Back in 1995, the internet was relatively new and AOL ruled!!. Like everyone else back in the dial-up days I did much exploring. One of the things I discovered was the AOL chat rooms and Newsgroups. I have been an enema addict since childhood and before this new way of communications was introduced, it was almost impossible to communicate with like ladies that shared mutual interests. Well anyway, I found a chat group if I remember correctly, it was E-SIG2CHAT. I felt like I was in heaven!!!. So many other people shared the same. I met this fine lady, her name was Donna. She lived in New Jersey and I was in Brooklyn. After countless conversations with limited access to photo sharing I took a chance in meeting Donna. We conversed on the phone and settled on a date to meet. We met at a diner in Rockaway, NJ. It was a cold March morning with a freezing rain starting to fall as I left. Driving about forty miles in Interstate 80, I reached the location. Waiting in my car I saw Donna pull up in her mini van. I walked over in the now falling snow with a bouquet of flowers for her. What a surprise !!!, Donna was about fifty five, with lightly grey hair and about two hundred and twenty pounds. She greeted me with a nice smile and the flowers made her very happy. She was very excited that I drove that far to see her. She was just divorced after a twenty year marriage. She asked me if I had brought any "toys" with me as she enjoyed seeing other peoples equipment. I said yes I did. She said follow me I have a nice place to go to. As she lead the way, the snow became heavier and the temperature was dropping. I followed her about ten minutes arriving at this older house. As we walked up to the door she explained that this was her dad's house and he had passed away about a year ago. She said that this is where she grew up and had been given many enemas and spankings. That information made me stand at attention immediately. We went into the house and sat down in the living room. The heat was not really on and the house had a musty smell to it but it was clean. After we broke the ice, Donna then had me stand up and place my hands on my head and turn around, doing a 360. Very nice I see, sit down again. As I sat down she went and brought out "her toys" and laid them out on the couch. I did the same but I will admit, she had many more bags and nozzles along with about six different wood paddles. She asked me how I was interested in enemas and discipline. We had spoken before that I was spanked as a kid and received many enemas from my aunt. At first, I hated them but as I got older, I took the enemas and spankings as a show of affection. I admitted that I totally loved being in the presence of a mature, strict and stronger lady. Donna then admitted that she was the oldest and she had four half brothers and she also helped raise them. I was about thirty five at this time and she said that I reminded her of the youngest half brother.

The conversation the returned to our different "toys" . Then she pulled out a bottle of liquid glycerin and said with a wicked smile, this is for you!. At the time I did not know what it was for but I soon found out. Donna was asking me at length on how I was spanked and for what as well as how many enemas I got in a month, if the water was warm and very soapy. She also was curious if I was given enemas in front of others. The conversation was getting me very excited. She explained that she was the oldest and had helped her dad to raise her four half brothers because her dad's second wife passed away and left dad with the four. I asked Donna how she helped in raising them. She helped with the school work and such then she also said she was the disciplinarian to them. She had no problem spanking them and also giving them enemas. Dad was always working and left much up to her judgment. Donna had a smirk on her face when she said that I reminded her of her youngest half brother and she will treat me as such. Then Donna got up and opened the dresser drawer and removed a paper bag and reached in the bag and took out a 2-pack box of Fleet disposable enemas and said these are for you. I never had been administered a Fleet enema before.

Then all of a sudden Donna's demeanor changed drastically! She said that she was going to call me Joey, her youngest half brother's name. JOEY !! Take off all of your clothes ....except for your underwear. As she said this, she reached for one of her paddles that were with her toy collection. She said it in such a way that I knew if I did not listen to her, whatever she was planning to do to me would be much worse !!!!. I quickly disrobed and waited for her next command. Donna looked quite pleased and left the bedroom. I was standing there in my white briefs, admittedly very excited as the bulge in my underwear communicated that. Donna came back into the room changing from the pants and shirt to a pale blue house dress. Donna then sat down on the foot of the bed and pulled her dress up exposing her thick legs then reached out and took hold of my arm pulling me across her ample lap. I was laying face down across her lap starring at the green carpet. Then she pinned my left arm to the small of my back and then she wrapped her right leg over my legs to keep me in position. I was there for about a minute before Donna spoke a word. Then I heard her say JOEY, DO YOU KNOW WHY YOU ARE HERE IN THIS POSITION? You were a bad boy and I have warned you as to what I would do to correct you. You will not be able to sit for a week.................... I felt her move slightly and I tried to see what she was doing then her paddle raised high came crashing down across both buttocks. She chose an oval oak paddle that was three quarters of an inch thick and about eight inches wide. I jumped at the first of about twenty five strikes she gave to me. The thin material of the briefs did almost nothing to cushion the blows. Then she stopped and put the paddle down. I was welling up from the stinging pain, Donna didn't say anything to me then I felt her fingers go between the skin of my back and the elastic band of the underwear..........and with one motion, she pulled them down to my knees. NICE, you reddened up so nice. As I laid there I felt the cool air of the room on my very hot buttocks. Then Donna started to spank like a machine. First with her hand then with the paddle!!!. She must have laid down a hundred spanks that had me crying like a baby. She was a strong lady and was able to hold me in place for the entire spanking. After a while I couldn't feel the stinging pain but it did feel like nothing I ever felt before. Between the sting of the paddle and the pressure on my hard penis against the bare skin on her legs, I came on her lap. Also ad Donna spanked me her breathing was faster and deeper until she herself shook uncontrollably and only after that did she stop spanking me.

After Donna released her iron grip on me I meekishly lifted myself off her lap. Donna then said you naughty little boy, you made a mess on my lap and for that I will clean you up..........INSIDE AND OUT !!!!!!!!!!!!. ON THE BED ASS UP !!!!!!!!!. Then she pulled my briefs off completely. I was on all fours when Donna started to run her fingers all around my hot well spanked ass then she in a trance like voice was repeating ASS WHAT A BEAUTIFUL ASS then she started to kiss my buttocks then she slid her tongue all around then into my rosebud. She did this for about ten minutes when she suddenly got up and went to the bag. Then she removed the 2-pack of Fleet enemas. EYES FORWARD then I heard the sound of a cardboard box being open then the sound of a plastic cap being snapped off. Then I felt the very cold nozzle of the Fleet enema penetrate my rosebud then the cold liquid squirt into my ass. She left the nozzle inside me about thirty seconds after the last of the enema was in me then she pushed my ass forcing me to fall face first onto the bed. Then Donna climbed onto the bed and laid next to me. She was making small talk saying that she didn't want to spank me but she had no choice. She kept me there until the enema did it's job and I got up and ran all the way down the hall to the bathroom. There was no door on the bathroom and when I was on the toilet I can see Donna get her red open top enema bag and was assembling it. She had such a sadistic smirk on her face. She knew full well that I can and was seeing her every move from where I was sitting still releasing the Fleet enema. This enema bag was not the one she had already laid out on the bed. This time she went to the dresser drawer and removed this box. After opening the box she pulled out this red large as in four quart open top enema bag. She lifted it up to her face and inhaled deeply, the scent of old rubber and did this for about a minute. Then she reached for the red coiled hose and pulled it so it was straight and she laid it on the bed. Then she picked up the old fashioned stainless steel pinch clamp and carefully slid the hose on to the clamp. Then she attached the hose and clamp on to the black nipple that was on the bottom of the bag. Then she laid the bag on her shoulder and reached for this black old fashioned douche nozzle. This one had a slight bend in it and she screwed it on to the hose. Then I saw her close the pinch clamp and it made a metallic snap sound. Then she put the completed bag down on the bed and sat at the head of the bed......... waiting for me. I was finished expelling the Fleet enema and she yelled out, "Wash yourself, I don't want to see any mess". I got off the toilet and picked up the wash cloth and opened the faucet to get the hot water running. It was very cold at first then it got hot. I wetted the wash cloth and cleaned up with the bar of soap that was there. After drying up I started the journey down the long hall to where Donna was. I walked into the room and at Donna's right side was this rectangular paddle. Donna looked up and our eyes met again. Come here Joey as she reached out for my arm. Donna picked up her dress again exposing her ample lap. She pulled me over her lap wedging my manhood against her very warm lap. This time she just secured me close to her with her left arm as she picked up the paddle and spanked me for about five minutes. This time the spanks were more to keep my buttocks nice and red. I was almost ready to cum on her leg when she stopped spanking me. Then she released her grip on me and let me up. I was rubbing my stinging buttocks when she got up and picked up the big enema bag she just assembled. Along with the bag she also picked up the bottle of liquid glycerin then took me by the hand and led me back to the bathroom.

Joey, I want you to see just how I am going to prepare your enema, the special one with my special enema bag. This is how I prepared my half brother's enemas. Standing by the sink, Donna opened the hot water valve then the cold water valve. What I did not notice at first was the long 'J" shaped spigot on the sink. It looked like an inverted "J". This made it real easy for Donna to fill the large enema bags she had. Ahhhhh Nicde and warm, just the right temperature. She filled the bag up to about three and a half quarts of warm water. With the faucet still running, she opened the bottle of glycerin and poured about six capfuls of glycerin into the bag and added more water. With the bag almost full, she shut off the water and held the bag over the sink with one hand and then took the new bar of Ivory soap and slipped it into the bag. She held it there for about five minutes and the enema water turned so white, it looked like milk !!! . Then she got a hold of it and put it back into the soap dish. GO AHEAD INTO THE BEDROOM I will follow you. I walked there completely nude with a very bright red buttocks. Donna followed me in and she said your buttocks are as red as this enema bag !. When I got into the bedroom, I glanced in the mirror to see Donna holding the bulging enema bag in one hand and the hose and nozzle in the other. She looked SOOOOO FUCKING HOTTTTT. Then I also saw my fire red buttocks. And did they sting.

OK Joey, on the bed ass up !!!!. I climbed up and as I did that Donna hung the enema bag from the hook in the wall about three feet above the bed. Donna then delivered about a dozen open handed spanks to my ass again. Then she stood there for a minute then she yelled out EYES FORWARD OR ELSE !. Then I felt her fingers parting my well spanked buttocks then the douche nozzle resting at my opening. Then she slid it into my ass without any lubrication causing me to jump. VERY NICE, I DON"T WANT THE NOZZLE TO SLIP OUT AS YOU TAKE YOUR ENEMA. Then I felt the hose move as she picked it up then the "CLICK" of the metallic pinch clamp then the feeling of the enema start to run and fill me. At first the water was cool because that was in the hose then the very warm water from the bag !!! I started to get a raging hard cock from the warm water hitting my prostrate gland then Donna started to move the nozzle in and out then around. The feeling, I can't describe it other then pure pleasure ..........Then the first of many cramps. DONNA, PLEASE SLOW THE ENEMA FLOW DOWN..........Oh the cramps...................... JOEY that is part of the punishment. If you complain again I will really paddle your ass and DON"T HAVE AN ACCIDENT. Oh how I struggled taking the four quart enema, I was begging Donna to at least slow down the flow then she took pitty and using her hand pinched the hose to give me little relief. I was cramping yet the excitement gave me such a hard cock !!!!. Then with the hose still in her hand she grabbed it and with the other pushed in my stomach giving me such cramps. I struggled with the soapy glycerin enema inside me but I was able to take the entire four quart enema !!!!!!. With that I heard the pinch clamp being closed then Donna removed the nozzle from my ass and I RAN down the long hall to expel the enema. As I expelled the enema, I was dripping pre cum all over. I was there a good fifteen minutes before I can even move from the porcelain throne. Donna walked in and said WOW HOW RED YOUR FACE IS as I finished up the enema. What I did not see was Donna bringing back the empty enema bag then refilling it with this time a very cool water !!!. She said that this is how she gave enemas to the half brothers and how such I remind her of them. "DON"T WORRY JOEY, I AM GOING TO WARM YOU UP WHEN YOU GET THIS COOL WATER ENEMA" I asked her how is she going to do it? This time I will use VICKS for the lubricant !!! I want to see you jump around but this time you will be over my knee so I can use the paddle on your ass as you get filled and she said this with a smile. I cleaned up after expelling and donna had the bag filled already then took me by the hand back to the bed room. She moved closer to the hook in the wall and hung the again bulging enema bag on the hook. Then she went over to the chest of drawers where she got the enema bag from and took out this bulbous black nozzle. It had a thick end and a long shaft. She pulled the douche nozzle off the hose and replaced it with this thick nozzle. True to her word, she had a large jar of Vicks Vapo Rub on the bed. She sat down on the bed, again lifting her dress up to give me a bare skin lap to lay on. Over her knee I went, this time I was on a true ninety degree angle my head almost upside down and being almost parallel with her ankles. The smell of Vicks was filling the room when she put a glob on her fingers and coated the nozzle with it then she slid her two fingers in deep into my ass, stretching the hole to accept this big nozzle. Then all of a sudden my ass started to burn causing me to wiggle and move while on her lap. Donna enjoyed the "Lap Dance" causing her to breathe rapid and deep. Then I felt the coolness of this big nozzle rest at the opening of my rose bud then she said .... TAKE A DEEP BREATH and as I did, she pushed the nozzle in deep in one shot. The pain was deep but it also felt good along with the menthol burning at my opening. "I want you to get used to the nozzle" then she started fucking my ass with it then the metallic "CLICK" then the feeling of cool, very cool water fill my insides. Your ass looks so good with the nozzle and hose peeking out from between your cheeks. The water was rapidly filling me as Donna kept moving the nozzle in and out causing me to shake uncontrollably and to ejaculate on her lap leaving another mess.

Joey, you are such a bad boy making a mess on my legs, Donna exclaimed. You will HAVE TO BE PUNISHED for this. After the enema bag went flat I heard the usual "click" and she shut off the water so the enema wouldn't back up in the hose. Without warning, Donna took her left hand and pushed down on the small of my back to create more pressure on me to make the enema that churned inside me !!!!! Oh Donna, the cramps are so bad, I don't think I can hold the enema anymore !!!!. ""Oh, Joey, you will with that big nozzle so tightly fitting in your ass"" Then she kept up on the pressure making me squirm more on her lap. After about five LONG minutes, Donna said get up and stand there. I did get up as did Donna. As she stood up, I saw my cum run down leg. Then Donna went over and took down the flat enema bag and handed it to me and said go to the bathroom !!! I ran off to seek relief. After releasing the soapy enema, I was there in the bathroom about fifteen minutes. I cleaned up and came out only to see Donna this time in the nude wearing this long strapon !!!

Now Joey, for the second part of your punishment, I am going to fuck your man-pussy with my favorite strapon.!!! AND YOU WILL TAKE IT ALL !!!. I want you to look at it and know that this will be inside you as long as I want it to be inside you. Now, I have a "special treat" in store here. Now Joey, Get on the bed on all fours, ASS UP!!!. Yes Ma'am I answered and climbed up as she said. NOW, EYES FORWARD, you are NOT to move your head and look around. Then Donna left the room and I heard her going down the stairs. I thought to myself "WHAT'S GOING ON?" Here I am butt naked on all fours with still a red ass. I started to catch a chill from the cool air then I hear Donna coming back up the stairs then a SECOND set of steps. Donna enters the room and the first thing she said was KEEP YOUR EYES LOOKING FRONT. After about a minute I hear "turn around and look at me" I turned my head and see Donna now wearing her strapon snugly in it's harness. Standing at her side was this other lady !!!!. Joey, this is Susan. I invited her to watch as I administer the second half of your punishment. She will watch as my strapon slowly and deeply penetrate your man pussy !!!! After I have my way with you and you are totally fucked, I will sit here and watch Susan take you across your lap and give you a good spanking and if she likes, give you a couple of enemas too. I was totally humiliated knowing this lady was also viewing me naked and all open. I could see by the expression on her face that she was paying special attention to my bare red buttocks and my man-pussy. Then Susan said with excitement in her voice oh yes Donna I LOVE to give naughty boys enemas and spankings !!!!. To be continued.