"The Adventures of Alex VII: The Assistant"
Well everyone, it's been one week since My Dad and I had sex for the very first time. Since then, we have had a few more hot sessions. We also talked about some of the guys we've been with and we have two mutual friends, Coach Brady and Mr. Williams. In fact, that Sunday he went golfing, he had actually had gone to have sex with Mr. Williams. It was so hot doing something so forbidden. I loved being fucked by my Dad. It was great doing this without anyone else knowing.
The next week, my friend Dave was in an accident and broke his leg. He had been working as his dad's personal assistant at his office for the summer. His Dad, Michael Dean, needed a replacement. He was very good friends with my parents and they volunteered me for the job. I normally would have been pissed but Mr. Dean was a cool guy. Mr. Dean was a really cool guy and we had a lot of fun on trips with him. He was always really nice to us so I was excited to be working under him. He was 42 and in really great shape. He had dark brown eyes, salt-and-pepper hair, and was about 6'2". He had strong arms, a great chest with some light hair, and a six-pack. I always imagined what the rest of him looked like. I was always surprised why Mr. Dean never remarried after his wife left both him and Dave five years ago. He is a very attractive man, but a bit of a workaholic. Dave always complained about that.
I went pretty nervous on my first day. My Mom dropped me off at the train station at 7am. Mr. Dean was waiting for there so we could both take the train into New York City, where he worked. He was a financial analyst so his day started early; luckily it ended early at 4:30. Hanging out with Mr. Dean was like being with one of my friends, so I was completely comfortable around him. When we got to the office at 8am, I found out I had my own desk, phone, and computer. I got the requisite tour and Mr. Dean introduced me to his co-workers. He even told me I could just call him Mike, just like everyone else.
Things ran smoothly the rest of the month. I did all of my assigned tasks and took care of all of Mike's errands. One week in mid-August, Mike found out that he was being sent on a business trip to Boston. It seems that were was a big convention going on so he would need his assistant to accompany him for a whole weekend. I was so excited that I would be going away, especially since we were going to Boston. I had always wanted to go there. It was going to be just Mike and me so I was pretty happy about that. The day was fast approaching and I was really excited.
"So Alex, are you ready for our trip?" asked Mike two days before the trip.
"Yes I am Mike, I am pretty excited," I responded.
"That's great. Listen I wanted to let you know that because of the convention we were only able to book one room with one bed. You don't mind sharing? I could take the couch and you could take the bed."
"Well, Mike we could share the bed if you like. We have been in close quarters on camping trips before so I would be completely comfortable with it."
"Great Alex. I'm glad you feel that way," he said.
I was so excited after he told me that. The next night, I was so turned on at the thought of having him in bed right next to me the next time I go to sleep. I was sitting in the family room all alone downstairs. I was so horny. I figured I would jerk off. I was wearing only shorts so I slid them off. I grabbed my cock and got started. After a minute, the door opened. I quickly grabbed my shorts and covered up. Luckily, it was my Dad.
"Oh Dad it's you. I thought it was Mom," I said as uncovered my cock.
"Well Mom is fast asleep, she had a tough day at work. I wanted to see if there was anything you needed."
I noticed he was completely naked as he came around and stood right in front of me.
"I'm sure there's a lot you could give me Dad."
I got off the couch and kissed him. We had our arms around each other as we shared a very passionate kiss. Our arms were around each other. My Dad held me close to him. We stood there with our cocks on each other's cock and my hairy chest against his. Our hands caressed every part of each other's bodies, our arms, our backs, etc. We continued kissing as we began going down to the floor. We kneeled on the carpet as we continued to kiss. My Dad then lay me down on the rug. He sat with his legs open right on top of me. His cock rubbed against mine. He held my arms up over my head as he leaned down to kiss me. He slowly gyrated his hips so our cocks grinding together. It felt great.
He then kissed down my chest and stomach to my hard cock. He licked around the head and down the shaft.
"Ohhhh yes Dad, just like that...."
He went ahead and took me into his mouth. He sucked on my cock the way I loved it. Dad then stopped and got up. He squatted over my head so I could put his cock in my mouth, which I did.
"Ohhh yes son. Suck your daddy's cock...Ohhhhh!"
Dad leaned down on top of me and took my cock back into my mouth. There we were, My Dad and I were in a 69. I was so turned on. I sucked on my Dad's cock like there was no tomorrow. HE did the same to me. All that was audible were our muffled moans and sucking sounds. I had my Dad's ass right there so I went ahead and stuck a finger in, then another.
He jumped a little when I invaded his hole but he just gave in. We continued sucking each other. I knew I was getting close.
"MMMMMMMMMMMMMMM!" My Dad released his sperm in my mouth and let out a muffled moan. At the same time, I also released my load. We had managed to cum at the same time! It was so hot. My mouth was filled with Dad's cum and I filled his with mine. We continued sucking until all the cum was out. My Dad got off of me and lay down on his side next to me.
"You are so fucking hot son!"
"You are too Dad." He had some of my cum on his chin so I leaned in and licked it off.
"Things are going to get hotter Dad. Why don't you get on all fours?"
"Ok son."
Dad did just that and positioned himself on the rug on all fours. I kneeled behind him and placed my hand on the small of his back. I grabbed my cock, which was still hard and placed the tip at his hole. Then, I spread his cheeks a little and rammed my cock into my father's ass hole for the first time.
"UUUHHHHHHHHHHHH FUCK AL! OHHHHH SHIT!"
"Shhhh Dad, you don't want Mom to wake up."
"Uhhhh, sorry. You know how it is."
"I know." I started moving my hips as I held on to his. I loved feeling my cock deep within my dad's ass.
"Ohhh Daddy, I love how your ass feels on my dick."
"Fuck me son, yeahhh just like that."
My balls slapped against his as I fucked him faster and faster. Dad started jerking himself off while I rammed his ass. Oh, I cannot begin to explain how hot it was. I thrust in and out of his hot ass. I bet it looked great watching a son and his father fuck each other.
"Fill my ass with your cum son, I want it so bad! OHHHHH Yeah!"
"Almost there Dad! AHHHH."
I felt it coming. I knew it was only a matter of time.
"AAAAAAHHHHHHHHHH!"
My cum came bursting out of my cock and right into Dad's ass. Oh, man, it felt so incredible cumming in his ass. As my orgasm subsided, my Dad started to cum. He grabbed my shorts and blew his load right into them.
"OHHHHHHHHHHHHHHHHH Fuck Yeah!"
He moaned and moaned as he filled my shorts with his cum. I had softened up so I pulled out of his ass. We both collapsed on the carpet. I helped my Dad clean his cock with my shorts and we lay down to catch our breaths.
"Damn son, it felt amazing having you inside of me."
"You are so fucking hot Dad. I love sharing this it you."
"Me too Alex. We better start heading back to bed. I don't want your mom to come looking for us. Plus, I have to be up early tomorrow."
We both got up and went back to our rooms to sleep. I was beat.
************************************************************************ The next day, the day of the trip, my Dad and I left to Mike's house to pick him up and go to the train station.
"Damn, son. I'm really going to miss fucking you this weekend," he said while pulled out of the driveway.
"Me too Dad. But, I'm sure that Coach Brady or someone else will be there for you."
"That's true, but there is nothing like my own son!"
"I'm sorry Dad. I promise we'll make up for lost time when I get back."
"Ok son. I'll hold you to it!
We arrived at Mike's house and he was already waiting outside. It was hot so he was just wearing a t-shirt, shorts, and flip-flops. Man, he sure looked so hot. My Dad dropped Mike and I off at the train station at 4pm.
"Mike you better take good care of my son!"
"Don't worry Jaime, I will!"
"Bye Dad!" I said.
Our train left at 4:30pm. We had our own cabin and I really enjoyed the trip. We discussed some of the presentations that would be going on at the convention and then other general things. Occasionally, Mike would put his hand above my knee and would leave it there for a while. This was really turning me on. He would squeeze it and rub it a little. I wanted him so bad!
We arrived in Boston a few hours later. We left the station and grabbed a cab. Boston really was a beautiful city. It was different from New York City, but I loved it. After a short ride, we arrived at the hotel and checked into our room. The room itself was decent in size. The bed was a queen-sized one. It had a bureau and a TV. The bathroom was big enough with all the necessities. We were on the 11th floor so we had a balcony with a great view. I went out there to take a look and Mike joined me.
"It's beautiful, isn't it?" said Mike.
"It sure is. This is my first time here in Boston and it really is a beautiful city. It is so much more different than New York."
"I can't wait to show you the city, you will love it. It is a little late now though, do you want to order some room service and relax?" he said.
"Sure Mike. I would love that. I'll place the order."
"Great. Just get me a burger and fries Al, screw the diet for today." We both laughed.
I placed the order but they said it would take over an hour to get to our room because of how busy they were.
"I'm going to take a shower while they bring the food up," he said. He went into the bathroom and undressed in there. I was a little disappointed. I wanted to look hot when he came out. I took off my shirt and lay back in bed with my arms behind my head to watch TV. After about 20 minutes, he came out of the bathroom. I couldn't help but notice how hot his body looked. He was slightly older than my Dad, but just as hot. I was glad to see he was just in his white briefs. He eyed me for a bit then when about his routine. He lay in the bed next to me to watch TV. I wanted to him to just grab me and fuck my brains out. We just talked for a bit and he told me about how hard he was working and wished he had more time for Dave and himself. The conversation was actually getting pretty good. Unfortunately there was a knock on the door. It was room service.
The bellboy looked at us in a funny way. I guess since we had one bed and he just stood there in his underwear and I was shirtless. When he left, we ate our food and watched TV. Once we finished, we cleaned up and just fixed the room a bit. I noticed he took out a few more tighty-whities. I had an idea and I did not want to let this moment slip.
"You know Mike. There are other types of underwear besides tighty-whities," I said.
He laughed and looked down at himself. "I know Alex. I just never have the time to buy anything new. What do you wear?
I seized the opportunity to strip down. I wanted to mess around with him so I just pulled down my shorts. He must of thought I would just tell him, not show him. He just stood there and watched me as I undressed. I felt like a stripper and so fucking sexy. I could feel his eyes on me as I slid down my shorts, exposing my black jock strap.
"Holy shit Al, you have really grown up into such a good looking, handsome man," he said.
I looked up at him and smiled. My plan was working. "Thanks. I would have to say that you look great too, man. You really keep in shape."
"Thanks Alex. I really do try," he said and smiled. "You wear that regularly like underwear? I didn't know you could."
"Sure Mike. I use a lot of different types of underwear. They feel great and have great support. In fact, I know Dave wears them too."
"That's cool. I really didn't know he did too. You younger guys are so much ahead of me."
"Come on Mike, you aren't old at all. I have an extra pair in my bag. If you want, I don't mind if you use one so you could feel how it is. The straps feel great around your legs," I said. When I said that, I sort of turned round so he could see my ass. I ran my fingers under the straps and snapped them back. It turned me on so much knowing he was watching me. I then went through my bag and pulled out another black jock strap.
"Here Mike, try these on to see if they fit you," I said as I threw them over to him.
Hey caught them and seemed a little hesitant about getting naked there.
"Come on Mike. We're both adults plus it's just us guys here. I didn't think you were the shy type. Go ahead. I don't mind at all," I said.
He laughed. "Yeah you're right Al. Don't mind me. I just had a moment there."
He started pulling down his underwear. Out flopped his six-inch cock. He had a thick bush, which I loved how it looked on him. I wanted him inside of me so bad.
He then started to put the jock on. I noticed he was having some trouble with the straps. I seized another opportunity to get even closer.
"Looks like you are having some trouble, let me help."
I went up to him and pushed his hands away. I proceeded to pull up the jock for him. My hands were flat against his legs as I lifted it up. I took a big risk and grabbed his cock and adjusted it for him.
"Uummm, Al. I don't think you should...."
I cut him off quickly. "Don't worry about Mike. Just let me take care of you."
He just stood there and breathed in deeply. I softly adjusted the straps while softly stroking his legs. I just closed my eyes and breathed in his smell. My plan had worked. I had successfully turned him on. I noticed his cock was hard sticking out from the jock. Mine had started to grow as well. I straightened up and looked right into his green eyes. Our faces were mere inches from each other.
"You really are hot Mike," I said. "You look amazing in the jock."
"Umm, thanks Al. You are great too."
"Thanks." I inched closer to him and placed my hands on his hips.
"Al, I don't think this is really appropriate. I mean..."
"Shhhhhh. It's ok. I don't mind at all and from what I can tell you don't either." I slid my hand in the jock and stroked his hard cock. He closed his eyes and breathed in deeply. I leaned in and gave him a soft kiss. He had such soft lips. I then pulled him in and kissed him more passionately. Our tongues met and our hands all over our bodies. He then pulled away.
"I'm sorry Alex. I just can't. You are my son's best friend, my best friend's son and my employee. We can't do this. I'm a married man."
"Oh Mike. Haven't you ever heard that what they don't know wouldn't hurt them? Come on, I know you want me and you know I want you." After I said that, I took off my jock and stood there completely nude. I wasn't going to let this opportunity go to waste. I went over to the bed and lay down. I leaned on my elbow and looked at him. I grabbed my cock and started to jerk it a little.
"Come on Mr. Dean. Fuck me now."
I had to admit, it got me off calling him "Mr. Dean" right now. He looked at me and swallowed. He then slowly walked over to the bed. I grabbed his arm and pulled him on the bed. I threw myself on top of him and our hard cocks rubbed against one another. I leaned in and kissed him. This kiss was so fierce and intense. He had so much pent up passion to let go.
I kissed his neck and shoulders. I made my way down his hairy chest, licking and kissing it. I loved how he felt against my lips. I continued down his firm, hairy stomach to his jock. I slowly removed it and his rock hard, 8 inch cock came out. He had a beautiful head and was very thick. It had thick veins. I wanted it so bad. I loved that fresh clean smell he had. I grabbed his cock and started jerking him off while I sucked on his balls.
"No, ahh, Alex, I don't think...ohhhhhh baby. Ohhhh yeah."
I grabbed his cock and sucked on the head, swirling my tongue over his head. His precum tasted so sweet. I loved hearing his moans as I took it all the way in my mouth until his thick bush tickled my nose.
"OHHHHHHHHHHH ALEX, don't stop."
I continued sucking on his cock while my hands fondled his hairy balls. I could not believe I was sucking the cock of my best friend's Dad.
"Ohhh yeah, yeah Al. Oh baby, suck it just like that. Ohh fuck," he said while panting heavily.
I went as fast as I could and I knew he was getting close...
"AHHHHHHHHHHHHH FUCK!!!!! OHHHHHHHHHHHHHH BABY!!!!"
He screamed as his orgasm began and he released his come into my mouth. Ropes and ropes of semen poured into my mouth. I savored the salty taste and swallowed every last drop. I made sure that not one bit of it went to waste.
"Ohhhh Alex, you are so fucking hot son."
I went back up to his face and kissed him. I made sure I saved some cum and we shared it together. He grabbed me and hugged very tightly. He then rolled me over and he pinned my arms back. I moaned as his hairy body rubbed up against mine and he kissed my neck and shoulders.
"Ohhhh Mr. Dean, just like that baby," I said.
He remained quiet and was kissing me all over. He went down to my nipples and sucked on them hard. I moaned in total ecstasy as I had successfully seduced this hot man all on my own. He continued kissing down my chest and followed the slight treasure trail I had to my hard cock. His strong hands were holding me down firmly in place. He grabbed my cock and stuck it all the way down his throat. He took in every last inch of me.
"OOOOOOHHHHHHH, Mr. Dean," I moaned.
He slid his mouth over and over my cock. I could see the combination of my precum and his saliva dripping from his lips and down my shaft. I was moaning and squirming underneath as this hot DILF sucked me off.
"Yes Mr. Dean, faster, faster, ohh yeah!" I screamed.
Mike moved on faster and faster. I was panting heavily from the heavy number he was doing on my cock. His fingers had found their way to my hole and he slid two of them in there. I was practically screaming in pleasure at this point. He slid in a third and I could not take it anymore.
"AAAHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH!"
I released my load of cum into Mike's mouth. I thought the orgasm would never end. The tremors kept on going and going. Ropes of cum shot deep into his throat. Eventually it subsided and Mike cleaned off my cock and drank up every last drop of cum. I just laid back in the bed and let him do as he pleased.
"OHHHH Mr. Dean, you have an amazing mouth."
"Shhhhhhh, baby. Just stay there, stay right where you are," he whispered gently.
He took my legs and lifted them all the way up, leaving my ass exposed to him. He lay down with his face right at my ass. He spread my cheeks, exposing my hole to him. Using his tongue, he started licking up and down my ass crack.
"OHHHHHHHH Mr. Dean, that feels sooo good," I said.
His tongue then circled around the rim of my hole. This felt amazing. No one else had done this to me before. He then took his tongue and stuck it all the way in my hole.
"OHHHHHHHH Mr. Dean! Ohhh my god!"
He was eating out my ass. His tongue was licking all over and raping my hole. I had never felt anything like that before. It was amazing. The sensation was unbelievable. My hands were clenching the bed sheets as his tongue continued invading my hole. My cock was rock hard again and precum dripped off from the slit. His face was buried in my ass. After a while, he stopped and kneeled in between my legs. He grabbed them and threw them over my shoulder. The head of his cock was right at my opening.
"Fuck me Mr. Dean! Fuck me please!" I said.
In one swift movement, Mr. Dean rammed his hard shaft right into my ass.
"AHHHHHHHHHHHH! OHHH SHIT! AHHHHHH!"
It hurt a bit but it quickly stopped. His cock filled my empty hole and I felt his hairy balls on me. He started fucking me hard, like a madman. I felt his big balls slapping my ass as he rammed me with his thick member. Our bodies were hot and sweaty. His sweat dripped off of him and onto me because of the speed at which he was fucking me.
"You have such a fucking tight ass boy. You feel so warm inside. Ohh baby, you are hot!" he said.
"Fuck me Mr. Dean, give it to me hard!" I yelled, practically out of breath. "Oh yes, oh yes, just like that."
The bed was shaking like crazy. The headboard was banging against the wall. We were both screaming so loud. I was certain everyone could hear.
Mike continued to fuck me. I could feel a second orgasm building. I knew from his moans that he would cum again soon. Then he let out a deep moan.
"OOOOOOOOOOOOOOOOOOOHHHHHHHHHHHHHHHH FUCK!! OHHHHHHHHHHHHHH SHIT YEAH! AHHHHHHHHHHHHHHHHH!"
Just hearing him triggered my own orgasm. I shot my load all over my chest and stomach. This was so fucking hot. He continued pumping me as he let out his full load within my ass. He stroked my cock and milked out every last drop. Once his cock had softened, he pulled it out of my ass. He leaned down and kissed me. I really loved kissing him.
"Thank you so much Mike. That was amazing."
"No thank you Alex. I'm just hoping that we didn't cross any line or that I took advantage of you. You are only 18, I'm 42."
"We did not cross any line Mike. We are both consenting adults. I wanted it as much as you did."
"Yeah, I know. You are right Al." He leaned down and kissed me again. He then got off the bed and grabbed a towel. He cleaned off the cum from my chest and stomach. He also cleaned my cock and some of his cum that dripped out of my ass. He touched me so gently and caressed me with his strong hands. He kissed me again.
He lay on the bed beside me and held out his arm. I lay my head on his chest and my hand around his stomach. I just loved feeling his hairy body. He put his arm around me and we just fell asleep. ************************************************************************
I woke up late at night. The clock read 2:35am. I sat up in bed and looked over at Mike. He was fast asleep. I looked outside and it was a beautiful night. I decided to get some air so I got up from the bed and made my way to the balcony. I grabbed a robe from the sofa and threw it on. I figured no one would see me since it was so late so I didn't bother tying the front. Besides, my cock needed some air after that work out.
I stepped outside and it was very nice and warm with a slight breeze. The wind felt so good against my skin and my cock. I leaned on my elbows on the railing. I thought about all that I had been through the past 8 months and all the people in my life that have changed me, sexually: Coach Brady, Dee, Jason, Samantha, Mr. Williams, Brad, Dad, and now Mike. I could not believe the luck I had and all the experiences I have gone through in less than a year. I was so happy with the way things were going and could not wait until I got to college in the fall. I was so deep in thought I didn't hear Mike come out onto the balcony. He stood right behind me with his hands on my hips. He also had a robe on and left it untied too.
"Hey buddy. What are you doing here all by yourself?"
"Oh nothing. I was just thinking about all of the great things I have been through this past year. You wouldn't believe it if I told you," I said. I stood up and leaned against him. I tilted my head back and placed it on his shoulder.
"Well judging from what happened earlier, I bet they were incredible," he said as he kissed my neck. I just breathed in deeply as his kissed my neck and caressed my chest with his fingers. He pulled the robe off my shoulder and kissed me there. I could feel his cock grow and press into me. He grabbed my cock and started to jerk it. I looked up at him and kissed him on the lips. He lifted my robe up and leaned me over. I held onto the railing so that I was in the same position as when he found me. Again, he entered me with one quick thrust and his cock was inside my hole once again.
He started fucking me hard and fast as I jerked myself off. It was so awesome getting fucked on the balcony, knowing that anyone could see or hear us. We both kept quiet, the soft breeze blowing on our bodies as he fucked me with such passion and ferocity. I loved it when he took me and fucked me hard and fast as he lit my ass on fire. All you could hear were my pants and moans, his groans, and his balls slapping against my ass. I moaned as he fucked me faster.
"You like that don't you Al."
"Ohh yeah Mr. Dean just like that."
His pubic hair tickled me each time he thrusted. He quickened his pace and I felt as he filled me with his semen for the second time that night. He let out a soft moan from the orgasm he was having. I jerked off faster and released my load. I spilled it all and formed a puddle on the floor. I cried out a little but I don't think any one heard. He pulled out of me and fell back on to one of the chairs as he tried to catch his breathe.
"Oh wow, you are so fucking hot Alex."
"So are you Mike. I love the way you feel inside of me and the way your body feels against mine. You really are an amazing fuck," I said.
"We better get back inside and try to catch some sleep. We have a busy day tomorrow. Let's save some cum for tomorrow," he said.
"Yeah you're right. I am so fucking tired. I think my ass has had enough, at least until tomorrow."
We both laughed and walked back into our room. It would be a very interesting weekend....
Written by Jay www.confessionsofabi-guy.blogspot.com