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Shirley Miller's Sex Education Sessions

Session Two

It was 9:30 a.m. on Monday morning and I was expecting Jim and Anna for their second session. The doorbell rang, I answered it and it was Jim and Anna. They said hello and walked through the door and headed straight for the medical room. I closed the front door and followed them. Once inside the medical room I closed the door. Jim and Anna were already standing next to the long table where the clothes go. What a difference 90 days makes I thought. Anna was wearing a spaghetti strap sun dress with the bottom of the skirt well above her knee. What a change from the long dress she wore last time with the high neck. This time she was showing some skin. She and Jim faced each other and Jim gave her a kiss as he reached around behind her and unzipped the zipper on her sun dress. He stopped the kiss and stepped back and took the straps off her shoulders. The dress fell forward and she stepped out of it. He handed it to Anna and she folded it and placed it on the table. Jim placed his hands on her breasts and kissed her again. Anna was not wearing a bra as it was built into the sun dress. I also noticed that instead of wearing plain white granny panties she was wearing red bikini panties with lots of lace on them. Even I thought they were very sexy. Jim wasted no time in placing a finger in the elastic on each side and pulling her panties down to her ankles. Anna stepped out of them and she was standing there nude. Jim still had his polo shirt and jeans on. Anna gave Jim a kiss and lifted the bottom of his polo shirt and raised it over his head. She carefully folded it and placed it on the table next to her clothes. She then unbuttoned his jeans, lowered the zipper, and his jeans fell to the floor. Jim stepped out of them and Anna bent over and picked them up, folded them and placed them on the table. She then placed one of her fingers in each side of the elastic on his boxer shorts pulled them down. They fell to the floor, she bend over and picked them up and placed them on the pile of Jims clothes. She hugged Jim tightly as she kissed him. They broke the kiss and turned toward me. Anna said we are ready Shirley. Again I thought of what a change since the first session. I didn’t even have to tell them to undress. It seemed like they could not get undressed quickly enough and wanted to be nude in front of me.

I told them that this time Jim was going first. He look surprised but asked what I wanted him to do. I told him to come and get on the exam table laying on his stomach. He did as told and I extended the leg rest so he would be comfortable. I explained that this session teaches them some advanced sexual activities that some couples enjoy. The only way they will know if they enjoy them or not is to try them. So I told them we will start with taking Jim’s temperature rectally. This time it was Jim who screamed What? I said yes, it is the most accurate temperature and the prelude to anal play. I told Anna to come over next to me and I handed her the tube of lube. I told her to place some on Jim’s anus. She did and I handed her the rectal thermometer and told her to gently slide it into his anus, aiming towards his belly button. She did as instructed and soon the thermometer was 3 or 4 inches deep in his rectum with only the very tip showing. I started a stop watch and told Anna she could slowly and gently side it in and out and Jim might enjoy that. So she started a in and out motion and asked Jim if he liked that. He said he did. Without my telling her she took her other hand and started caressing his bottom. Jim told Anna he liked that and to continue. Soon the stop watch indicated 5 minutes and I told Anna it was time to take the thermometer out. She did and I asked her to read it. She said it was 98.6 or normal. I took the thermometer for Anna and placed it in a jar of alcohol.

I asked Jim if he was ready for the next step and he ask what it is. I told him a series of 3 enemas. He asked why 3 and I told him it took 3 to completely clean a person out. He said he was ready and I ask Anna to follow me to the sink. I turned the water on and asked Anna to adjust it until it was warm on her hand. She did and I opened a drawer and pulled out a new enemy bag and tubing. I took it out of the package and Anna said that seems big. I told her it held 4 quarts but I didn’t think either of them would be able to take 4 quarts today. I explained that they may need to work up to 4 quarts. I hung the bag on a hook in the wall and got a pitcher for Anna to put the water in. She filled the pitcher and I told her to pour it into the enema bag. She did as I told her. I then opened another drawer and got out a bottle of Dr. Bronners peppermint castille soap. I told Anna to hold it over the bag and squeeze a good amount into the bag. Again Anna did as I told her. I then took the end of the tubing, held it over the sink, and opened the clamp to letter the air out of the tube. I opened another drawer and took out a double balloon rectal catheter. It was also new and I had already attached the bulbs to it that inflate the balloons. I hooked it to the tubing. I then took the enema bag off the hook on the wall and hung it on the IV stand that was next to the sink. I asked Anna if she was ready to give Jim his first enema and she said yes. So I rolled the IV stand over to the exam table and had Anna hold the nozzle. I told him he needed to turn over and to raise his legs. I retracted the leg extension and he rolled over. I helped him put his legs in the knee crutches and had him scoot his bottom to the end of the table. I told him to lie back and relax. I put some more lube on Anna’s finger and told her to lube his anus up good. She rubbed the lube around his anus and I put some more on her finger and told her to lube the inside. She looked at me with a stern look but gently slid her finger into his anus. I explained to Jim that the nozzle is a double ballon one and that after Anna inserts the nozzle into his rectum that she will inflate the two balloons. First the inner one and then the outer one. I told him it will give him a full feeling in his rectum and ask if he was ready. He said he was and Anna proceeded to slide the nozzle into hims rectum. She had a hard time because of the size of the nozzle but after a few tries it slid in. So I showed her the bulb to inflate the inner balloon and told her to squeeze ti four times. As she started squeezing it Jim moaned. She stopped after 4 squeezes and I ask Jim if he was OK. He said yes. So I told Anna to gently pull back on the nozzle and then to squeeze the other bulb 4 times. She did and we could see the outer balloon inflate and pull tight against his bottom. Once again I asked Jim if he was OK and he said yes.

I told Anna to release the clamp and the water would start flowing in. She did and I told Jim if he needed her to stop the flow to just say so. I suggested to Anna that she should lightly caress Jim’s stomach area as the water flowed in. I took the tube of lube and put a large amount on Jim’s penis and told Anna he might like his penis stroked while the water was filling him. Anna eagerly took her other hand and started gently stroking his penis. Jim seemed to be enjoying this as the warm water filled him and Anna was caressing his stomach and stocking his cock. After a couple of minutes he told Anna she needed to stop the flow. He said he was having strong cramps. I told Jim that the soap causes he cramps and the cramps help to clean him out. I also told Jim to just relax and the cramps will pass. She closed the clamp and continued to caress Jim. After another couple of minutes he told her to continue the flow and she did. To my surprise Jim did not ask for the water to stop again and in a few minutes the 4 quart bag was empty. Anna closed the clamp but continued to caress Jim. After a few minutes Jim said he needed to use the bathroom. He said the cramps were worse. So Anna helped him get his legs out of the knee crutches and he stood up. I told Anna to follow Jim to the bathroom with the IV stand and with the nozzle in him. She did and when Jim was to the toilet I told him to kind of hover over the toilet and I told Anna to release the valves on both bulbs so the balloons would deflate. Anna then gently pulled the nozzle of Jim. Jim sat down on the toilet and I immediately heard water flowing into the toilet. I had put a chair in the bathroom and told Anna she could sit down and talk to Jim while he expelled. I rolled the IV stand out and closed the door so they could have some privacy.

About 5 minutes later they both came out of the bathroom and Jim said all the water is out. I told Jim that there was probably water still left in him and he should walk around the room for a few minutes and see. Sure enough in a couple of minutes he said he was cramping again and he headed straight to the bathroom and Anna followed him. She closed the door and they remained in there for about 5 minutes. They came out again and Jim said I think all the waters out now. I said fine you need to get back on the table. I told Anna to fill the bag again as before but this time with water only. After she filled it she put it on the IV stand, rolled it over to the exam table and she asked me for the tube of lube. She put some on Jims anus, some more on her finger, and inserted his finger in his rectum and moved it around. She pulled her finger out and ask Jim if he was ready. He said yes so she inserted the nozzle, this time like and experienced professional, inflated the balloons, and started the flow of water. She put some more lube on his penis and started stocking it with one hand and caressing his stomach with the other. Both Jim and Anna seemed to be enjoying this. This time it only took about 3 minutes for the water to fill Jim and when the bag was empty Anna stopped the flow. She continued caressing Jim. I told her to hold off making him cum at this time. Jim said he needed to go to the bathroom and Anna helped him out of the knee crutches and followed him to the bathroom with the IV stand. She took the nozzle out, brought the IV stand out to the medical room, put the nozzle in the sink and returned to the bathroom and closed the door. About 10 minutes when by and they came out of the bathroom. I suggested that Jim walk around the room while Anna filled the bag again. Soon Jim was headed back to the bathroom while Anna continued filling the bag with plain water. When Jim finished he once again climbed onto the exam table, put his legs in the knee crutches, and told Anna he was ready. Anna repeated the process as before until the bag was empty and Jim said he needed to use the bathroom. After Anna took the nozzle out, she remained in the bathroom with Jim and I took the bag, nozzle and IV stand out and closed the door. I began washing the nozzle and disinfecting it so it would be ready for Anna. This time they came out of the bathroom and Jim just started walking around the room. In a few minutes he headed for the bathroom again. Soon he was out and said he was empty. I told him to get back in position on the exam table and he did. I had Anna come over to the sink and I showed her three lube shooters and had her fill them. We then went back to the exam table and I had her lube Jim’s anus. I showed her how to insert a lube shooter and empty it into Jim. She then did the other two lube shooters. Jim asked why so much lube and I told him so the dildo would slide in easily. I then opened another drawer and got out a strap on harness with a medium sized dildo on it. I helped Anna put the harness on and she walked over to the side of the exam table so Jim could see it. Jim liked Anna with the harness and dildo on. I explained to both of them that Anna was not going to peg Jim today as I thought that should occur with just the two of them as it was very personal and I thought it should be private. So I showed Anna how to take the dildo off the harness and she got out of the harness. But I told her to gently slide the dildo into Jim and gently slide it in and out. As she did that I squeezed some more lube on Jim’s penis and suggested to Anna that she should stroke Jim’s penis until he climaxed. So she was moving the dildo in and out of his rectum while stroking his penis and in just a few minutes he came spraying semen all over his chest just like the last time. Anna ask Jim if he liked that and he said yes. She took the dildo out of Jim, walked over to the sink and got a wash cloth and put warm water on it and them came over and cleaned jim’s chest, penis, and anus. So Jim got up from the exam table, hugged and kissed Anna and said it’s your turn now.

So Anna got onto the exam table and put her own legs in the knee crutches. Since she had been in that position on the exam table several times she knew how to position herself now. She also slid her bottom down to the end of the table. Jim told Shirley that he had observed every detail of the enema preparation so just watch me and correct me if I make a mistake. He got the thermometer and put some lube on Anna’s anus. He slid the thermometer into her anus and told Shirley to start her stop watch and tell him when 5 minutes was up. He put some lube on Anna’s clitoris and started rubbing it while moving the thermometer in and out. Soon Shirley said the 5 minutes is up so Jim took it out. He read it and was 98.6, normal just like his. He then hung the enema bag on the hook on the wall. He ran the water until he had the temperature just right and filled the pitcher with water. He poured it into the enema bag until it was full. He then held the nozzle over the sink and opened the clamp and let the air out of the line. He asked Shirley what happens if I forget to let the air out of the line. Shirley said nothing really, the air will go into Anna’s colon and it may cause stronger cramps. But it is best to get the air out of the line so she will have a comfortable enema.

Jim rolled the IV stand over to the exam table and took the tube of lube from Shirley. He put some lube on Anna’s anus and some more on his finger. He then gently inserted his finger in Anna’s anus and rolled it around and gently moved his finger in and out. Anna said that she liked that. Jim then took the double balloon nozzle and placed the tip next to Anna’s anus. He told Anna he was going to insert it now. He gently pushed on the nozzle but had some trouble getting it into her. He continued his efforts and finally it slid into her anus. He told Anna he was going to inflate the balloons now and he squeezed the bulb for the inner nozzle 4 times. Anna said Wow I feel full. Jim asked if she was Ok for him to continue and she said yes. So he gave a gently pull on the nozzle and then squeezed the bulb for the outer balloon 4 times. He could see the outer balloon inflate and it looked like it was placed properly for a good seal. He ask Anna if she was ready for water and she said yes. Shirley said wait a minute. Anna had a bad experience with enemas as a child and we want her to have a good experience now. So I want you to lower the IV pole about 6 inches. That will reduce the flow rate of the water and will be more comfortable for Anna. So Jim lowered it as instructed and opened the clamp. As he did he told Anna if she wanted him to stop the flow at any time to just tell him. He then proceeded to gently caress Anna’s stomach area while the water flowed in. All of the sudden Anna said stop so Jim closed the clamp. She said she was having strong cramps and they needed to pass before she took any more water. He continued to caress her stomach area and in a couple of minutes she said could continue so Jim opened the clamp. The water started flowing in again and Jim continued caressing Anna. After a couple of more minutes Anna said to stop I can’t take any more water. Jim shut off the clamp and looked at the bag. It was only about half empty. Jim looked at Shirley and she said we don’t want Anna to have another bad experience so take her to the toilet and let her expel the water. So Jim helped Anna get her legs out of the knee crutches, and followed her to the toilet with the IV pole and the nozzle still in her. Anna knew what to do. She hovered over the toilet and Jim let the air out of the balloons and withdrew the nozzle. Shirley had followed them into the bathroom and she took the nozzle and rolled the IV pole out of the room and closed the door.

In about five minutes they came out of the bathroom and Anna said I am empty. Shirley reminded her about Jim saying that. So Anna agreed to walk around the room for a few minutes and Jim started filling the bag again with plain water. After just a couple of laps around the room Anna headed for the bathroom. Jim followed and closed the door. They were only in the bathroom a short time when they came out and Anna said I’m empty now for sure. So she climbed up on the exam table and got in position. This time Jim put a bunch of lube on the nozzle and inserted into Anna on the first try. He filled the balloons and asked Anna if she was ready. She aid yes and Jim opened the clamp. Jim put some lube on Anna’s vulva and started caressing her stomach area with one hand and rubbing her clitoris with the other hand. As the water flowed into Anna, she started breathing faster, moaning, moving her hips on the table and soon there was an involuntary jerk of her body and then it was totally relaxed. Anna told Jim and Shirley I just had an orgasm. Jim said I know. Jim looked at the bag and it was almost empty. He said Anna if you keep going in a minute or so you will have taken the whole bag. Anna said fine and soon the bag was empty. Jim shut off the clamps, helped Anna off the table and they headed for the bathroom. Jim brought the IV pole and the nozzle out to Shirley and went back into the bathroom and shut the door. Shirley just sat down in a chair and waited. Soon they both came out and Anna said I know I am empty now, I expelled twice. So she climbed upon the table again and got into position. Jim followed the procedure and while Anna was having the third enema she had another orgasm, this one stronger than the first one. Again the flow was stopped, Anna got off the table, and emptied herself of he water. She then got up on the exam table again and into position.

Jim had filled the lube shooters and came over the the exam table and squeezed a good amount of lube onto Anna’s vulva and anus. He then one by one inserted the lube shooters into Anna’s anus and emptied them. At this Shirley stood up and came over next to Anna and Jim and said that she did not expect them to have anal intercourse here in front of her as it was very personal and should occur in private. She handed Jim the dido from the harness and suggested he use it on Anna as she had done on him and while doing that rub her clitoris to give her another orgasm. Anna spoke up loudly and said No Way. I want to feel Jim inside me right now. I know it is personal but Shirley you have seen every inch of both of our bodies, your have probed the insides of our openings, and you have watched us masturbate. You taught us how to have great sex. I want Jim inside me now and I want you to observe. Jim was hard as a rock and he moved toward the exam table. He said the table is too high and I can’t get my penis into Anna at that height. Shirley said wait a minute, and she went and got a small step stool and put it at the base of the exam table. Jim stood on it and it was just the right height. Jim placed his penis next to the opening of Anna’s rectum. Shirley told Jim to be very gentle as her rectum is tighter than her vagina. So Jim pushed very gently and soon the head of his penis was inside Anna’s rectum. Jim ask Anna if she was OK and she said yes, push your penis in further. So Jim pushed it in another inch or two. Anna said keep going I want your penis totally inside me and Jim eagerly complied. When his penis was all the way in Anna he stopped. Anna said I love the feeling and I want you to pump you penis in and out of my rectum while you rub my clitoris. Jim started moving his penis in and out and said Anna you are so tight this is wonderful. As he did that he was also rubbing her clitoris and it just took a couple of minutes and Anna had another orgasm. Jim could feel the spasms of her vagina on his penis and he kept up the strokes until he climaxed. Anna could feel the warm semen flowing into her rectum and said keep going so Jim did. But soon he stopped and they both just enjoyed the feeling of his penis in her rectum. But soon his penis started getting small and soon it totally came out of her rectum. Jim moved over to the side of the table and kissed Anna. It was a passionate kiss and it was obvious that their tongues were moving in and out of each others mouth. Jim was also rubbing Anna’s nipples while he kissed her. When they finally stopped kissing Jim went to the sink and got the wash cloth and put warm water on it. He washed Anna’s vulva and anus and tried to catch the semen that was dripping out. He also washed his penis. He then dried them both off with a towel. He put the towel down and went back and kissed Anna again. He stopped and told her he loved her that that was wonderful. She said she agreed. Jim asked Anna if she was ready to get off the table. Anna looked at Shirley and asked if they were finished and Shirley said not quite.

Anna remember that at your request I had your doctor send your birth control medicine to me. Yes I remember and I also remember it is now two shots. That is right Shirley said and that is because they improved the formula and it is now 100% effective. So I need you go get back on the exam table and lay on your stomach. When Anna got on the table Shirley extended the leg rest for her so she would be comfortable. Shirley told Jim that he might want to hold her hand and start massaging her back to relax Anna. Shirley went to counter and prepared the two injections. She told Anna that he new medicine is also thicker so it requires a larger needle, an 18 gauge one. She also has to use a longer needle, a 2 inch one because research showed that with a 1 1/2 inch needle the medicine was not all getting into the muscle. Shirley came back to the exam table and cleaned a spot on Anna’s left hip. Shirley then aimed the needle on Anna’s left hip and plunged it into her hip like a dart. The needle was all the way in her hip to the neck of the needle. Anna let out a little yelp and said it stung. Shirley told Anna that with the new medicine she had to inject it slower, taking 2 minutes per side. So Shirley started slowing injecting the medicine while watching the clock. Anna said this really stings and started sobbing. Jim tried to comfort Anna but soon she was really crying. Finally Shirley said the two minutes is up and pulled the needle out and put a bandaid on Anna’s hip. Shirley asked Jim if they could trade sides of the exam table and when on the other side Shirley cleaned Anna’s right hip. She then plunged the needle into Annas right hip and slowly started injecting the medicine. Anna was really crying loudly now and Shirley said she was sorry but there was no other way to do this. Shirley also told Anna that the benefits out weigh the pain. Anna screamed How do you know, the needle is not in your butt. But then Shirley said all done, pulled the needle out and put a bandaid on Anna. Shirley told Anna to just lay there, try to relax, and whenever she is ready she can get up. Take all the time you need. Anna laid here about 10 minutes and finally said she was ready. So Anna got up, hugged Jim, and they both headed for the table with their clothes on it. Anna stopped and apologized to Shirley for yelling at her during the shot. Shirley said don’t worry about it, I know those injections really sting. They stopped, hugged and kissed, and then Anna took Jim’s boxer shorts and handed them to him. Jim put them on. Anna then handed Jim his jeans and he put them on. Next she gave him his shirt and he put it on. Anna then hugged and kissed him again. Jim said and now you are nude and I am dressed. Anna said I wanted to be nude wth you longer. I love you looking at my body, I love you touching my body, I love you giving me orgasms and I don’t ever want you to stop. Jim told her he would never stop but she needed to get dressed so they could go home. Jim just stood and watched Anna as she got dressed. Jim thinks that Anna looks so sexy in the sun dress. When she was dressed they kissed again and turned toward Shirley and told her how great the session was. Jim said I think enemas, anal sex, and pegging will be a regular part of our sex life. Anna said definitely. Shirley said I am glad you enjoyed it so much. Frankly you two are the first couple to actually have anal intercourse here in my presence. Most couples accept my suggestion of using the dildo and wait to actually have anal intercourse in private. But Anna I understood your saying you just needed Jim inside you. And Anna I am so glad that the enemas were enjoyable and not painful. I had told you I would teach Jim to do that and I did. Shirley handed Anna a large paper sack and said the enema bag, tubing, nozzle, harness and dildo are in it. I cleaned them and they are a gift for you two. I hope you wear them out. You are all done and ready to go but I will miss you. You were both such good students.

They started walking towards the door but Anna stopped. Shirley you told us that this session would also include cunnilingus and fellatio and we didn’t do either of those. Shirley explained that as usual the enemas, pegging, and anal sex took up the entire time for the session. She said after the second session, I don’t charge for any further sessions. So if you want to come back for another session to cover cunnilingus and fellatio I will be glad to schedule and teach you those subject with no charge. A session for those two subjects usually lasts about two hours. Shirley said that some couples have preferred to have one session for each topic and the cunnilingus one usually last longer since women can cum multiple times. Anna said they would be calling to schedule another session soon and while she would discuss it with Jim, she thought they would want on topic per session. With that Anna and Jim both hugged Shirley and walked out hand in hand.