First Online Acquaintance

Here is the account of one of my first sessions. Some of the tone, like not using dialogue, is because she wants to be anonymous, and I didn’t want her personality showing through.

She was feeling a bit nervous and shy, so I asked if she’d like to role-play the first part. She said yes, so I pretended to be a doctor making a housecall. I asked if she had a tummy ache, and she said yes. Felt her forehead, and said I should get a temperature as well. As I helped her get undressed from the waist down (she was shy about taking her top off), the nervousness started to go away. I had her lie on her tummy and inserted the thermometer gently into her bottom. This felt nice to her, and I asked if she’d like to liven things up a bit. She said sure, so I inserted a couple of glycerin suppositories. That kept her amused while I filled the rectal squeeze bulb with mineral oil.

She’d told me that she had a longstanding fantasy about being done across someone’s lap with a squeeze-bulb. Still role-playing a bit (as we got more excited, the role-playing went away), I said that she seemed a bit impacted, so I’d give her a mineral oil enema to soften and lubricate her. I put a pillow across my lap and she lay down. I could feel her breathing getting heavier. When she was comfy, I inserted the nozzle of the bulb. I asked if she was ready, and being told that she was, I began to slowly squeeze the heavy oil into her. She shivered a bit, as the cool oil filled her. I slowly withdrew the nozzle, and then gently slid a finger in, to “help her hold it while it worked”. By this time, she was relaxed and getting into it – I explored her pussy and clit with a couple more fingers. She began to respond and encourage me, and we got her up to a rather nice orgasm.

As she was expelling that, I filled the motel ice bucket with hot water, and soaped it. We joked about the fit the motel staff would have if they knew what we were doing with it. Her shyness had gone away – I was using the sink right next to the potty. Asked her to feel the water for temperature, and she did and pronounced it right. Showed her the milkiness of the solution, and she suggested a bit more soap, which I added. We went back to the bed, and I put the pillow on my lap again. She got back across my knees, and I slowly and gently gave her about a quart, one bulb at a time, asking each time if she’d like more. Then, I slid the vibrator in her pussy, while fingering her anus. She started breathing harder, and I followed her cues to tickle her clit until she came. I noticed that she doesn’t have any problem retaining while she’s aroused, and we laughingly decided that the butt plug wasn’t needed. She also said she didn’t particularly feel interested in the 8” dildo nozzle.

I asked if she’d ever tried a glycerin enema. She hadn’t, but was interested. I switched to the douche bulb with 4 oz of glycerin and 8 oz of water. This time, she wanted it in the knee-chest position, bottoms up with head on the pillow. When the solution was in, I slid the vibrator in front and candymaking thermometer in the back. We both noted with interest that with the vibrator and thermometer at the right angle, we could both feel the thermometer vibrating. She almost came, but the glycerin wanted out, and we decided that discretion was the better part of valor.

We discussed what she’d like to do next. Since time pressed, we decided not to try the double-barreled enema and douche, and went with 2 quarts of hot water with baking soda, from a bag with douche nozzle. She preferred knee chest to start, then as the bag drained she started to cramp a bit. We switched to Sims (left side, knees up) to finish. Since she was holding nicely and aroused again, I slid the long vibrator in front, short one in back, and proceeded to amuse her mightily with the resulting sensations. We’d both agreed to keep this on an enema and masturbation footing, which is why she’d left her top on. By this time, she was aroused enough that when I tentatively stroked her breast, she encouraged me. This time, she didn’t need to go after the first orgasm – I asked if she’d like to go for another, and she enthusiastically agreed. This one came quite a bit quicker – when her clit wakes up, she’s quite the bouncy babe. Good thing, too – the enema started knocking on the door to get out. I had to help her up, though – her knees were shaking, and we laughed about it…

I never want to send a lady away sore, so I always add an after- treatment of Prep H suppositories and ointment. I also, incidentally, insert prep H suppositories between enemas. This is both to soothe and lubricate, and because I like the excuse to slide my finger into a quivering bottom. She wanted this on her back, with legs up. I’m probably the only guy around who can make a 3-ring production out of inserting a suppository – she found it most entertaining. I teased her anus with the tip, then slowly inserted it about a quarter of the way. Let her anus squeeze it back out a bit, then pushed in – giving her bottom sort of a mini-fuck. Then, I pushed it in far enough that the tip of my finger was against her anus, and let it melt a bit. Finally, I buried the now rather squishy suppository to the depth of my finger. Asking if she was ready for the second, I got a somewhat shaky yes. She seemed to be having a bit of trouble breathing slowly… I slid the second in with a bit less fanfare, then reached for the prep H ointment tube. I lubricated the nozzle with a squirt of ointment, then slid it in. She enjoyed the flow of the lubricating grease, and said it felt nice and cool. I withdrew the nozzle, and contemplated her anus.

Usually this is the point at which I pat the lady’s bottom and clean up the equipment while she dresses. This time, I slowly slid a finger into her anus, and began moving it around. Feeling her pussy get moist, I inserted a finger in there. Earlier, she’d been a bit tight in the back – now she was totally open to me. She started rubbing her clitoris while I gave her a thorough rectal massage, stirring the ointment and the melting suppositories around. I massaged her breasts with my other hand, and we went on to give her a final orgasm.

She’d almost changed her mind while waiting for me that afternoon – nervousness, what am I doing here, this is crazy, all those thoughts . As she was dressing, she said she had no regrets whatsoever about meeting me, and wanted to do it again – she hadn’t come that much or that hard in years. This, of course, made my day – I get off on the pleasure ladies take in my treatments.