Caning Freddy

Caning Freddy By Wolf

It all started when Freddy moved up from middle school to upper school.He was sent to a boarding school for the first time when he was 16- years old.That was the first time he was to be away from home.He was assigned a roommate named Charles.

He thought Charles was a nice enough guy.It was also his first time away from home.He was a little taller than Freddy.T

Their room consisted of two desks facing the windows over looking the common, closets on either side of the door and bunks with storage drawers under them.They had to walk all the way down the hall to the bathroom and showers.

It took them a little while to get used to each other.They had been placed in the same room because they were both majoring in Civil Engineering. They both had dreams of building bridges and roads in some exotic places like Australia.

They were both kind of shy around each other at first.They would not even look at each other while getting dressed in the morning or as they got undressed for bed.

Freddy was a normal boy.He had discovered the joy's of wanking when he was about 12-years old. He didn't do it in their room for fear of being caught for the first few weeks.He had tried dating girls in lower school and did not like them.

One was all over him wanting him to stick his fingers in her pussy and lick her pussy before he could fuck her.When he put his finger in her pussy he could smell it and he thought she stank.He almost vomited when she stuck her pussy in his face begging him to suck her pussy.He was not even able to get a boner so he never fucked her.Then one of the older boys in school became his friend.

This boy was a couple of years older.He introduced him to mutual masturbation.When they were wanking each other daily the guy taught him how to suck cock.He also sucked a few other cocks in lower school.It all seamed so natural.He knew that he would always prefer boys to girls.

As much as he wanted to find out if Charles would like his cock sucked he was afraid to broach the subject.The changing point came when Charles announced that he was going to the library to do some research.

Shortly after he left the room Freddy could not stand it any longer and flopped on his bed after pulling his pants and knickers down to his knees.He took his tool in hand and started wanking.When he heard the key in the door he could not get his pants up fast enough.Charles entered the room and saw him lifting his ass trying to pull his pants up.Of course he was fully exposed and erect.

He closed the door behind himself and said, "What a relief.I am a wanker too.I have been going crazy wanting to jack-off."

Freddy had never seen him doing it.They talked about it for awhile, rather nervously. Eventually they agreed to masturbate each other. Charles squeezed onto the bunk next to Freddy after he had pulled down his pants.They were both circumcised.They each took hold of each other's cock and started pulling on them.Freddy found out that Charles' cock was a little longer and thicker than his own.Charles didn't object when he leaned over his body and started sucking his cock.Charles returned the favor after he climaxed in Freddy's mouth.They started making it a practice of jacking- off and sucking each other every night after that.

Most of the other boys in the school went home on the weekends.Freddy and Charles parents lived to far away to make the trip very often.They opted to stay in the dorm on weekends.They had the floor to themselves on weekends.They could pretty much lounge around the floor naked if they chose.

They could sleep in Saturday.One such day Charles got out of his bed and mounted Freddy in a 69.They sucked each other until they came.When Charles sat up his asshole was rubbed against Freddy's face.

Freddy loved the smell and could not resist licking his brown hole.Not only Charles enjoyed the experience.Freddy found that he loved the smell of his asshole and reaming Charles.

It was only fair that Charles tongue fuck Freddy's asshole too.If he didn't enjoy it he never let on that he would not do it.

Later in the academic school year Charles proposed to Freddy that he allow him to try and fuck his asshole.Freddy was willing to try and they spent an entire Saturday experimenting with a variety of positions.Chuck would cover his cock with a lubricant and try to get it into Freddy's asshole but each time they tried it hurt too much.The way they finally got it in was for Freddy to bend over one of the two chairs and hang onto the arms of the chair and placed one knee on the seat.Charles stood behind him and held onto his hips as he thrust his hips forward.It hurt like hell until Charles started fucking him.

Freddy could not believe the way his own cock swung back and forth while being fucked.He had the largest boner of his life.All Chuck had to do was reach around and pull on it one time and Freddy shot his load of cum all over the seat of the chair.

It took a little time for Freddy to get used to being fucked but eventually he was able to take all of Chuck's cock any time they wanted to fuck.Freddy preferred to lay face down on the bunk with a hard pillow under his hips to elevate his ass for Chuck.

They had agreed to not cheat on each other and they didn't like condoms.They both thought it felt better without rubber.They like direct contact, skin against skin.

They did it sitting in their study chairs with Freddy facing him and with his back to Chuck. Freddy loves the feeling of Chuck's cum leaking out of his asshole.He reached between his legs and wipes his asshole so that he can taste Chuck's cum right from his own asshole.

It was Chuck's nightly habit to cum in Freddy's ass and leave it in there until it went soft and just flopped out.Freddy would take his spent cock in his mouth after he had just fucked him and suck him clean.He was in his glory when he could make Chuck hard again so that he could fuck him again.It was great to take his limp cock into his mouth and suck him until he had another raging hard-on.It was not uncommon for them to fall asleep with Chuck's cock in his ass after the second fucking.

They looked forward the weekends when they would have the place to themselves.They would only leave their room when they had too.One morning when Chuck was ready to go get something to eat and Freddy was being lazy he slapped with a leather belt him across the butt as he lay face down on the bed feigning sleep.He had doubled his belt before spanking Freddy.It was meant to be playful but it stung Freddy.

The strange thing was Freddy felt his cock come alive and it pressed against the cot hard. Freddy pleaded with Chuck to do it again.Chuck got a wicked look on his face and slapped Freddy's ass again, a little harder this time.With each stroke Freddy felt hornier.On the tenth stoke Freddy actually climaxed.Even Chuck saw the wet spot between Freddy's legs on the sheet.As Far as Freddy was concerned it was the best climax he had ever had.The thing that made it even better was Chuck mounted his red ass and fucked him one more long hard tiring time.

The first thing Freddy did was go out and buy them a cane.He selected one about a meter long.It was thin and flexible while being stiff.Charles was thrilled and after that on weekends he would punish Freddy.Freddy would bend over to present his bare bum and Chuck would start at the small of the back and lay stripes down his ass to the backs of Freddy's thighs.Just before Fucking Freddy's ass he would slap Freddy's scrotum.The first weekend he caned Freddy and fucked him between 6 and 8 times.The caning and fucking had been so thorough that Freddy had to take three days off from school.He could not lie on his back or sit in a chair.He even had to take his dumps squatting over the toilet.

Chuck tried to apologies time and time again but Freddy assured him that it had been the best time of his life. Over the years they had to buy a cane fairly often because after several months of use the cane would be frayed and limp if not broken.Canes just don't last that long.Freddy loves the swishing sound and the anticipation of the sting as the cane descends on his bum. A slap of the genitals and nipples also sends a thrill through his sexual organ.

They reserved the caning for the weekends when they had the floor to themselves.They vary the canings from severity from mild to hard between having anal sex.The two of them could manage 4 or 5 rounds of anal sex and canings.In fact Freddy got so he could not enjoy anal sex without being caned or at least having a leather belt stripping his butt.

Freddy is normally the recipient but sometimes as a variety Chuck would allow Freddy to cane him. Freddy developed a strong taste for the caning to start at the small of his back and work down his butt and the backs of his thighs to the knees.By the time the backs of his knees are turning red Freddy has had at least two orgasms.After his backside is bright red is when Freddy enjoys it the most when Chuck mounts him.Chuck likes a slow pace, taking long full strokes and never takes his organ out of Freddy's anus until he ejaculation and his cock looses his erection, it goes limp and just slips limply out of Freddy's ass.It takes about an hour for Freddy to recover afterwards.But then he is ready to start all over again.

Keeping the canings to just weekends kept their relationship from the other students but because they were so close there was always the joking speculation about their relationship.In the showers they would tease them about which one was on top. Freddy took the most teasing because he was the more subservient of the two.

Freddy and Charles are twenty years old now and about to finish their schooling.It seems almost impossible that they were never discovered but they managed to keep their classmates from conferring their suspicions.They have always had a monogamous relationship and never felt the need to use a rubber while fucking ass.

It came as a surprise to both of them when the head of their department invited them to him office during his office hours.He was very polite when he invited them to have a seat.It came as a shock when he confronted them about their relationship and what they planned to do after graduation.

They were dumbstruck to discover that he knew about what they had been doing for years on their weekends.He did not divulge how he knew.It was simply a statement of fact, without reproach.Then he shocked them by suggesting that they think about pursuing a teaching position with the school.