ANAL FOR JENNAI’d by accident come across spanking sites on the internet and had realised that I had a repressed need to spank women, if not more. I registered with a site that had taken my fancy and soon I was a regular posted, on the ‘Off Topic’ forum. There was also a site chat room and I was a regular visitor. After a short time some of the ladies in the chat room was speaking to me in ‘private chat’. I was surprised on evening when after on such private messaging session the woman who was called Jenna asked if I would like to meet. We arrange a day and time and chose a ‘vanilla’ venue - which was a coffee shop close to her home. We soon became spanking partners, even though she was married. Her desire for spanking had been evident since she was thirteen; it had taken over thirty years for her to realise her needs. We met whenever we could, and soon I had built up a collection of spanking implements and the sessions where quite prolonged and after at least an hour of over the knee spanking and paddling would progress to a severe caning, often with over 150 strokes. Jenna during these session had admitted that she also had started reading various spanking and fetish magazine, which her husband strangely bought and enjoyed but did not practice in real life; much to Jenna frustration. After she had visited a BDSM fair one weekend she had told me of some of the items that given her a sexual tingling. These included various bondage cuffs and straps, and in particular some silicon butt plugs and an enema kit. Taking note I visited a fetish supplier ‘on line’ and bought some of the items Jenna had talked about with what could only be described as lust. They arrived surprisingly quickly and i took them to our next meeting. As usual after our initial spanking, where she was over my knee, with her skirt raised and with her panties around her ankles, Jenna was excited and had a wet pussy. As I was caressing her bottom I was lightly brushing her labia, and as her level of excitement rose her pushed back to increase the pressure on her love lips.
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I reminded her about the items that had excited her at the BDSM fair. She remained quiet when I asked if she wanted to experience them or was it all talk. She did not answer, so I lent over to my bag and opening a side pouch removed a purple silicon butt plug.
It was one of the smaller ones, only about the thickness of a thumb and twelve centimetres long. It also had a distinct curve on the initial half of its length. As Jenna was laying over my lap she could not see what I was holding. Using her natural lubrication to coat the toy which was leaking from her cunt, I then placed the tip at the puckered entrance of her anus. I was surprised that it slipped straight in with little effort. Jenna let out a moan - not of pain but of pleasure. I fucked her arse with it, and she was soon cumming; in fact much quicker than she did when she had been finger-fucked. After she had recovered, I asked her if she still wanted to try an enema? She said that she did but was nervous to. As Jenna was somewhat submissive I took the lead, and picking up my bag, told her to get up the stairs and go into the bathroom. I laid some towels on the tiled floor, and told her to take her clothes off. While she did that, I took what I needed out of my bag. As Jenna was now naked I told her to lay on the towels and to lay on her left side.
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I was now filling an enema bag with warm water at 40°C using a digital thermometer to check. I knelt next to her, removed the butt plug and lubricated her sphincter, then eased the rounded tip of the tube which ran from the filled bag in. The bag was hanging from the rail of the shower curtain. I reached up and opened the valve at the base of the bag and the fluid started to fill her. As it was her first time, I had only put 1½ litres in the bag. When it had all entered her, I carefully removed the nozzle, and replaced the butt plug. After several minutes Jenna said that she wanted to let it out. I told her to hold the fluid for longer. I waited till she was very uncomfortable and told her she could sit on the toilet and remove the plug. She moved quickly and as she squatted over the bowl and jerked the butt plug from her hole. Once evacuated, she let out a cry of relief. I was unsure as to whether she had found it pleasurable or not but she had a big grin on her face, and looked contented. It had done something for her, just as the arse fucking with the butt plug had. As she sat contentedly she stared to finger her labia and then her finger were frigging herself. It had also been a big turn-on for me too.
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I was hard and so I pulled her on to the floor so that she was on all fours. I unzipped and kneeing behind her placed the head of my cock against her ring-piece and pushed forward, while Jenna realising what was happening pushed back in response. As her anus had been probed and stimulated I slipped in easily and was thrusting quickly, while spanking her arse simultaneously to add to the sensations she felt. Her tight orifice was really stimulating my cock and I was soon ready to cum. As I had noted earlier, Jenna came quickly too and as jets of my seed were released, she groaned and came too, then slumped on the tiled floor. We moved to the spare bedroom and I took my cane from the bag with us. We lay there recovering from the intense feeling of this new aspect of our fetish lifestyle. Jenna was surprised how much she had been turned on and how quickly she had come from the anal stimulation. Her husband had made it clear that he was not interest in any way in an such anal games; not even fucking her arse. As we lay there i was stroking and caressing the fleshy globes of her bottom. I was automatically giving her bottom gentle spanks. Then I told her to lie on the bed face down. I took some of the pillows and placed them under she abdomen, thus raising her bottom. Standing at the side of the bed, I placed the cane against her, positioning it. I now raised the rod and swung it up and then down across the fleshy globes.
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I continued, quickly giving twenty blows. These left several red stripes across her bottom. I continued, but stopped occasionally to stroke and gently rub the red and striped flesh. My finger tips felt the raised marks and some that where not so obvious. Jenna was becoming excited again and making sounds of being sexually worked up. As we were close n the one hundred strokes, Jenna was close to orgasm and then she was cumming. I continued to give more strokes and she came over and over again. Then she suddenly slumped forward, and was off in ‘subspace’. i stopped her caning and lay next to her and held her till she started to recover. It took a while for her to be able to speak, and she was weak and shaky for at least twenty minutes. I let her lay there and disappeared to make some tea and bought it back. We had that and then cuddled, and soon Jenna was asleep. I quietly collected up my bits and pieces, and kissed her goodbye, leaving her to sleep. Later that night we chatted on internet messaging. Jenna said it had been the most intense of our sessions so far, and thanked me for giving her a wonderful first anal experience and taking her into ‘subspace’.
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