Teaching My Wife Ch. 04

Jack watched her intently and then started to get undressed. He stripped off his blazer, shirt and tie and then his shoes and socks. He stood close to the bed where Ann was preparing herself and took off his pants and underwear in one fell swoop.

Ann looked between his legs and said, "Oh my God." She later told me that Jack was not that long, only about six or seven inches but he was as thick as her wrist and he was not even fully hard.

"I can't take something that wide in my ass, it will tear me up," Ann said. Jack just smiled and said, "You really have no choice little lady now do you."

Ann knew he was right and resigned herself to her fate.

Jack pulled her off of the bed and got her down on her knees in front of him. Try as she might Ann could only get a few inches of his fat cock into her mouth and getting it into her throat was not going to happen. Jack let her lick and suck for a few minutes until he was rock hard and then led her back to the bed.

Jack said, "I know you are going to have a hard time taking my cock in your ass and I cannot have you yelling and carrying on so I am going to gag you because we cannot have a call go into hotel security now can we?"

Ann said she was almost in a trance as she heard his words but just could not respond. She watched Jack walk over to her bag and pull out a pair of her panties and one of her nylon stockings. She did nothing to resist as he forced the panties into her mouth and then tied them in place with the stocking. Ann now knew that her fate was sealed.

Jack then led her over to one of the plush chairs in her room and positioned her in front of it and told her to bend over. Ann did as he said and he told her she may want to hang onto the arms of the chair. She did as he suggested and gripped the arms of the chair tightly in her hands.

Jack then played with her ass forcing first one, then two and finally three fingers into her ass. Ann grunted and groaned with each new invasion of her ass.

He stopped playing with her ass and Ann knew the moment of truth was at hand.

Jack arranged his thick cock directly in line with Ann's ass and pushed forward. Ann tried to move away but positioned as she was against the back of the chair she had no where to go. Jack pushed forward and as Ann felt his cock slip through the ring of her sphincter she screamed in pain into her gag as she had never had anything so wide in her ass before.

"Get used to it baby," Jack said as he pushed another inch of his cock into her ass.

Ann said that she literally saw stars as Jack pushed the rest of his thick cock into her resisting ass. With Jack's balls resting against her Ann thought the worst was over but when Jack started to pull back she knew that was not the case. Ann said that she felt every excruciating inch as Jack sawed his thick cock into and out of her.

Ann whimpered into her gag as the invasion of her ass that she was powerless to stop continued.

Jack fucked Ann's ass for a few minutes and then when he felt her loosening up a bit reached around in front of her and started to finger her clit. Ann said that she responded almost immediately and started to fuck herself back on Jack's cock.

A minute or two later Ann exploded on Jack's cock and had a powerful orgasm that caused Jack to go over the edge and have his own climax.

Jack lay over the top of Ann for a few minutes and then slowly withdrew his softening cock from her ass. Ann told me about the popping sound Jack made when he withdrew from her ass and how her ass felt wide open for a few minutes after he pulled out.

Ann let Jack turn her around and kiss her deeply. He reminded her that this was not a one time thing and she murmured her response.

Jack got dressed and as he was leaving reminded Ann that if she did not want the tape of her activities disseminated that she would let him know whenever she was going to stay at the same hotel again so he could fuck her ass again.

I thought about putting a stop to Jack fucking Ann in the ass whenever she visited his hotel but decided that I could incorporate those sessions into her adventures and never did anything to stop it from happening.

I must admit that I continue to be surprised at how much and how quickly Ann had changed. It was as though the flood gates had opened and once she started fucking other guys she had no problem with getting kinkier and kinkier.

After her fourth adventure she even started to kid me about when I would come up with something that would actually be a challenge for her to do. I assured her that would not be a problem but that is a story for another day.