My Neighbor's Son

My name is Shelly. I am 39 years old, married and I have an 18-year-old daughter named Connie. Three weeks ago my next-door neighbor and her husband were going out of town for a week and ask me if I would keep an eye on their house while they were away. Timmy their 18-year-old son would be staying home and they wanted to know if he could call me if he had any problems.

I told them no problem. I had watched Timmy and Connie grow up together since they were 2 years old. They stayed friends all the way thru high school and we considered Timmy part of our family. Timmy was a very trustworthy kid, so I didn't feel there would be any problems or wild parties.

Timmy had grown up into a good-looking young man over the last couple years and I was a little sorry Connie and him were just friends. He was about 6 feet tall 155 lbs. Kind of on the skinny side and he always seemed very shy.

It was about 11 p.m. on Sunday night, two days after our neighbors left that Timmy called. He said he was moving some boxes and tripped over something. He landed on his backside and was in a lot of pain. I told him that I would be right over. I always sleep in the nude so I quickly threw on a robe and ran next door. I used my spare key that Timmy's mother gave me and let myself in. I yelled for Timmy and heard him call back to me from the kitchen.

As I got to the kitchen, Timmy was lying in the middle of the floor with nothing on but a pair of boxers. He explained that he was getting ready to go to bed, when he decided to move a box of books out to the garage and tripped over the chair. He landed right on his butt and the books came crashing down all over him. He had a terrible shooting pain in his butt and lower back and was having trouble moving.

I told him that I wanted to take him right to the hospital and have him checked out. I went up to his room and grabbed a t-shirt, robe, and a pair of slippers for him to put on. When I got back downstairs, I put his one arm around my shoulder and my arm around his waist to try and help him to his feet. As we started to try and get him up the tie on my robe had loosened a little and as we lifted my robe bunched opened and my right boob popped out.

There was nothing I could do to cover myself up without dropping Timmy so I acted like I hadn't noticed and I kept lifting. By the time we had gotten him to his feet and leaning against the table the whole front of my robe had come open. Timmy was not only staring at both my tits but he also had a bird's eye view of my shaved pussy. (I love the feeling of a clean-shaven pussy and had always kept it shaved since college)

I acted like I hadn't notice that my robe was open and gave him a good long look before I turned and pulled my robe shut. When I turned back around Timmy didn't look directly at me but I could tell him enjoyed the view from the developing bulge in his shorts. We walked slowly to the car, where I left him and ran into my house to throw on some clothes. Since I was in a hurry I just threw on a pair of loose shorts (no underwear) and a t-shirt (no bra) and ran back down to the car.

When we got to the hospital, they took us both into the examination room. A pretty blonde hair nurse came in and started taking down Timmy's information. She told him to remove his robe and shirt and put the hospital gown on. She told him he could leave his boxers on and the doctor would be in shortly, I saw a sigh of relief cross his face. Timmy was lying on the table on his side with his back to me when the doctor finally came in. Her name was DR Morrow and she appeared to be in her late forties. She was attractive with shoulder length black hair, a dark completion, and what appeared to be a very nice figure. She started looking over Timmy's chart and the x-rays that had been taken. She walked over to the examination table and had Timmy remove his gown. She told him to lye back down on his side while she examined him. The doctor started pushing on his lower back and asking him if it hurt. Each time Timmy would answer no and the doctor would move her hands lower, push and ask him again if it hurt. This went on until she got to right above Timmy's butt.

Once she reached his boxers she took her 2 fingers hooked them on either side of his underwear, told Timmy to raise himself off the table a little and she started pulling down his boxers. She pulled them down all the way to mid thigh. I had to turn my head away. Where I was sitting I was staring straight at Timmy's bare ass. I was about 3 feet away and at eye level. Poor Timmy had to be dying of embarrassment, not only of being exposed to this lady doctor but also his next-door neighbor. The doctor continued pressing on his lower back, upper butt until she got to about an inch from Timmy's puckered asshole and he let out a scream.

The doctor quickly stopped pushing and told Timmy he could pull his boxers back up. She than told us he has an internal bruise of the anal muscle. It is about 2 inches inside and up from the anal opening. It was nothing serious as long as it was treated. "I'm going to write you 2 prescriptions that you need to take for the next couple of days. I am also going to give you something right now that will help you with the pain" said the doctor. She went over to the counter, grab a pair of gloves and told Timmy to get down from the table. I knew what was about to happen and I started to get up to leave and the doctor told me that wouldn't be necessary so I sat back down.

The doctor had Timmy stand about 3 feet from the examining table with his feet shoulder with apart she than told him to lean forward, putting his weight on his elbows. Now Timmy being 6 feet tall when he leaned forward his ass was sticking straight up in the air. I think at this point he realized what was about to happen.

The doctor took a hold of Timmy's boxers and in one swift motion pulled them down to his ankles. She had him lift his one leg out of the boxers so he was able to spread his legs wider. At this point Timmy was bare ass naked. With the exception of facing the table his entire body was on display. It was at this point when I felt a tingling between my own legs. I was getting so turned on I could feel my pussy juice start to soak my shorts and now I wish I had put on underwear when I had gotten dressed. I was sitting directly behind him and I could see right between his legs. I was looking directly at his balls and penis hanging down. It had been almost 20 years since I had seen another mans penis besides my husbands and here I was looking at my daughters best friends. My husband's penis looked tiny compared to what Timmy had between his legs. It hung straight down about 8 inches and was about twice as thick as my husbands. I was so turned on I thought for sure the doctor would smell my sex in the air. If she had she didn't act like she noticed.

The doctor told Timmy to take a deep breath and relax. She stuck 2 fingers into ajar of Vaseline and smeared it up and down the length of her fingers and over the entrance to Timmy's virgin asshole. She slowly started pushing her fingers up and into his ass. Timmy rose up on his toes from the pressure until the doctor had both fingers buried up to her second knuckle in his ass.

She began sliding her fingers in and out a couple of times loosing up his ass. As quickly has she put them in she took them out. Just as Timmy was about to get up the doctor told hi m to stay put that they were not done yet. She than grab something that looked like a suppository, (about the size of full roll of life savers) and began greasing it up. The doctor took her free hand and spreads Timmy's ass even further. She positioned the roll at Tim's asshole and started to slowly push. She would push a little bit and than wait a few seconds and than push some more. This went on for about 3 minutes before the entire roll disappeared in Tim's ass. She than took 2 fingers and worked there way up into his ass and started moving them in and out. She explained that his would help the medicine dissolve and it would start to work quicker.

Tim started to squirm from side to side but really could move because of the position he was in. From where I was sitting all I could see was the doctors fingers moving in and out of Tim's ass. I heard the doctor tell him "that's ok. That usually happens and that it actually helps." I was sure what she was talking about until she withdrew her fingers and stepped to the side. I than realized why Timmy was squirming, other than having 2 fingers shoved in and out of his ass, his dick was fully erect and sticking out like a torpedo. It had grown to over 10 inches and was hanging down between his legs for the doctor and me to see. I couldn't even imagine how embarrassed Timmy had to be.

I don't know how the doctor did it. She was very professional and told Tim not to be embarrassed that she was a doctor and had seen a 1000 naked man before. Somehow I don't think this comforted Timmy too much.

The doctor went on like nothing was different and told Tim to try and relax they are almost down. With that she shoved her 2 fingers back up into Timmy's ass, catching him off guard because he let out a little moan, and continued pushing them in and out. She than shifted herself to the side, giving me a birds eye view, and with her free hand she reached around and took hold of Timmy's erect penis. She started slowly jerking him off. She told Timmy that this helps the prostate muscle expand and contrast and would help the bruise heel faster.

This was too much for me to handle. My own juices had already soaked thru my white shorts and started dripping down my legs it had left a stain in my crotch. It was a good thing I had a long t-shirt on because it looked liked I peed myself. I knew for sure that everyone in the room could smell my sex and if I touched my clit I would come within seconds. I don't ever remember being this turned on before.

In only about 30 seconds Timmy's breathing quickened, and Dr Morrow started pumping both hands faster. Timmy finally let out a loud moan his legs buckled and he started shooting his load onto the floor and doctors hand. I doubted this was the first time Timmy masturbated but I am sure it is the first time someone jerked him off with 2 fingers up his ass while his neighbor watched.

The doctor withdrew her fingers from Timmy's ass and went over and stared cleaning her hands in the sink. She handed Timmy a towel so he could clean himself off. She told him that he is going to be sure for a couple days to stay in bed as much as possible and to make sure he finishes his prescription. Timmy pulled back up his boxers, pulled his shirt on and put his robe back on. We left the hospital without saying a word to each other or making eye contact. We drove home in complete silence. I think neither one of us new what to say. When we got to Timmy's I helped him into his house and up to the bedroom. I thought the best way to handle this was to act like it was no big deal and told him not to be embarrassed about what happened tonight. That I was a grown women and that he shouldn't give it a second thought. I told him that if it made him feel better this would be just between us two. Timmy finally spoke and said that would really make him feel better if we didn't tell anyone. I told him it was a deal and to stay in bed and I would pick up his prescription in the morning and bring it over. As we said goodnight his face was still bright red.

As soon as I walked in my house I went straight into my bathroom, grab my vibrator, pulled down my now drenched shorts and laid down on the floor. I stuck the vibrator about 5 inches up my pussy in one quick motion. My clit was swollen to twice its normal size. I withdrew the vibrator from my pussy and positioned the head off it at my ass. My husband had always wanted to fuck me up the ass but I would never let him. I never even thought about letting him do it but tonight I didn't even think twice about it. I started to push the vibrator in, I didn't have to worry about lubrication the vibrator was so soaked from my pussy that the juice was actually dripping down onto my hand.

It hurt a little bit going in but once I got it about 3 inches up my ass I just relaxed and the rest of the vibrator slid in easy. I turned the switch on and my whole ass starting tingling. With my free hand I shoved 2 fingers up my pussy and I started thinking about the doctor jerking Timmy off. I felt the orgasm building in my toes and up my legs. By the time I starting coming I was shoving the dildo in and at of my ass and finger fucking myself at the same time. I had to bite on a towel to stop myself from screaming and waking up everyone in the house. This was the best orgasm I had had in my life and I owe it to the 18-year boy next store.

To Be Continued...