"Hey mom! Look!" I said as I barreled off the end of the board.
When I surfaced I heard mom telling me to be careful. My plan had worked though because her attention wasn't on Steven any more, a fact that didn't go unnoticed by my friend. He was glaring at me but I just smiled at continued to swim. For the next hour or so any time that Steven made any advances towards my mom I would do something to get her attention. I even faked cramps once. Eventually my game plan was foiled though. Steven got out of the hot tub to get my mom another wine cooler. On his way to the house he leaned over the side of the pool.
"Cut the shit man. You're breaking the rules. Tell her you're going home or the bet's off." he said.
Now I knew I was probably bending the rules just a bit so I wasn't mad for him wanting me to leave. Besides, there was no way I was going to let him pull out of the bet after all this time. I told mom I was feeling tired and was gonna go home. She said she wouldn't be much longer so I grabbed my towel and pretended to leave. About five minutes after I left I walked back into Steven's house and took up a spying position at the window above the kitchen sink. With the blinds drawn almost shut I could see them but they couldn't see me.
Steven and mom sat in the hot tub for a while laughing and splashing water at each other. As they were fooling around Steven made his move and slid right up beside my mom. She didn't seem to mind even when Steven put his arm around her shoulder. They talked for a few more minutes then I saw Steven take his arm from around my mom's neck and it disappeared from view as it sank under the water. I couldn't hear what they were saying but mom appeared to be in mid sentence when her eyes widened. Steven just looked straight forward. Slowly mom started talking again and everything appeared to go back to normal. Mom laid her head back against the back of the hot tub and slowly her eyes closed. I waited anxiously as I watched for any sign that Steven was making any headway. They both sat in the hot tub motionless for a while and I was just beginning to relax when I looked back to my mom's face. Neither she nor Steven had moved an inch but her mouth was now halfway open. With her head leaned back and her eyes closed it looked like...well. I'm not going to say what it looked like. I started to panic not knowing if Steven was doing something to her under the water.
"Calm down, it could just be the water jets making her do that." I told myself.
I continued to watch for another ten minutes or so hoping that I wasn't seeing my chances of winning the bet unravel in front of me. I kept staring at mom's face trying to see if anything changed. Just a few seconds later I saw mom stand up in the hot tub. I prayed that Steven had gone too far and that she would tell him off or something but nothing happened. Mom got out of the hot tub and walked back to her lawn chair were she laid down on her stomach.
Steven got out of the hot tub and brought another lawn chair over right beside moms. I was just glad that now I could see what was going on without the water there to hide Steven's actions. Mom laid there for a few minutes with Steven sitting beside her talking. Everything calmed down for a bit then Steven picked up a bottle of sun tan lotion and appeared to ask if he could rub some on my mom's back. Mom raised her head and nodded her approval. Steven rubbed some lotion on her shoulders and upper back. He was quite brave as he applied lotion to mom's lower back and sides. He came very close quite a few times to the exposed sides of mom's breasts. I could see them pretty well even from the window so I knew Steven was getting an eyeful. Steven kept rubbing mom's back and shoulders for so long that I knew damn well that the lotion was thoroughly applied. He was more massaging her than rubbing the lotion in. As I looked on I saw Steven use one hand to quickly untie the back of mom's bikini top. He did it so fast and while one hand was still rubbing that I don't think mom realized what had happened until it was already done. Steven didn't give mom any chance to say anything either as he continued to massage her back. The sides of mom's breasts were fully exposed now and I was fuming as Steven stared at my mom's exposed flesh.
Steven continued to massage my mom's back slowly working his way down. Once he reached the small of her back he wrapped his hands around her waist and started to slide his hands up slowly. I knew that if he kept going his hands were going to touch the sides of mom's breasts. Mom's arms were raised with her head lying to the side resting on her forearms. I watched in slow motion as Steven's hands slowly glided up mom's side. My mouth opened as Steven's fingers glided across the sides of mom's naked tits.
"C'mon mom....don't let him..." I said quietly.
To my dismay mom didn't move a muscle, even when Steven's hands moved back down and once again his fingers slid over her breasts. He repeated those movements for a little while. I think he was testing the waters because he seemed to go lower every time. Slowly but surely his hands kept going lower until eventually his hands were sliding over mom's hips with his thumbs clearly gliding over her butt. He kept up his massage until his hands were sliding down mom's thighs. I wanted so much for mom to say something or do something to stop him.
"What the fuck mom?" I said.
Steven looked to be having the best time of his life. He was grinning broadly as his hands caressed my mom's skin in places I thought he would never even get close to. Steven took a second to put some more lotion on his hands before rubbing back up mom's thighs until he got to her ass. I guess he thought he was irresistible because he untied one side of mom's bikini bottoms. I was about to shit when I saw mom's hands quickly retie the knot. Steven stopped in his tracks as mom retied her top as well. I breathed a sigh of relief that the torture session was over.
Mom sat up in her chair and took a big drink of her wine cooler. She talked to Steven for a while. I thought she might tell him off but they both smiled the whole time. A few minutes later mom got up and got into the pool. She swam a bit before Steven got in as well. I watched as they swam and was beginning to think maybe I could go home. Steven splashed mom with a big wave of water which caused mom to return the favor. Before I knew it they were almost wrestling in the pool. Steven dove under water and mom turned in circles looking for him. She was laughing loud enough for me to hear her in the house. I also heard her scream when Steven came up underneath her and tossed her. They horse played like that for a little while until mom appeared to get tired. She swam to the side of the pool and rested her head and arms on the edge of the pool. Steven swam right up behind her and rested his head on her shoulder. His hands were under the water again so I didn't know what was going on. They stayed like that for a few minutes then mom got out of the pool and dried off. As she was drying her hair out Steven got out of the pool and I cursed out loud. Even from the window I could see that he was hard as a rock. He stood beside mom with the front of his trunks bulging out while he dried off as well. Mom didn't blatantly look but there was no way she wasn't aware of it. She wrapped her hair in the towel and put back on her shorts and t-shirt. Just when I was about to bolt I saw Steven walk up behind her and wrap his arms around her waist. I couldn't tell exactly how close he was but I hoped mom wasn't letting him touch her with his erection. Mom turned her head and kissed Steven on the cheek before heading towards the house. I ran like the wind back home and was upstairs before mom got to our front door. Later she came up and asked if I had fun. I pretended that I had and told her I was gonna hit the sack. She said she was going to do the same after a quick shower.
Just before I turned the light off in my room the phone rang and I saw that it was Stephen on the caller I.D.
"One more day and you owe me big man." I said immediately.
"That's all I'll need. Did you see earlier? I had your mom eating out of my hand." Steven said arrogantly.
"Whatever man. Hugs and massages aren't what we were betting on. You got a long way to go." I replied.
"It's cool man. Look, tomorrow night around seven, I need you to tell your mom that you're going to a party or something. I'll wait a while then go over and seal the deal." Steven said.
"Uh huh..." I said.
I wasn't sure about leaving them alone but I knew that I had to do what Steven said. It was his last chance and I knew I could just sneak back later and spy on them anyway.
"Cool, just remember that you better have proof or it's gonna be time to pay up sucka." I laughed.
"I got a new cell phone just for tomorrow..." Steven said before hanging up.
I laid in bed for a while thinking about what happened today. Steven had taken some liberties and gotten away with them but so what. He either had to have sex with my mom by tomorrow night or I was gonna be a thousand bucks richer.
The next day I woke up pretty early. I knew that today was the last day of the bet and I could almost smell the money that would soon be mine. I walked downstairs and told mom that later tonight I was going to a party. She told me to be careful and to not drink any alcohol. I reassured her I wouldn't before playing some video games for a few hours. About six, I got up off the couch and went to take a shower. After I got some clothes on I walked downstairs to tell mom I was going out for the evening.
"I'm gonna go ahead and go to the party. A couple guys from school I know got a band to play and everything." I lied.
"Alright, just be careful and don't come back too late, ok?" Mom said.
I got into mom's car and drove off down the road. I circled the block a few times then I parked down the street a bit before turning off the engine and the headlights. It didn't take long before I saw Stephen walking up the sidewalk towards the house. Stephen knocked on the front door and moments later I saw mom let him in. I snuck up to the house and peered in through the window. They weren't in the living room so I went around to the back of the house. The window right above the kitchen sink was open a few inches and as I got closer I could hear them talking.
"Why didn't you go to the party with Rich?" Mom asked.
"He was supposed to meet some girl there and I didn't want to be the third wheel. He would've done the same for me." Steven said.
Mom and Steven talked for a while longer before going into the living room. I made my way back around the front of the house. Without any open windows I couldn't hear anything that was said but I had a good view.
Steven sat down on the couch followed by mom. She'd apparently been having a little wine tonight because there was an empty glass on the coffee table. They both got comfortable and watched T.V. for a while. After about thirty minutes I saw Steven stand up and motion to the kitchen. Mom nodded and Steven grabbed her wine glass before walking out of the living room. While I waited on Steven to come back I looked at mom sitting on the couch. She was wearing a simple light blue dress. She must've expected to spend the night alone because her hair was down and she didn't appear to have any makeup on. My thoughts were interrupted by Steven coming back into the living room.
"Damn, you think that's enough?" I thought to myself as I saw mom's wine glass filled to the rim.
Mom didn't take her eyes off the T.V. as she brought the glass to her lips and took a big gulp. Things went on uneventfully for a long while after that. It was so boring that I was starting to nod off as I kneeled in the grass. A while later I glanced at mom's glass and realized that she'd drank the whole thing. A few seconds later I noticed that Steven had put his arm around my mom's shoulders. That must've been his favorite way of breaking the ice because it wasn't the first time I'd seen him do it. After nothing happened for a little while I sat down to give my legs a brief rest. I checked my watch and was relieved that it was almost eleven.
"Just a little while longer and I'll win this fucking thing." I thought.
After my legs felt less like jello I stood up again. The sight that greeted me was enough to cause some concern. Mom had her legs up on top of Steven's as she watched television. I watched intently as Steven brought his hand up and sat it on my mom's knee. I bit my lip nervously as mom remained unfazed by Steven's actions. Mom glanced over at Steven and I thought she might say something but she simply smiled. The next thing Steven did caused me to stop breathing for a moment. As I watched Steven slid his hand up under mom's dress. My heart started to accelerate. As she watched T.V. mom used one hand to take another drink of wine as the other pulled Steven's hand out from under her dress. Steven was undeterred though because soon his hand was back on mom's knee. He kept his hand there for a while before leaning over and lightly kissing mom on the shoulder. My mom just took another big sip of wine. Out of the corner of my eye I saw Steven's hand slip under mom's dress but not too far. It appeared that he was testing the waters again. Mom sat there unfazed for a bit, that was enough for Steven I suppose. Slowly is hand started to move upward.
"I know he's not gonna..." I said as Steven's hand slid even further under mom's dress.
Mom's mouth opened slightly and she leaned her head back against the couch. I couldn't tell exactly where Steven's hand was but I could guess. I couldn't quite believe that she was sitting there with Steven's hand god knows where under her dress. Steven leaned over and I thought he was going to whisper something else to her but he began to kiss my mom's neck lightly. His hand was moving a lot under mom's dress but from my vantage point I couldn't tell what was going on so I made my way to the window right behind the T.V. As I slowly peeked in my mouth fell open.
"Oh shit..." I thought.
From this spot I could see exactly what Steven's hand was doing. Mom's dress was pulled up pretty far and I could see his hand rubbing the front of her panties. I started to breathe really hard at this point. Mom was wearing some tiny white panties and Steven's hand was cupping her pussy. I looked up at her face just in time to see Steven kiss her deeply. Mom put her hands on Steven's chest as if to push him away but she made no real effort. Eventually mom's hand grabbed the back of his head and they made out like teenagers. I watched as Steven's hand pushed mom's panties to the side a bit and for the first time I saw her pussy. The tiny landing strip caught my eye and even I had to admit it was sexy.
"C'mon mom...don't do this..." I pleaded.
Steven rubbed up and down mom's slit until he finally inserted his middle finger into her depths. I watched her face contort as my best friend finger fucked my mom. My mom squirmed and wiggled on the couch as Steven kept up his assault. I don't know how long that went on but eventually she clinched her eyes shut and grabbed Steven's wrist with her hand. I couldn't believe what was happening as I watched my own mother cum on my friend's fingers.
"It's ok...he hasn't had sex with her....just fingered her." I said to myself.
After a few minutes mom let go of Steven's hand and he kissed her again. Their mouths were open wide so I knew there was definitely tongue involved. Steven stood up quickly and took his shirt off. Mom laid there with a blank look as Steven pulled his pants and underwear off in one long motion. I couldn't believe that I was looking at my best friend naked standing in front of my mother. I couldn't help but notice that Steven was pretty big. I measured myself one time and was happy with my seven inch cock but Steven looked to be even bigger. Mom just sort of sat there staring, she didn't look like she was sure what to do next. Steven took her hand and placed it on his cock. Mom slowly started to stroke up and down as Steven leaned his head back in pleasure. Mom had one hand on Steven's cock while the other was over her mouth. It was like she couldn't believe what she was doing either. After a while Steven put his hand on the back of my mom's head and pulled her towards his cock. My mom shook her head and braced her hands on Steven's hips. Maybe there was hope after all I thought. Steven was undeterred though. He brought mom's hand back to his cock. Mom was looking up at my best friend as she stroked his hard cock. Steven leaned down and kissed her again. They kissed for a long time with mom's hand sliding up and down Steven's cock all the while. After the kiss Steven stood up and again slowly pulled her head towards his cock. The kiss must've weakened her resolve because the time mom opened her mouth and sucked about three inches of Steven's hard cock into her mouth. Steven let out a moan I could hear through the closed window. Slowly but steadily Steven began rocking his hips as he held mom's head with both hands. Eventually he was face fucking my mother right in front of me. Mom's pink lips slid up and down Steven's glistening cock and before long she was taking almost the whole thing down her throat.
"Jesus Christ..." I said as mom gave Steven the best blow job he'd ever had.
Finally Steven pulled his cock from mom's mouth and pulled her to her feet. He kissed her briefly before turning her around. Steven got on his knees and unzipped mom's dress slowly. Afterwards mom pulled the dress down and I saw Steven take his cell phone out of his pants and put it on the coffee table. I knew that he was filming what was happening but there was nothing I could do about it. After putting his phone on the table Steven turned his attention back to my mom. He slowly pulled her panties down her long legs. He head was even with mom's ass as he grabbed her rear tightly. He squeezed mom's ass tightly before slapping her ass lightly. Steven remained on his knees as he guided mom and onto the couch. Mom was wide eyed as Steven spread her legs and brought his head down to her pussy. Her head shot back against the couch and she grabbed Steven's head with both hands. I watched the back of Steven's head for about twenty minutes as he ate my mom's pussy. He must've knew what he was doing because mom sure liked it. I could hear her moan from outside. Her eyes were closed most of the time and once in a while her tongue would trace her upper lip. Before long, as I watched wide eyed, mom's legs clamped tight around Steven's head and she came again. After convulsing for close to a minute, mom's legs eventually fell apart limply. Steven eventually got up and they kissed again for a long while. My friend then stood up and pulled mom to her feet. Then he sat back down on the couch with his cock pointing straight at the ceiling. I watched as my mom ran her fingers through her hair before straddling Steven. I could hear her moan loudly as she lowered herself down onto his cock. My mouth fell open as inch after inch of my friend's cock disappeared into my mom's pink pussy. Mom sat still for a moment before she started to ride Steven's cock. I watched intently as her wet pussy slid up and down Steven's hard cock. His hands were all over mom's tits but I couldn't see them with her back to me. That was soon remedied though as mom got up and turned around. She grabbed Steven's cock and guided it back into her pussy and she bounced up and down on his cock. Steven brought his hands around to mom's tits and squeezed them tightly.
"Oh shit..." I thought as I noticed that my own cock was rock hard. By this time I had lost all track of time.
Mom's head was leaned back as Steven fucked her hard. His hands left mom's tits as he grabbed her hips and began to thrust upward as hard as he could. Even with the window closed I could hear mom moaning. Steven fucked her hard and fast for another five minutes or so before he slammed her down on his cock as hard as he could. Mom was grabbing her tits with her head back as Steven came inside her pussy. I could see his balls convulsing as he emptied his cum into my mother. Mom ran her fingers over her tits as she sat on Steven's lap. She leaned back against him and kissed him again. As I watched, Steven's limp cock slipped from my mom's pussy followed by a large amount of cum. I fell backward into the grass breathing heavily as I processed what I'd just seen. I almost forgot about the bet when I looked at my watch.