Ann’s Initiation

They met during their freshman year at Penn State, where during the first year they had to stay in a dorm, sharing rooms with students of the same sex. After a few dates, their sex life was limited to back- seat activities in Dave’s five year old Chevy, parked at a lovers’ lane. At the beginning of their junior year they decided to room together, with the intent of finally having a normal sex life instead of back seat fumbling. Ann was a slender, yet voluptuous, passionate girl of 5 ft 10, brunette, with great legs and an even greater round ass, normally “packaged” in tight fitting blue jeans. She had a flawless, somewhat Creole skin, probably inherited from one of her Italian or Hispanic grandparents. Just a guess. When she met Dave, she was a virgin with a strict Philadelphia Main Line upbringing, but was anxious to remedy this situation as soon as possible.

Dave, a 6 ft tall, athletic Pittsburgher, was most pleased to oblige and was looking forward to the delights offered by rooming with Ann. Nevertheless, their sex life during the first few months of cohabitation was somewhat inhibited. Ann was inexperienced and shy. Dave, who had much more experience, was concerned that if he revealed and acted on some of his sexual fantasies, Ann would find it weird, as did earlier his high school sweetheart. Their relationship broke off because of this. To put it simply, Dave liked enemas and would have loved to introduce them into their “repertoire”. In the meantime, he had to limit enjoying his equipment, hidden in his closet, while Ann went to classes. Satisfying though as this was, he yearned for a shared experience.

During lovemaking, he sometime casually touched Ann’s rosebud hoping for a positive reaction. Ann wished he would be more “intrusive”, but being shy, pretended not to notice these tentative fumblings. An accident was needed to break this impasse. In November, Ann came down with a cold and thought she had some fever. Dave went to the nearby drugstore, picked up a thermometer and handed it to Ann for using it. Ann looked at the instructions and blushing said: “This is an anal thermometer, I never used one of these”. It is unknown whether Dave’s selection was deliberate or not. In any case, he realized the possibilities and nonchalantly offered that he could take Ann’s temperature without a hitch. Ann, who also realized the possibilities offered by this situation, agreed.

Dave went to the bathroom and returned with a jar of Vaseline. He suggested that Ann lie on her stomach to facilitate the procedure. When Ann was ready, he pulled back the cover and pulled up Ann’s night gown, thus exposing her beautiful ass. Ann in her embarrassment hid her head in the pillow. “You ready?” asked Dave.

She mumbled, “Yes.”

Dave, using his thumb and index finger, spread Ann’s round cheeks and with his other hand smeared some Vaseline on Ann’s rosebud. Ann’s reaction was faster breathing and a slight upward movement of her ass, as if to invite penetration. Dave slowly inserted the thermometer and asked Ann if she was OK. Something like “mmm” came from the pillow. Realizing that there were five minutes to go (according to the instructions), Dave first twisted and flicked the thermometer, then moved it in and out. Ann moaned. Encouraged by this reaction, Dave massaged Ann’s crack, first behind and then in front of the thermometer, manipulated with his other hand.

Ann’s reaction was an “Oh!” and she spread her legs some, thus permitting Dave to reach her pussy which by now was sopping wet. He played with her labia and made excursions to her clit. Ann moaned and began to say “Oh, yeah.” Dave knew he was making positive progress. Repeating the massage and in-and-out technique, Ann reached orgasm in five minutes. It was time to read the temperature: 99F. Not too much but a clear indication that bed rest was desirable. Dave offered that he would procure some over the counter cold medication.

He returned in a few minutes with a box of stuff advertised on TV. The possible side effects warning, which neither of them read, included constipation. The next morning Ann complained that she was constipated and asked Dave to get her some laxative from the drugstore. Dave, the sly fox, immediately realized his good luck and objected that that would take another day to be effective. “I have a better idea,” he declared and proceeded to recommend an enema which would instantly solve the problem.

Ann, recalling the pleasant thermometer episode, mildly protested: “Wouldn’t that hurt?” Dave assured her that if properly administered, it could actually be quite pleasant. Questioning Dave’s qualifications to properly administer enemas, he lied that he had several during a hospital stay in his late teens. Nothing to it.

Thus, he trotted to the drugstore to procure the equipment, which of course he already had in his luggage. He bought a pack of Kleenex so he could come back with a credible package. Ann looked at him with anticipation and some anxiety. It would have been easy to allay her worries with a few kisses, but given her snotty condition this had to be avoided. Even lovemaking was a problem with facial contact. He therefore suggested to her to turn to the wall (so as not to see the proceedings) and said he will be back promptly to get the show on the road.

After retrieving his gear from its hiding place, he armed the bag with a medium size home made nozzle of 5/8 inch flexible rubber tubing 8 inches long, for greater extension and penetration. The “business end” conveniently narrowed to 1/4 inch for easy insertion. He filled the bag with warm water and took it, a butt plug and the Vaseline jar to Ann’s room. He hung the bag on the back of a high-back ladder chair and asked Ann, who was turned to the wall as instructed, whether she was ready.

“I am,” she said in a timid voice. Dave explained that pre-lubrication of the orifice is desirable. Again, he pulled off the cover, pulled up Ann’s night gown, patted on her fanny and suggested that she pull up her knees. The sight was exciting and Dave’s dick reacted accordingly. He then lubricated his middle finger and with a dab of Vaseline approached Ann’s anus, after parting her beautiful cheeks with the other hand. He put the dab of Vaseline on Ann’s rosebud with the immediate reaction of a sigh. Then he reamed her, with each circular motion gaining more penetration.

Ann said “Oh!” and moved her ass closer to encourage the procedure. Dave wiggled his middle finger in Ann’s ass and slowly shoved it in full length. Then he withdrew it some and repeated the in-out motion and wiggling several times. Ann’s reaction was a series of moans. Finally, he pulled out his finger and asked Ann if she was ready for the real thing.

“Oh yes,” was the anticipating answer.

He then generously lubricated the oversize nozzle and the butt plug. He inserted the 1 1/2 inch long narrow end of the nozzle into Ann’s ass and asked her if she was ready for the water flow. “I guess so” was Ann’s timid answer. Thus, he released the clamp and water began to flow. First, the water in the long tube was cool, but soon warmed up when it came from the bag.

“How are we doing?” he asked.

Ann said, “Fine, it is actually quite exciting.” Dave then pushed the nozzle further in, with its thick part further extending Ann’s asshole.

The reaction was immediate: “Oh, my.”

Encouraged, he slowly inserted the whole length with wiggling motions and with his other hand started to massage Ann’s crack behind and before the nozzle. Ann started to moan loudly. With her thighs closed, however, her pussy was not accessible. After about 1/2 quart of infusion, Dave set the clamp and suggested that Ann go on all fours, with her thighs spread. Ann readily obliged and Dave could continue the massage reaching to her labia and clit. When the clamp was again released, Ann seemed to be in seventh heaven. To delay her orgasm, Dave shut the water off again, with just 1/2 quart remaining, and limited the massage to her crack.

“Please don’t stop!” was Ann’s reaction. With the water turned on again for the home run, Dave continued the wiggly in-out manipulation of the nozzle and with his other hand concentrated on Ann’s labia and clit, now and then inserting a finger in her sopping vagina. Ann moaned loudly and started to scream as her orgasm approached. With perfect timing, Ann reached a formidable orgasm never experienced before just when the last drops of water entered her.

When things quieted down, Dave patted her fanny and slowly withdrew the nozzle, informing her that for good effect the water has to be retained for awhile. To facilitate this, he explained, a butt plug would be inserted. He then pushed the anal plug home, with another “Oh” from Ann. Dave suggested that she now turn on her back. He kissed her naked belly and proceeded to her bush. Ann spread her legs and Dave kissed and licked her clit, leading Ann to yet another arousal. This was another first in their lovemaking and Dave’s dick was hard as a rock. His balls ached. With his now free hand he inserted a finger into Ann’s vagina, while continuing cunnilingus. Because of this, and the warm water working in her guts, Ann had another orgasm the intensity of which she had not experienced before.

Dave announced that it was time to expel and sent Ann to the bathroom with the instruction to remove the plug just before sitting down on the john. He heard the gushing of water through the closed door. Ann cleaned herself and came back to bed glowing. She noticed Dave’s arousal and offered him relief. To avoid facial contact, this had to be doggy style.

Once again, Dave faced Ann’s beautiful ass offering two orifices for entry. Realizing that her anus was now clean and encouraged by Ann’s reaction to anal manipulations, he smeared some Vaseline on Ann’s now somewhat extended asshole and some on his penis for good measure. He then gently inserted the tip of his penis into Ann’s ass. Ann’s reaction was a sigh and the contraction of her sphincter gripping Dave’s dick, followed by release which Dave took advantage of by pushing his dick deeper into Ann’s ass. He reached under Ann’s belly and started to play with her clit and labia.

Ann’s reaction was a loud moan and another contraction of her sphincter. This made Dave withdraw some and when Ann’s muscles relaxed, he pushed forward again. A repetitive in-and-out movement started, resulting in a fantastic “milking” effect which brought Dave to the verge of orgasm. Luckily, Ann’s excitement also sky rocketed and she reached orgasm a third time just as Dave shot his load thinking that this was the most reliable birth control. Just a guess, he may not have been able to think at all in his ecstasy.

When things quieted down, he withdrew his now limp penis with Ann saying “Ooh” with regret. Dave cleaned Ann’s ass with a Kleenex, turned her over, kissed her belly, tucked her in and put her to sleep.

A couple of days later, Ann again complained of constipation. True or not, Dave more than willingly repeated the “treatment” with minor variations but not with less success. With these successful episodes a precedent was set. Dave now speculated how he could bring Ann to “return the favor.” He came up with an idea.

But that’s another story.