Watching Mom the First Time Pt. 06

This is the 6th chapter about a Son and his Mom.

A little background:

Chapter One:

The Son spies his Mom masturbating on the couch while on family vacation. She later jerks him off and he shoots his load all over his Mom. He then eats his Mom to orgasm while she is in the kitchen preparing dessert and Dad is watching TV.

Chapter 2

Mom takes his virginity and has her way with him several times.

Chapter 3

Mom asks her sister to come over and help her with Terry and their scheme is to have their way with him. His Aunt catches him jerking off and blackmails Terry into all kinds of sexual acts while Mom makes plans to watch Terry take his Aunt's ass while Mom is hidden in the closet.

Chapter 4

Mom comes out of the closet.

Chapter 5

Mom and Terry spend their first night alone.

Chapter 6

Son and Mom Try Anal

Terry Spies Mrs. Martin Sunbathing

*****

The next morning I woke feeling a slight pressure on my dick. I reach down to see what is making my dick turn so hard. I feel hair covering my dick as I try to focus. Mom is giving me one hell of a blow job and started while I was asleep. I groan as she applies more force with her hand jerking my dick slowly.

"Good morning sleepy head, I thought this might wake you up," mom replied as she took in six inches.

"Mom, this is the best way I have ever woken up for sure."

Mom increased her sucking pressure as she fingered her cunt. I look down to see two of her fingers buried in her cunt.

"Sorry I started without you honey," moaned mom.

I reached over to replace her hand. I took in two of her fingers and licked off the juices. I inserted two of my fingers all the way in and bent them trying to reach her cervix. A thick, creamy feeling paste covered her cervix as I massaged all around the area. She was hot as hell down there. I could not wait until I had my hard dick in her pussy.

I was hard as steel as my mom straddled me and plunged all the way down, taking all nine inches at one time. I looked to see her pussy hair mesh with mine and knew I was as deep I could go in this position. I reached up and grabbed both tits pushing her back some so that I could drive my dick at a better angle.

Mom spread her legs further apart and arched her back as she bottomed out on my cock. I pinched both nipples and thrust up as hard as I could. The head of my dick bounced off of her cervix.

"OOOHHH MMMYYY GOOODDD! That feels great do not move that dick for any reason," cried mom.

Mom then eased up slightly and I could feel the head of my dick bump her cervix once again. Then mom lowered all the way down again causing the head of my dick to brush past her cervix. Time and time again, she repeated these moves.

"Honey, I am going to cum soon can you cum with me?" Asked mom.

"Mom, I really do not want to cum right now so go ahead and release for I can wait."

"Get ready Terry, I am going to cum all over you're hard dick!"

Mom grabbed the headboard to hold on as she came. Powerful spasms caused her to roll back her head and scream, "Cumming so hard now this is too good to be true!"

Mom came for about a good twenty seconds before she could talk. She collapsed and laid her head next to mine as her breathing slowed down. I placed my fingers near her ass and slowly inched towards her opening. Mom gasped as my middle finger eased over the opening of her ass.

So far so good since she did not say or do anything to stop the advance of my finger. I applied some pressure and then swirled my finger all around the opening of her ass. A slight groan escaped mom as my finger finally entered her ass. I found the nape of her neck and started to gently lick and suck as my finger went a little deeper. I now had my finger in one knuckle deep.

I could feel the intense heat as my finger gently massaged the inside of her ass.

"Honey, that feels way better than I thought it would ever feel."

I push mom up some to let my dick pop out and come to rest against her ass. The head of my dick is an inch higher than her ass. I can clearly see it sticking straight up hoping to find a home.

Mom rocks back with her pussy to rub up and down my shaft. I moaned slowly as she coats my dick with juices. I apply more pressure with my middle finger and the second knuckle slides in her ass. It is so tight that I think there is no way I will ever get my big dick in this little hole.

"Honey, I want to make you happy, but I tried anal sex one time but no luck. It hurt too much," replied mom.

"Mom, I promise to go as slow as you wish and will stop when you say so."

"Ok, let's try it, but remember you have to go really slow and go get the baby oil to help out some."

I practically ran to get the oil and mom had moved two pillows underneath her ass while I was gone. I climbed between her legs and poured some oil right on her pussy lips so see it drip down to her ass. I spread the oil all around the opening of her ass. I inserted one finger and massaged oil deeper.

"Please come up here and let me put some oil on that hard dick of yours."

I move up so that my dick was resting across her tits as she poured oil all over my dick, shaft, and balls. Pre-cum leaked out and landed on her tits dripping to the covers like she was waterproof. I moved back down and got in position so that my dick was in line with her ass. Mom placed her legs on my shoulders and this caused my cock to touch the entrance of her ass.

"Ok, try to get the head in but go slow and do not push at all. I will do the pushing."

I looked down to see the head of my cock push on the opening. Mom pushed towards my dick and this pressure made the head of my dick slide in just half way.

"Ooohhhh that is really big honey go slow," moaned mom as she gasped.

"Almost got the head in mom are you doing ok?"

"Yes honey, so far not much pain so try to get the whole head in next."

Mom pushed again and the head popped in and causing mom to hold her breath.

"Don't you dare move! Let me get used to this before we go any further."

I looked down to see the head of my cock buried in my mom's ass. I felt like I was going to cum right then, but knew better times were coming my way if I could just hold out longer.

I took my thumb and ran it across her clit, causing mom to moan and relax somewhat.

Her pussy lips were spread completely out showing great details about the insides of a women's pussy.

I wanted so badly to reach down and taste her juices, but knew that might cause my dick to slip out.

Heaven forbid that should happen. Instead, I inserted two fingers deep into her cunt as I found the oil and poured some more on my shaft.

"OH! BABY I AM GOING TO CUM NOW!!" Screamed mom as my thumb massaged her clit and my fingers plunged deeper into her cunt.

White thicker cream leaked from her cunt as she came all over my fingers. I then tried to push a little of my cock deeper into her ass. One inch went in deeper and mom used her hands to stop my advance.

"Oh God Honey, you are going to tear me apart with your huge cock. The feelings are fantastic at the same time," moaned mom as she pushed slightly, allowing my dick to go one more inch.

I now had about five inches buried in her ass, but yet only had taken four or five strokes.

"Mom I am now going to pull out some and then push back in if that is ok?"

"Yes darling, let's try that but remember to go slow."

I pulled out a good two inches and it felt like a vacuum cleaner was trying to keep me in her ass. The sensation was unreal. I did notice a very small drop of blood on my shaft as I pulled out my cock.

I eased forward and was able to get in about five and a half inches this time. The sensation and pressure being applied to my cock were out of this world. My mom was very beautiful as she lay there with my dick up her ass and her tits swaying after each slow stroke.

"God honey that is feeling better with each stroke," keep going replied mom.

I spread her legs further apart and applied more oil to my shaft. Mom reached down to feel my shaft and said "Damn you still have several inches more to go."

I took her hand and placed it on her pussy lips and held it there.

"Mom I want you to masturbate for me. You are so hot looking right now!" I moaned as I pushed one more inch deeper in her ass.

Mom plunged two fingers in her pussy and I rubbed her clit with my thumb. I pulled out three inches and pushed my hard dick back in with less force this time.

Mom was starting to loosen up some. I decided to try to develop a rhythm with my strokes to see how mom would respond. I stroked five good long strokes and Mom started to cum once again.

"OOOHHH SSSHHHIIIITTTTT I might pass out," cried mom as she came.

More thick white cream leaked from her pussy. I looked down and my shaft was covered with white cream and small amounts of blood. I knew I could not last long enough to get all nine inches in her ass. I had to have some release soon and noticed mom trying to grab my ass.

"I cannot last much longer what are you trying to do mom?"

"I want all nine inches in my ass as you cum. It does not hurt much at all now."

"Are you sure?"

"Yes honey please give me all of that hard cock deep in my ass. I am your slave from now on. This is the best sensations and I only wish I had my vibrator to shove deep into my pussy as you take my ass," moaned mom.

I pulled back out a good two inches and said, "Get ready mom here goes the other two inches," as I pushed until my balls slapped her ass and bottomed out.

The orgasm hits me like a ton of bricks and I was surprised I could not control it. Cum poured out of my dick splashing her insides with the force of a broken damn releasing spent up cum.

"I am cumming AGAIN HONEY! I can feel cum spurting deep into my ass please do not stop ever!" cried mom.

I reached down and inserted four fingers deep into her cunt as she rocked from her orgasm. Thick white cream coated my fingers as I plunged them in and out of her cunt lips.

My dick kept firing hot spurts of cum deep into her ass as she shook underneath me.

Mom passed out and went limp as I fired the last spurts of cum. I pulled out and a popping noise resulted when cum, blood, and pussy juices poured out of her ass.

Mom laid still while I caught my breath. I looked down at her ass and a small ring around her ass protruded outward contracting in rhythm with each breath my mom took. A small amount of blood eased from the ring as it retreated in size and disappeared back into her ass.

Mom laid there for another three minutes before waking up looking very dazed, but content.

"Honey, sorry I must have passed out. I remember when you stuck your fingers in my pussy and I could not take it anymore. That was the best orgasm of my life," moaned mom as she caressed my dick.

I kissed mom on the cheek and knew I wanted this to stay like this forever. Mom drifted off to sleep and her hand let go of my cock.

I rolled off the bed and headed to my bathroom.

I came out of the bathroom from my shower and walked down the hall towards my room. I hear Aunt Jean and mom talking in Jean's room. I ease closer to be able to hear what they are talking about.

"Cindy how was the first night alone with Terry?" asked Jean.

"Jean he wore me out and he also tied me up with silk ties," replied mom.

"He tied you to the bed???" asked Jean in disbelief.

"I was tied spread eagle with not a stitch of clothing on. He even sucked on my toes to start off the torture routine. He slowly licked almost every part of my body before he plunged his tongue deep into my pussy. I felt on fire as he ate me out to two powerful orgasms.

"Ummmm, I am starting to feel that tingly feeling between my legs," replied Jean.

"Once he had me begging to be fucked he only untied my two legs. He then placed them over my head and buried all nine inches deep into my pussy. He gave it to me hard and fast. I looked down to see his thick cock slamming my pussy and I could feel juices running down the crack of my ass after each stroke," replied Cindy.

"Mmmmm, how many times did you cum?" moaned Jean.

"I came so many I lost count. Every time he withdrew that huge cock of his he would then slam that cock back until he hit my cervix. I could feel his balls touch my ass with each stroke. The sensations of his balls bouncing off of my ass heighten the power of each orgasm."

"I am getting horny just listening to you right now," replied Jean.

"This morning he took my ass and I passed out from the intense feelings."

"I told you anal sex was the best once you go use to it."

"Well you had better get ready since Terry has asked his friend Billy to come over to spend the night. He will be here around lunch," replied mom.

"What does Billy look like?" asked Jean.

"He is the same height as Terry but with black hair. He has an athletic build, eighteen years old and he plays tennis on the high school team as a senior. Now that I am checking out guys Terry's age, I am pretty sure Billy has a huge dick. I did not notice this all the times Billy has swam in our pool until now. I can still see the image of his dick pinned against his shorts."

"I really could use a great fuck again before I leave tomorrow. Do you think I might get a chance at Billy?" replied Jean.

"If he is as big as I think he is then I might help you," replied mom laughing.

"Wow they both want Billy," I said to myself.

Thoughts ran through my mind as I walked to the bathroom on how I could use this to get my chance with Billy's mom. If Billy had his way with my Aunt he might agree to let me try to have my way with his mom. If not I could maybe work out a deal that included my mom if needed?

A couple of hours later I was headed to Billy's house to pick him up.

On the way out, I reminded mom that I was going to Billy's house to eat lunch and pick him up later in the day.

"Terry put on some suntan oil that has some protection since you are not wearing a shirt today," replied mom as I walked past them on the way to the lake.

Billy lived three coves over, but by road it was four miles. As I rounded the first point on the lake I looked towards Mrs. Martin's house to see her standing on her pool deck waving at me. I turn the boat towards her direction and waved back at her.

As I pulled the boat up to her dock, she motioned for me to come up the pool area. Her house had to be over 5000 square feet with the pool joining the house to make a picture perfect postcard of a dream home on the lake. Her Ex was in sales and from the looks of this place he could sell ice to Eskimos.

I walk up to her and notice she is in a two piece bright white suit that shows off her huge tits. She has tan lines that are well defined since she obviously lays out in the sun a lot. Her blond hair is tied up into a bun with two Chinese chop sticks holding everything together.

A pair of sunglasses covers most of her face since they are over-sized and have gold trim down each side of the frames.

I glance down to view her pussy area and her pussy lips form a small camel toe, indicating she has little if any hair around the lips. I am hoping she is completely bald down there.

She is holding a cocktail of some kind and takes a sip as I say, "Hello Mrs. Martin, how are you doing?"

"I am doing fine Terry; I waved you over to talk about the work that needs to be done around here tomorrow. I hope you do not mind," replied Mrs. Martin in a slurred voice.

"Mrs. Martin no problem at all," I replied.

"Please call me Kim since you are starting college this fall and I do not want to feel like an old divorcee."

"Ok, Kim what did you have in mind," I asked as I looked directly at her huge tits.

I walked towards her and she grabs my hand for me to follow her around to the side of the house. As we walked down the steps I notice her ass fills out her suit very nicely. Matter of fact, her ass is tighter looking than my Mom's ass.

She must work out to keep her ass that tight. She stops abruptly at the bottom step and I run right into her ass with my semi-hard dick.

"Sorry about that Kim," I explained as she turns around looking directly at my dick which is starting to come to life.

The Tommy Hilfiger swim suit I am wearing has a mesh lining to hold my cock somewhat in place. She looks up at me and smiles. We continue until we get to the side of the house.

She is pointing out the bushes that need trimming and I really am not paying much attention since her tits are almost falling out of her suit each time she bends over to show me how low to cut the bushes back. My dick is now at full mast and I tried to tuck it to the side.

"Follow me to the pool area since I need the bottom of the pool cleaned," replied Kim as she walked back up the stairs.

She once again stops abruptly at the last step and the length of my cock presses across her ass as I ran into her. She leaned back into me like she was going to fall and I quickly placed my arms around her at the waist to stop her fall.

She moans as her ass rubs against my cock and lingers a few seconds before she turns to say, "Thank you this hot sun is getting to me.

Do you see all the black spots on the bottom of the pool?"

We are standing at the shallow end and I lean over to take a look. Kim walks down the steps into the pool as I remained on the deck. She is waist deep in the pool and uses her toes to point to the black spots.

The water covers her bottom suit and makes it almost transparent instantly. I can clearly see her pussy lips as she moves her legs from side to side. She is totally bald down there and it looks like two smooth snow peaks coming together forming a valley.

Her face is eye level with my cock as she moves towards the side of the pool where I am standing.

She is pointing out the spots near the edge and dips down into the water up to her neck.

When she comes back up her top is now almost as transparent, showing every detail possible about her breasts. Her nipples have a large areola about the size of a half dollar with the nipple being about a quarter inch. She asked me to move closer to the edge so I can see the spots near the edge.

I move to the edge and her head is now eye level with my huge hard-on. I peer into the pool and see her cleavage expand each time she takes a breath. I really want to grab those two mounds of flesh and suck on them as she looks up at me.

"Terry, move closer to see all the ones near the edge," replied Kim.

I am now standing with my cock almost touching the back of her head as she points out several spots that need to be cleaned. My cock is now hard as steel and pointing straight out. I feel weak in my knees as she turns back to me and her cheek bumps into my dick.

"Oh my! Did I cause that?"

"Yes ma'am sorry about it."

"Don't be sorry for something so big Terry. Do you know that you have a special gift that many guys would love to have? Here sit on the edge of the pool before you fall in," replied Kim as she reached for me hand.

"What if somebody sees us," I asked.

"During the week, nobody really comes by my house in a boat to see us," replied Kim.

I sat down and Kim moved in between my legs. Her breasts bumped into my legs as she placed her hands on my knees. She pushed my legs further apart until she was between my legs and her tits were resting on my thighs.

"Can I tough that hard dick of yours?"

I moan a soft yes, as her fingers touch the insides of my thighs. She moves them slowly towards the tip of my cock. Her fingernail then traces the head of my dick down my shaft towards my balls. My dick lurches at her touch trying to escape from the tight confines of my suit.

"Wow! I wonder how big this dick really is," replied Kim.

She tugs at my suit as I lift up so she can pull my suit off. My dick springs back and hits my stomach with a smack. Her eyes widen in surprise as she takes a firm grip with her right hand. She stands my dick straight up and gives it one slow stroke. Pre-cum oozes out down her hand to the second finger.