When Ruth, a friend of the family and a psychiatrist, offers to try hypnosis to help with young Jordan’s fear of flying they figure it’s worth a try. After the first session, Jordan’s not convinced that it was just his mind she’d been tinkering with.

I guess I was a fairly typical sixteen-year-old boy in that my two favorite hobbies were masturbation and ogling members of the opposite sex.

Being an only child the female that featured regularly in both cases was my mother. I watched a lot of internet porn to fuel my first hobby and my mom very much fell into the category of MILF.

She was a magnificent woman, five feet ten inches tall, with D-cup breasts that appeared to be unnaturally firm but which, to the best of my knowledge anyway, were quite real. She had a spectacular hourglass figure and an ass that I would happily have lost a limb or two to see in the flesh.

Unfortunately for me, Mom didn’t generally dress provocatively around the house so I had to satisfy myself with the occasional flash of leg or cleavage, or on two occasions that were imprinted forever on my memory, a glimpse of her panties.

One time that she did dress up was when she went out on one of her girl’s nights out. They all made the effort to look nice and she would often wear outfits that fueled several happy wanking sessions for me. A particular favorite was a white miniskirt that, although not super short, clung to her ass like a second skin. From the total lack of VPL, I knew that she either wore a tiny white thong with it or, just possibly, nothing at all.

Depending on who was the designated driver sometimes Ruth would pick her up. She’d been a friend of my mom’s almost since we first moved into the area three years ago.

Ruth was very nearly as hot as Mom, slightly shorter and with smaller boobs but she also had an ass that was to die for. She was always very friendly towards me when we met and sometimes even a little flirty. One day, as they were leaving, she patted me on the ass. I say patted, actually, it saw more of a stroke. Anyway I thought it was pretty cool of her, and it gave me a nice little chubby.

My parents wanted to go on a holiday to Europe but I was being a problem about it. The only flight I’d ever made was an internal one and it completely freaked me out. I was OK until I visualized the huge drop under the plane, all the way down to the ground, after which I couldn’t get the image out of my mind. I spent the rest of the flight with my hands wrapped around the armrests like claws, shaking violently and in a state of complete panic.

Ruth was a psychiatrist and when Mom mentioned my issue to her she suggested hypnosis. She admitted it had fallen out of fashion somewhat in psychiatric circles but said she’d had some success with it with other phobias. They agreed it was worth a try and Mom made me an an appointment to see her the following Monday after school.

Her office wasn’t too far away so I cycled there and went in. Her receptionist was putting on her coat as I arrived but buzzed Ruth and then told me to go in.

“Hi Jordan,” she said. “take a seat on the couch.” I was a bit surprised, I thought psychiatrist’s couches were only in the movies. She sat in a chair facing me, put a pad on her lap, and crossed her legs. I got a brief flash of her red panties, which was really nice.

“I’m sure your mom told you but I’m going to be hypnotizing you today to see if we can alleviate some of the anxiety you feel about flying.” She then re-crossed her legs giving me an even nicer view. I was starting to get a bit of an erection, as I said earlier she’s pretty hot.

She uncrossed her legs and leaned forward. I could clearly see the crotch of her red lacy panties and I was really quite hard now.

“You need to be completely relaxed for this to work. You look a bit stressed to me. Are you OK?” I was before you kept showing me your pussy, I thought, but kept that to myself obviously.

“I guess I’m a bit ... nervous,” I said, a bit erect is what I thought though. She went to a cupboard and got a bottle of pills out of it. On her way back she poured a glass of water and brought them over to me.

“This will just help you to relax,” she said and handed me a small green capsule and the glass. I figured that she knew best, so I put the pill in my mouth and washed it down with the water.

“I’ll just give it time to take effect, you might like to lie down,” she said. “I’ll be back in a few minutes.” And she left the room.

I lay down on the couch and the next thing I knew she was shaking my arm gently and calling my name.

“Jordan, come on sleepy head,” she said to me. “You dropped off completely there at the end. How are you feeling?”

“OK, I guess,” I told her. “very relaxed at any rate. Did you hypnotize me?” I asked her, I didn’t remember anything at all.

“Oh yes,” she said. “you seemed to take my suggestions on board but it’ll take a few more sessions to tell how well it’s working. I’ll make another appointment for you with your mom.

She ushered me out of the door.

“Give my best to your Mom,” she said, just as I was leaving.

I felt a bit dazed and, as I walked away, I had to adjust my junk which felt a bit uncomfortable. I didn’t think anything more about that until I got home and went for a pee.

A bit of back story is required at this point: When I was about twelve or so my mom used to get on my back all the time about fiddling with my bits, telling me to leave it alone. In the end, she must have had a word with Dad because he sat me down one day for a chat.

He started by telling me that Mom didn’t understand about men and their peckers, how sometimes it just feels wrong and needs to be ... adjusted. I nodded to him, finally someone who understood. He then gave me some advice.

“If you put some talc down the front of your underwear it helps to stop things binding and...” he confided quietly, “it feels better too. Don’t go mad, and make sure you use unscented talc. You don’t want to smell like your grandmother.”

I tried it and he was right. I thought that I understood what he meant by feels better as well. When I stroked it my hand slid over it really nicely. That was the first inkling I’d had that my Dad played with himself too, and I was surprised, to say the least, and a bit grossed out, to be honest.

I followed his advice from then on and it must have worked because I don’t remember my mom getting on my case again after that.

What I noticed when I went for that pee was that there was no talc on my penis; it was actually a bit sticky. I could think of only one explanation: Ruth had done something to it while I was under. I didn’t think it would go down well if I accused Mom’s best friend with no real proof so I kept quiet.

I thought about it, off and on, until the day before my next appointment when I decided that I’d try to find out what she was up to.

Again I was her last patient of the day and it went pretty much like the first time.

“I think I’d better give you the relaxant again, just to be sure.” she said and offered me another capsule. I palmed it, as I’d practiced at home a few times. and pretended to take it. When she took the glass away I slipped it into my pocket then I leaned back and shut my eyes.

“I’ll give you a few minutes,” she told me and left the room. I got up and had a look at the bottle she’d gotten the pill from. The label said Sonata(Zaleplon). I quickly Googled it and found out it was a sedative used to treat insomnia, not exactly a relaxant!

She came back about twenty minutes later and I pretended to be asleep.

“Jordan,” she said softly, and when I didn’t respond I felt her poke my arm, gently at first, and then quite hard. The next thing I felt was her hands on my shorts, opening the button, and then pulling down the zipper.

It was really difficult at this point not to allow my breathing to give away that I wasn’t really asleep, but I did my best. Then she pushed my shorts down as much as they would go and did the same to my briefs. When I felt the cool air on my dick I knew I was right and tried to keep calm, as I waited for what I desperately hoped was about to happen: my first-ever blowjob!

My prayers were answered when I felt a warm wetness envelop my cock and her tongue start licking around my knob. It was the most amazing sensation I’d ever felt, and in no time I was fully erect.

As there was no chance of her looking up from that position I risked opening my eyes and the sight of her head bobbing up and down on me was incredible, like something out of one of my most lurid fantasies.

She wrapped one hand around my shaft and wanked me while the other played with my balls. She was humming happily while her lips and tongue danced over my knob. I was close to cumming but I wanted evidence, so I took my phone out of my shirt pocket. I wasn’t going to risk fucking this up so I waited until I started to cum into her mouth before holding my phone so that I’d get a good shot of her face and my dick.

She was still making happy noises as she sucked every last drop of spunk from me and it was utterly, utterly gorgeous. I was shaking like mad so I just kept pushing the shutter button and hoped that I’d get some good ones.

While she was licking my softening cock I risked a quick look at the pictures and some of them were great.

I stroked her hair gratefully and felt her freeze.

“That was lovely Ruth,” I said quietly. “but I’m guessing that wasn’t part of my treatment.” When she looked up at me her expression was a mixture of horror and guilt.

“I’m so sorry Jordan,” she whined. “I shouldn’t have done that. I’ve never done it before, please don’t tell anyone.” I didn’t believe a word of it.

“You mean you’ve never been caught before.” I challenged her, and now she just looked guilty as hell.

“But please don’t tell. I’ll do anything, anything at all.” I really liked the sound of that. I wasn’t sure what I wanted to do and I didn’t have time right now; the last thing I wanted was for Mom to get upset at me being late home for dinner.

“We’ll see,” I said, tucking my dick away and getting up. “I guess it depends on how nice you are to me...” I thought I’d test how far she’d go, and I put my hand up her skirt and cupped her panty-covered pussy.

I was watching her face as I did it, and she looked surprised at first and then just sort of resigned.

Even through her panties, I could feel how hot and moist it was. I snuck my hand in the side of her panties and let my fingers explore. I’d never touched a girl down there before and it was really interesting. What I didn’t like was all the hair; none of the girls in porn had any hair.

“I don’t like this,” I told her tugging on her pubes. “I want this gone when I come next time.” She sighed and nodded. Encouraged by her apparent capitulation I pushed things a bit further. “And don’t bother wearing panties either,” I added. I found the idea of her spending the day with a bare pussy, waiting for me, very exciting.

By this time my questing fingers had found a lovely wet hole down there and I pushed my finger inside. She actually seemed to like that and pushed herself against my finger.

I looked at her clock and cursed. It was getting late. I really didn’t need Mom getting cross with Ruth and maybe not letting me see her again.

“Make another appointment with Mom,” I told her. “and make it soon.” I removed my hand from up her skirt and grinned at her before I left. She didn’t smile back.

As I walked over to my bike I sniffed at my fingers. At first, I wasn’t sure, but the more I sniffed the more I liked it. In the end, I licked a finger and I liked that even more. So now I knew what pussy tasted like, and I thought maybe I’d like to lick it straight from Ruth’s cunt on my next visit.

Once again my appointment was the last of the day so there was nobody there but Ruth and me. She stood up as I entered her office and I thought, why not, and went over to her and gave her a hug. I put both hands on her ass and gave it a nice squeeze and then pulled her skirt up so that I could see if she’d followed my instructions.

I was delighted to find that she had, and I ran my hands over the bare cheeks of her ass. God knows how many times I’d beaten off dreaming of the moment I finally got my hands on a gorgeous, naked female ass and it didn’t disappoint, it was so firm and smooth and soft and lovely. The cheeks fitted into my hands perfectly and I pulled her hard against me so that she could feel my hard cock pressing into her.

I finally let her go.

“I’d like you to take everything off now please Ruth,” I told her.

“Please Jordan, don’t make me do this, I beg you.”

“I guess you should have thought of that first shouldn’t you?” I said, blatantly looking her body up and down and licking my lips in anticipation.

She slowly undressed until she was down to just her bra and skirt. She gave me one last pleading look and I just nodded and smiled. She unclasped the bra and let it fall but managed to keep her hands covering her breasts while she did.

“All of it,” I said, but softly; I was sure I’d won now.

I smiled when I saw her bald pussy. She tried to cover herself with her hands again but I touched her arms and she dropped them to her sides.

I walked around her, drinking in the beauty of her naked body. I could see that she was trembling but I didn’t know if she was cold or frightened or maybe even excited.

I loved all of her: the gorgeous heavy breasts, the soft-looking pussy, but most of all I loved her ass. The peach-like shape spoke directly to something deep inside me.

The sense of power that I felt knowing that this intelligent, beautiful woman would do anything that I, a mere schoolboy, wanted was intoxicating.

Eventually, I touched her breasts. I watched, fascinated, as the area around her nipple shrank and wrinkled at my touch and the nipples themselves hardened and grew. I saw goosebumps rise on her flesh and her trembling got stronger. I smiled, it had been excitement.

She was standing with her legs close together and I put my foot between hers and nudged her legs apart. Now I had access to that lovely pussy and I stroked it gently reveling in its softness. I ran my finger along her slit until I felt the wetness again and smeared it up and down making her slick with it.

Standing at her side I was able to fondle her luscious ass with one hand and her pussy with the other. I was in absolute heaven. There was only one thing that could make it better. I took her hand and placed it over my hard cock. Without prompting she squeezed it and then took it out.