a small waist line and wide hips.
She was always the perfect wife and mother. Wet conservative in her views and how she presented herself by the way she dressed.
She was a high school teacher. My daughter used to tease her about all the high school guys rating her as the top milf at their school. Our daughter stopped bringing new boy friends home because they all went goofy after meeting Tiffany.
Tiffany would always tell us we were imagining things or making things up. I assured her most of my guy friends were affected the same way. She would just tell me and my friends were all perverts.
That was a fact I couldn’t argue with. But there was another fact that presented itself. Tiffany started to dress a little more “progressively”. Her dresses were getting a little shorter. Her hair style less old school.
I started to have fantasies about her being with other men. But I knew bringing something like that up to her wouldn’t be received very well.
I had to come up with a different tact. I knew the only way to remotely have a chance of realizing this new “obsession”. Was it had to happen organically, from outside influences.
I talked to my best friend Chad about it. He told me I was crazy. But, didn’t hesitate to be “the guy”. I told him I would be cool with it but she would suspect I put him up to it and it wouldn’t work, as he was one of my pervert friends.
Enter Kyle, Chad’s seventeen year old high school senior son and one of Tiffany’s students. Kyle reminded me of me when I was his age. He was tall and fit as well as the quarterback for his school team. I used to tease Chad that he was my kid and not his. Chad is short and stocky with muscular build but his own dad bod belly.
Chad told me Kyle and his buddy’s often talked about Tiffany in a non-platonic way. That’s when I came up with my plan. We took Kyle out fishing one weekend. I made a story about having some medical issues that were causing me to have some man issues.
Chad played along being the sympathetic friend. Then in passing I mentioned how it was impacting my marriage. How it was hard on Tiffany as she really enjoyed sex. Kyle stayed quiet the whole time but listened intently.
A few days later Tiffany came home perplexed. Telling me Kyle had approached her asking for additional help with his studies. It shocked her because he was the stereotypical jock that normally did just enough to get by.
She offered to stay after school to help. But that would work because he had practice. She offered to meet him at school on Saturdays but that was game day.
He asked her if he could come by our house on Sunday’s. Kyle wasn’t an Einstein but he knew that his dad and I golfed on Sundays. So that put me out of the house for hours.
I asked her if she agreed to help him on Sundays. She told him she would have to talk to me first. I told her she should do it as I would be out until late afternoon anyway. I added Kyle surely could use the help.
She seemed to hesitate. I knew she was wrestling with the appropriateness of being alone with a student. My heart stood still for a long moment. Then she finally said she would do it. But added that Kyle better not waste his or her time. I silently hoped he wouldn’t either.
The next part of the plan was installing hidden cameras in key places. That was easy enough as I worked mostly from my home office. I had the living room, kitchen, dining room and of course all three bedrooms covered. I was pleased with my handy work. I was sure she would never find the cameras.
That first Sunday Tiffany had on her usual sweat pants and tee shirt lounge around the house clothes. But she also had her hair in a long single braid which made her look even younger. She also had on a light amount of make up. Which she normally abandons on the week ends unless we go out.
She seemed a little nervous but tried to hide it. I went through my normal ore golf routine. I greeted Kyle at the door on my way out. He was sporting a fresh hair cut and his cheeks flushed a little as he asked if it was ok for him to get the school help. I assured him it was and left him to it.
I shot my worse round of golf as did Chad. We talked about what might or might not be happening at my house. I was positive nothing would happen the first time, if ever.
Chad was selfishly hoping something would happen as it might open the door for him. His wife Mary was a real life”battle-axe”. She had really let herself go over the years. Chad’s sex life was anemic unlike mine.
Tiffany and Mary had been best friends in high school as well, but had a falling out years before. Tiffany has tried on more than on occasion to repair the relationship. Mary refused and made it worse with her somewhat obnoxious personality by gossiping.
Kyle was gone by the time I got home. Tiffany was grading papers at our kitchen island. She seemed a little flustered when I got home. She asked me how golf went. I wanted to say like shit because all I could think about was her fucking my best friends teen age hunk of a son. Instead all I said was I have shot better.
I asked her how her session went with Kyle. She stuttered out that it went ok. She was pleased that he seemed serious about doing better on his school work and exams.
She immediately changed the subject asking me to give her some time to finish grading before we went out to dinner. I left her to it as I went to shower. I was dying to see what was on the videos but knew I would have wait until tomorrow morning hen she was at work.
We went to dinner and she had a second glass of wine which was unusual. I brought up Kyle again saying I was glad he wasn’t solely relying on getting an athletic scholarship now and taking school more seriously. I teased her that he was probably one of those guys our daughter used to talk about that had a crush on her.
Tiffany did rebuke me and I took that as a good sign. She just told me not to be silly. Kyle seemed very genuine about getting better grades.
That night we had some pretty hot sex. Something else we typically didn’t do on a Sunday night. Monday she had to be at school earlier for pre class meetings. I was usually beat from golfing earlier. She actually initiated the sex and was aroused enough she wanted to skip the usual foreplay it took to get her fully in the mood.
I took that as another good sign that Kyle was having a positive affect on her. I could barley sleep wanting to check the video.
As soon as her car cleared our driveway I was at my desk accessing the video from the day before. They set up at the kitchen island sitting a good distance apart. Their conversation seemed strained at first and all over the map. The weather, his upcoming game, some movie I had never heard of.
They finally got into the class work. As they got more comfortable they did move to sit closer to each other. Kyle seemed to blush more as they talked and Tiffany giggled like a school girl.
Finally, after a long while they closed the books. Tiffany made them some lunch and they just talked. Tiffany asked him if he missed not hanging out with his girl friend and friends to get tutored on his only day off.
He smiled telling her had broken up with his girl friend when he found out she stopped using birth control. That straightforward and very personal reply caught Tiffany off guard. She quickly moved from her stool and started to clean up the lunch dishes.
Kyle apologized if he had said something wrong. I could see Tiffany visibly gather her thoughts working herself back into teacher/mentor mode. She told Kyle she wasn’t upset. She told him he had made a responsible decision. But a more responsible decision would be to wait at least after he graduated high school to have sex.
Kyle laughed saying that would have been good advice a year or so ago. But that train had left the station and it would be to hard to call it back. I wasn’t sure but I swear Tiffany’s nipples were poking through her tee shirt.
There was another long awkward pause before her phone rang breaking the silence. She told Kyle it was our daughter and she had to take it. She said she would see him around school and again next weekend.
He gathered his things and let himself out. Tiffany answered the phone and it was our daughter. I silently cursed wondering if she inadvertently cock blocked Kyle.
Now I understood why she was so horny that night...
I talked to Kyle's dad a couple days later. He told me Kyle was walking on cloud nine about something. He was sure something would happen between them. I wasn’t as certain but I was very hopeful.
Tiffany doted over me the next couple days and again initiated sex by joining me in the shower. We hadn’t done that in years. I half expected she may have felt guilty for having carnal thoughts about Kyle. I wasn’t sure if my fantasy would be realized. But something was definitely happening with her.
We went to the high-school game that next Saturday, something we did every Saturday. However, it was normally in the capacity of ticket sales and concessions. Tiffany didn’t like football that much and our daughter had not been a cheerleader in a few years.
This time we sat at the fifty yard line and she excitedly cheered her team on, often yelling Kyle's name when he made a good play. Another great sign that things were progressing favorably.
Sunday couldn’t come fast enough. Again I passed Kyle on the way out of the house. I congratulated him on the big win. He thanked me before going inside. My heart was racing with both hope and nervousness.
Again I lost money playing golf. Usually I won most of the time and my golf buddies chided me about being off my game. Chad and I looked at each other both thinking the same thing.
When I returned this time. I could tell by how fidgety Tiffany was that something happened. It fucking drove me crazy. I wanted to check the video so bad.
She told me she wasn’t feeling well and asked if I could just order out. She wasn’t hungry and just wanted to lie down.
I panicked thinking something might have backfired. Having a vision of Kyle trying something and Tiffany freaking out. Tiffany went upstairs. I barely ate a bite of my dinner.
I went to bed half expecting to see an ugly scene on the video the next day. Tiffany was restless the whole night and was visibly tired the next morning before heading off to work, barely saying a word to me.
After she left I bolted to my office. Like last week Tiffany had her hair in a long single braid. She had on some sweat pants but not her loose fitting ones like last time. Her tee shirt was more form fitting as well.
Kyle set his things down on the kitchen island. He asked her if she enjoyed the game. She replied she did very much asking him how he knew she was watching. He smiled telling her she was as loud as his mother. Tiffany apologized telling she just got caught up in beating our longtime rivals.
She told him he played very well. He caught her off guard saying seeing her cheering in the stands made him want to play better. She laughed telling he was being silly. Adding she was just his old teacher. Kyle laughed out loud telling her that she was the hottest teacher ever. Again Tiffany rebuffed him playfully. Telling him to open his books. The flush of her cheeks didn’t go unnoticed.
She sat next to him as they went over his school work. She would give home something to work out and move off to throw some laundry in the wash or something else. Kyle's eyes were glued to her ass every time she got up.
One particular time she got up to rinse off the breakfast dishes. Kyle slipped off his stool sneaking up behind her. I was mesmerized not realizing I was hold my breath.
Like a cobra Kyle snatched the water wand from Tiffany. Holding her with one muscular arm pressing her against the cabinet. He doused her with water causing to scream out for him to stop.
Was this the moment things went south? He continued to soak her and himself as well. Her screams turned into hysterical laughter. He finally stopped when she got some in her mouth and choked a little.
They stood facing each other completely soaked. She told him he was crazy and what possessed him to do it. Without warning Kyle kissed her. Tiffany immediately pushed him away and slapped him across the face.
I thought of fuck this was bad. She yelled at him this time seriously. Telling him how inappropriate what he just did was. I expected Kyle to turn and bolt for the front door.
He apologized for upsetting but that he thought she was beautiful. She told him he should leave. This was it the end of my fantasy. Kyle grabbed his things and moved off camera into the dining room.
Tiffany looked completely bewildered but only hesitated a second before following after him calling his name. I switched to the other camera fast forwarding to where Kyle enter the dining room. He froze as Tiffany called his name. Turning to face her she walked up to him.
She took his things and let them drop to the floor. She went up on her toes and kissed him deeply. I fucking saw rockets. My heart was zooming as I watched what I hoped was my dream come true.
Tyler reached for the hem of her shirt helping her get the wet thing off. Her nipples were fully erect a combination of the water and her arousal. Kyle leaned down to suck and lick each one. Her head went back as she moaned with pleasure.
She lifted his head and kissed him again passionately as she wrestled to get his wet shirt off. After tossing it aside she rubbed her hands over his ripped chest and abs then licked and bit his nipples as she worked his belt lose.
I had to release my now hard cock and could only stroke it slowly as I was already on the verge of cumming.
His pants went to the floor and she followed them down kneeling in front of him. I had to admit a tinge if jealousy went through me for just a moment. We were about the same thickness but he had to be at least ten inches long. He was definitely a couple inches longer than me.
My jealousy faded as she feverishly stroked his ass as she sucked him or licked his balls. Their eyes remained locked together as she looked up at him while on her knees.
Kyle pulled her up to her feet. Her spun her around to face our table. He pulled her pants down and she eagerly stepped out of them. He pushed her forward so her hands rested in the table while pulling her lower body back.
He went to his knees and planted his face in her ass . Tiffany let out a gasp and a long moan. I had to admit his saviness at how to pleasure a woman was impressive at such a young age.
She went up on her toes and her hand went back to his head as she hissed telling him she loved having her pussy and ass licked.
The next thing she said forced me to squeeze my cock to keep from shooting my load. She told him to fuck her!
Kyle stood up and started to work his now rock hard upturned cock with a large head into her willing pussy. He was having a little trouble. Her hand shot down as she guided him inside of her.
She let out a very loud moan as he sank all the way in. He gave her just a moment before he started to fuck her. It was amazing watching them as her heavy tits swung as he fucked her and she pushed back towards him.
She moaned again when his hands moved to her tits as he continued to fuck her deep. Tiffany came and her legs buckled. Kyle kept her steady, she turned towards him and the kissed again. She sat up on the table pulling her knees up and legs wide.
Kyle licked her pussy a couple times causing her to gasp and arch her back. He stood and pushed his cock back in. This time he fucked her hard so she had to hold onto the table's edge.
Tiffany arched up again and her eyes rolled up in her head. She yelled his name as she came again. Kyle was panting wildly by this time. He asked her where she wanted him to cum. Without the slightest hesitation she yelled for him to cum inside of her.
That was it I tried to hold off but came all over myself. I sat there breathing heavily as he emptied his young balls into my wife’s pussy as she gripped his muscular arms and watched his cock sliding in and out. He fell forward on top of her as she locked her legs around his back.
He finally pulled out and helped her off the table, they kissed some more. She told him he was amazing but he needed to leave before I got home.
Kyle dressed and she walked him to the door still naked. She gave him a long goodbye kiss. After he left she sagged back against the door. I heard her say “Oh fuck what just happened.”
She went off to shower and I came home about an hour later. So what she was feeling was probably guilt about cheating and scared that she had just had sex with one of her students. I could see how that may may make her feel ill.
Over the next couple days she was about the same. She seem distracted and went to bed early claiming to be ill. I needed to find a way forward. Things didn’t look good when she said she wasn’t feeling well enough to tutor Kyle the next Sunday.
I went to Clay for an idea what to do next. He suggested we bring Kyle in on everything. At first I didn’t think it was a good idea. But Clay said Kyle was moping around as well. Clearly bummed that Tiffany had made excuses why he couldn’t go over again.
He thought Kyle needed to understand it could only be sex and nothing more. Explaining that if Kyle knew we had set this up under the pretense of helping her and I with my “condition”, he would know that we knew. We could then make him understand she wouldn’t see him anymore if she felt guilty about cheating. It sounded logical but I wasn’t sure it would help. But I didn’t have a better idea.
So we got Kyle out on the boat again and I brought up that I knew what happened between him and Tiffany. Of course he denied it at first until his father told him we both knew.
He was definitely afraid at first. I continued to let him believe I had a condition and that is why his dad and I put things into motion. But we wanted him to understand it was to be only sex. He was obviously confused at first. But after we explained to him it would have to be a one time thing if she thought there would be a risk of losing her marriage.
The power of good MILF pussy should never be under estimated. He did admit he was crushing on her bad. But he totally understood where we were coming from. But he was sure she wouldn’t have sex with him again. I smiled at him saying I think he was wrong. Thinking to myself no one should ever underestimate the power of a big young cock and a strong back.
Kyle asked his father if he thought his mother knew. Chad responded saying, “Boy we would both be at the bottom of this lake with cinder block slippers.”
Kyle asked me again if I was really ok with her having sex with someone else. I told him it wasn’t for everyone, but I was more than ok with it.
So I told him what we needed to do next. He was all ears. That next Thursday was the third such day of the month. Tiffany stayed late at the school to meet with parents by appointment.
She parked her SUV in the faculty parking lot on one side of the school in her own reserved slot. There were nearby places where one could conceal themselves with a perfect view of her car.
I parked on the opposite side of the school and made my way to a spot very close to her parked car but well hidden. She finally came out of the building she had just put her things in the back seat when Kyle pulled up on his motorcycle and stopped directly behind her car.
He asked her why she was avoiding him. She said she wasn’t but that she was just really busy. I could tell by her body language she was not sure what to do.
Kyle said he just wanted to talk to her. She initially told him she didn’t think it was a good idea. He promised her it was just to talk. He had received two separate scholarship offers and he wanted her advice. She tried to convince him to see her in the morning at school.
To his credit he didn’t give up. Tiffany looked around then told him to park his bike behind a nearby dumpster. He did as she asked then joined her in her car. There were no other cars nearby but she clearly looked around very nervous.
Kyle got into her car and pulled out some info on the two schools. They talked for a while I could make out most of it. She was telling him about the pros and cons of both schools. Both were a few states away and had different things to offer.
He finally settled on one. I think she expected him to get out of her car. He stuck to the script I had given him about understanding she had conflicted feelings about what happened. She told him it was wrong and her fault that it happened and he wasn’t to blame.
He said he understood, but he would be leaving in a few couple months to visit his mother's family back East. Then he was off to a football camp before heading to his new school early as well. He touched her cheek and said he just wanted to spend more time with her before he left.
Again she told him she couldn’t but she clearly was conflicted. He leaned in to kiss her and she pulled away. She told him she loved me very much and didn’t want to lose me. That was self assuring news. Kyle said he understood and just wanted what she would be willing to give him.
She looked at him without saying anything for a long moment. Then pulled his face to her and kissed him. In a flurry of flying clothes her dress came over her head as he moved to take his pants and shirt off.
They clumsily moved to the back of her large SUV. I could see her head moving up and down. After a short while the swapped an one of her legs hooked the front passenger head rest with the other over the back seat.
I could see his broad back and the back of his head. Tiffany was moaning steadily as he ate her pussy until she came with a shout. He sat up on the seat and she straddled him. There was enough light from a spotlight on the corner of the building that I could see he was feasting on her tits.
She raised up then lowered herself down, letting out a long slow moan. Moments later she was bouncing up and down on his young magical cock. At one point she had both hands braced against the roof of the car as she rode him to a screaming orgasm.
Kyle wasn’t finished even though she begged him to give her just a minute. He flipped her on her back and moved on top of her. Her protest died and was replaced with her yelling yes over and over again. She begged him not to stop fucking her. I heard him ask her if this was his pussy until he went off to school. She didn’t hesitate answering he could have her pussy anytime he wanted.
That was it she was hooked. Kyle fucked her furiously in the back seat. Her legs were flailing in the air as his ass went up and plunged back down. She was moaning screaming and grunting with every stroke. She came again and her feet were up in the air shaking like she was having a seizure. Kyle let out a yell as he came inside of her.
They laid there talking for a long time. I left them to it and rushed back home. She came in and immediately showered. She was clearly nervous yet very talkative.
I hoped Kyle had said everything I told her verbatim. She was clearly restless so I asked her if everything was ok. She asked me if I still had those fantasies about her having sex with other men. I stopped reading my book and asked her if that was a trap question.
She told me it wasn’t but just wanted to understand why I would be ok with something like that. I explained it to her honestly. That it didn’t mean I didn’t love her anymore. I just was very turned on by the idea of her being pleasured by someone. Addendums as planned that so many other people do it behind their partners back and that usually ends badly.
There was a momentary look of panic on her face. I realized technically she had cheated on me. But in all fairness she was entrapped be me. I was sure she had never done anything like this before.
I asked her if she would consider trying it at least once. I was ok with her next lie. She told me that my best friends son and her student Kyle was constantly flirting with her.
I asked her if she thought about having sex with him. She didn’t technically lie when she admitted she did. Even though she had already fucked him twice already.
She asked me if I wanted her to seduce him. I immediately told her I would love her to do it. She asked me again if I was sure. I placed her hand on my hard cock.
We fucked like crazy that night with me saying things like, "I have seen Kyle in the men’s locker room and he had a big cock." She came almost immediately on my own cock. Obviously she was thinking about feeling him deep inside her again soon.
Kyle showed up on the next Sunday. Headed of to golf as before. I had showed Tiffany the recently installed camera in our bedroom. I told her I put it there just that Saturday.
When I got home from golfing, she definitely had a just well fucked glow about her. Her hair was down and her lipstick still smudged. She was wearing a robe as she led me upstairs. The bed was a wreck and the room smelled of sex.
She asked me if I was ok. I kissed her, surprised at the taste of what surely was cum in her mouth. We took a quick shower together. I got my laptop and we watched the movie together.
They were both already naked when they entered our bedroom. I watched them kiss and get into a sixty nine with her on top. I loved watching her worship his young cock with her lips and mouth as her ass wiggled over his face.
They fucked in multiple positions with him cumming in her fucking her from behind. She deftly stroked my cock as we watched. The look of sheer lust on her face was amazing.
They cleaned up and talked for a while. She started sucking his cock again and soon he was really fucking her hard. He finally let her on top where she rode him until he told her he was going to cum. She climbed off his cock which was lathered up with her juices.
He let out a moan as sucked him like a mad woman. He warned her he was about to cum she only sucked and stroked him with more urgency. Until he yelled out “Ohhhhh fuck me!!!!!”
He came in buckets but only a little descaled her mouth. He went limp and she moved up his body and kissed him probably giving him his first taste of his own cum.
She sent him on his way, promising him to see him again soon. The video ended and I rolled on top of her. She eagerly pulled me inside of her already wet pussy. I didn’t last very long but that was ok.
We talked late into the night. She was convinced I wanted this and she admitted it was amazing for her as well.
Kyle was her regular fuck buddy until he left town. He would fuck her more when he was home during the holidays. I would always get to watch them later. A few times I had watched them in person which was even better than on video.
Hope you enjoyed this story....Part two soon.