Jessie - An Imaginative Girlfriend

Chapter 1

Jessie and I do not have a very conventional relationship but what we have suits us both. She is both bisexual and dominant whilst I am a submissive straight male. Whilst Jessie brings women home to our bed and I am sometimes allowed to watch, I am not allowed the same privilege and she has made it very clear to me what will happen to me if she ever thinks I might stray.

We met on an online dating site where she made her nature and what kind of man she was looking for very clear. I was intrigued and replied to her advertisement. Although I am in a position of authority in my professional life I have always sought sexual relationships with dominant women who could be persuaded to punish me.

My fetish is not a particularly complicated one. I don't need any role play or fancy dress, but I do need the occasional severe thrashing with a cane across my bared buttocks. It needs to be painful enough that it cannot be born without my being bound over a table, bed, or punishment trestle. And it must leave marks. Long red parallel stripes that take weeks to heal.

I cannot explain this need. It probably has its origins from canings I received when I was younger, but its origins are unimportant. It is the way I am, and it is in my nature

I am aware that there are people who believe that anybody who can seriously punish someone they love must have a psychological problem, but I believe this is untrue. It is my experience that people like this are difficult to find.

And up until I found Jessie this was certainly the case. I had a couple of girlfriends who were happy enough to spank me as part of our lovemaking and another who caned me in anger after I got badly drunk one night, but she didn't want to have sex afterwards because she was still angry.

In the end I started to see Mistress Anne. She is a professional dominatrix and administers severe CP to those who want it. Despite this she did not fully solve my need. How do you go home to a vanilla partner with a swollen ridged backside and make love soon after you have been caned? Neither had I ever considered using the services of a hooker.

After I replied to Jessie's advertisement she suggested we exchange photographs and if we were both amenable we could meet. The image that she returned to me revealed a black-haired women with piercing ice blue eyes, and high cheek bones. She looked to be about thirty years old.

I waited a few hours before suggesting we meet. I didn't want to make it obvious how keen I was for this to happen. Jessie lived In Liverpool whilst at the time I lived in Manchester, so we agreed to meet halfway in a pub in Warrington the following Saturday night.

On the Saturday evening half an hour before we arranged to meet I was sat in the pub nursing a pint of bitter. My back was against the wall from where I could watch the door to the bar. The allotted time passed, and I was just starting to wonder if I was about to be stood up when the door opened, and she appeared. She was immediately recognisable from her photograph. She was of medium height and build; not overweight but not exactly thin. I was pleased by her looks.

She closed the door, stood still, and looked around the room and then her eyes alighted on mine, and she smiled briefly and crossed the room to the table where I was sitting.

"Hello, I'm James," I said stiffly

"Pleased to meet you. I'm Jessie... Jess for short if you prefer."

"Would you like a drink?" I asked.

"I'd love a G and T. I'm parched."

As I stood waiting my turn to be served I could see Jessie watching me in the mirror placed on the wall behind the bar and I hoped she liked what she saw. I haven't changed much in the two years since we met, and I am 35 years old, six feet two inches tall, with a slim athletic build, and blond hair. I'm told I'm good looking, but beauty is in the eye of the beholder.

That evening went well, It turned out we had both travelled by public transport, Jessie by train and I by bus, so we were able to have a few drinks. We talked about ourselves, or jobs, and our backgrounds but no mention was made of our kinks. By the end of the night, I believed this was a potential relationship worth pursuing and she must have thought so too because she agreed to meet the following Friday evening at an Indian restaurant in Warrington.

The following Friday night I drove over to Warrington. Again, the evening went well, and we had a couple of glasses of white wine each with the meal. After we finished, being the gentleman I am, I offered to drive her home. When we got to the street where she lived I parked the car and walked her to her front door. Suddenly she turned stood on tip toes and kissed me hard on the lips, Then she turned,unlocked the door, and invited me inside.

Chapter 2

The inside of the end terraced house had been completely gutted and redecorated. The lounge-dining room was brightly lit and furnished in a contemporary fashion. Sitting on the sofa was a striking blond woman. As I briefly appraised her I must have shown my admiration because as Jessie introduced me to her flatmate Sarah, I saw a momentary flash of anger in her eyes.

Jessie made coffee for us whilst Sarah excused herself and went to her room. A little while later Jessie stood up and addressed me.

"You must know I like you. Come on."

And she took me upstairs to her bedroom. She opened the door and beckoned me to go in then followed me in before shutting and locking the door behind her. She turned and once again kissed me, only this time a little longer than she had at the front door. Then she disengaged and as we sat together on the bed she spoke to me in a serious tone I had not heard before.

"If we are going to be good friends you need to understand the rules. First and foremost is I am to be the only woman in your life. Don't ever again admire another woman in my presence and never ever be unfaithful to me. If you eye up another woman and I see it you will be severely caned. If you are unfaithful I will finish with you."

"I am bisexual, and Sarah is my lover." She knows I will fuck you and she is good with that. I am faithful to her with regards to other women and will continue to be. And I will not look at another man as long as I am with you"

We are going to start as we mean to go on and your "Hots for Sarah" have already earnt you a sound caning. To do that effectively I need the dining room table and the privacy to do it. Sarah works tomorrow from 8 o'clock and doesn't come back until early evening so you can look forward to eighteen on the bare late tomorrow morning.

Tonight, I'm going to give you a taster just to let you know what you have signed up to and make sure you can take a sound caning. Now take off your sock's, trousers, and underpants. Face the bed with your legs a little apart and the bend over and place the palms of each hand firmly on the bed. Do not get up during the punishment but only when I tell you to. If at any stage you wish me to stop say so and I will unlock the door and you can go. I like you, but if you go you will not see me again.

I did as I was told and soon afterwards was bent over the bed as instructed. I felt Jessie pull up my shirt tails to fully expose my bum cheeks. She crossed to the cupboard in the corner and took out a thin rattan punishment cane about a yard long. "This should do nicely for now, "She murmured as she swished it through the air of couple of times.

I felt her tap it across my bum a couple of times and then there was brief pause before the cane whistled and cracked and is usual on the first stroke the impact was felt a second before the searing pain. I gritted my teeth and after a maybe ten second pause heard the whistle and crack for the second time. This time the pain was slightly lower yet just as bad and I pushed my palms down firmly but couldn't prevent my arse from wriggling. The third and fourth strokes followed rapidly afterwards, but she waited a good 20 seconds before applying the fifth. This stroke was the worst so far and was placed over the centre of both cheeks and I hopped and wriggled for a few seconds after she had struck but managed not to get up. Thus far the discipline had been conducted in silence. I was determined not to give Jessie the satisfaction of making me cry out and she in turn had said nothing. Then she broke her silence.

"Now this IS going to hurt."

And then she delivered the last stroke. It was much harder as evidenced by the far louder whistle and crack on impact and she had brought the cane down into the exquisitely tender sweet spot between the top of my legs and my bum cheeks. It was agonizing and this time I gasped but I still managed to keep position.

"Get up."

"You'll do."

"Now take your shirt off and lie on the bed."

I lay on the bed with my head on the pillow as Jessie unashamedly slipped her dress over her head, unclipped her bra, and stepped out of her panties. She was more sexy than I had imagined with a narrow waist, broad hips, and a large round ass. He breasts whilst not large were round and firm and her nipples were clearly erect.

She climbed onto the bed and knelt astride me offering her sex to me. I used my tongue to find her clitoris and slowly and deliberately I licked it until it was hard, erect, and engorged. At first she took her pleasure in silence but soon she started to moan softly and reached forward and took my foreskin between her thumb and two fingers and very slowly and gently slid it up and down over the tip of my erect penis. As I continued to tongue her, her moans grew louder, but she maintained her slow exquisite stroking of my penile head. Soon I felt her thigh muscles start to tighten and relax and then she came to a long shuddering climax and as she firmly held my penis cried aloud, "Ohhhhh Yes!"

She lay next to me and as she continued to wank me I found her clitoris again and started to slowly rub her in small circles with the flat of two fingers and she very softly started to moan again. This time her orgasm was taken with a long drawn out silent as her deep blue eyes looked into mine wide with longing.

When she had recovered I knelt between her widely spread legs and slowly penetrated her well lubricated vagina. To begin with I delivered long hard slow strokes but as her passion grew she loudly pleaded for me to go faster, and I felt her knuckles on my pubis as she desperately fingered her clitoris.

"Give it to me. Oh, please give it to me. I want it so bad."

"Fuck me hard. Fuck me hard."

"I'm going to come. I'm going to come."

"Ohhhhhhhh!"

And as she came her vaginal muscles spasmed, contracted, and relaxed; and this with her loud sounds of ecstasy drove me over the edge, and I came long and hard deep inside of her.

We lay in bed together quietly as we recovered, and our breathing returned to normal.

Jessie spoke, "Now that was good sex. Best I can remember with a man."

And then she put her head on my chest and as I held her in my arms she fell asleep.

Chapter 3

I awoke to the early morning sun and found myself alone in bed. As I orientated myself in a strange place I thought back to the events of the night before which were made even more real by my bruised backside. I realised that in a little while I was likely to experience far worse and my dick stood rock hard again at the thought.

Just then jessie entered the room. She was already fully dressed and had made herself up and looked beautiful.

"Good morning. Hope you slept well. I'm an early riser so I let you sleep in. It's 9 o'clock and Sarah's gone. If you want a shower and a shave you'll find a spare toothbrush and some disposable razors in the bathroom. There's a robe you can put on afterwards. It may be a little short but otherwise it should fit OK. No point in dressing quite yet. We still have unfinished business."

She left the room and I heard her go downstairs and I took her advice and had a shower, washed my hair, shaved, then brushed my teeth.

Jessie was in the kitchen at the back of the house, and I had to pass through the lounge-dining room to get there. As I passed the table I noticed a pillow, some leather straps and ropes, and a selection of canes ominously resting on top. I knew then that Jessie had been serious about what she had promised me the previous evening.

For now, she was behaving as if nothing was planned. I sat down at the table where she had prepared toast and eggs with coffee, and she leant over and kissed me. She smiled at me.

"I still feel slept with. Thank you."

And we sat at the table and talked as if we had known each other for months or years. Thinking about it of course, we knew things about each other that our closest friends knew little or nothing about.

A little later I found myself bound firmly to the table as I lay over the pillow. I wore soft leather wrist and ankle straps with metal rings and Jessie had attached these with ropes to the tops of the legs in front of me and the bottom of the table lags. I was naked and my already well marked bum cheeks lay waiting and I trembled with a mixture of fear and need.

I heard her speak softly and calmly.

"You are not going to enjoy the next 5 minutes. Buts it's what you wanted and need, and I am very happy to be the one to give it to you."

"Prepare yourself."

And Jessie then proceeded to give me the worst and best punishment of my life. Every stroke was delivered full force and as hard as she could deliver at regular twenty second intervals. This gave me plenty of time to assimilate the awful pain each time the cane bit and to anticipate the next stroke and when she had finished I had finally broken my silence and howled for the last six strokes. My buttocks were a swollen tapestry of red and blue parallel stripes with the imprint of the cane tip clearly visible. It was a testament to her skill that there was little overlapping and only a little bleeding.

She unbound me but left me to recover over the table and then a few minutes later returned and started to gently rub salving ointment into my welts.

Then she led me upstairs to bed where I lay on my stomach. A moment later I felt her warm naked body next to me and she stroked my hair and whispered how brave I was. She asked me to watch her and as I gazed across at her as she lay with her knees flexed and her legs apart she started to finger her pussy. That was the sexiest and most intimate moment I believe that I have ever shared with another human being. I looked deep into her beautiful blue eyes as she touched herself and watched her pleasure grow and grow until with her mouth open and a deep sigh she climaxed.

Chapter 4

We woke several hours later, and we lay in each other's arms and kissed.

"I didn't think" she said

"Can you drive home? Don't worry I can drive your car."

"I'm going to take you home and stay until Monday morning, catch the train back, and go to work. I'll put some things in a bag and leave a note for Sarah"

She drove me home, stopping only to buy a couple of large fillet steaks, two of bottles of good red wine, and a few other groceries.

On the way Jessie opened up to me. She had mentioned that she had been brought up in South Africa but what she hadn't said was that she had an abusive father who had caned her on several occasions, most notably when her mother had caught her masturbating. She wondered if this drove her need to punish men and her bi-sexuality.

My answer was that I was no psychologist but that we must live with who we are and not spend too much time looking for reasons for our traits or feeling guilty about them.

The rest of that weekend was wonderful. With the help of some painkillers, by Sunday morning I was able to forget my swollen backside and arm in arm we walked in the park. We went for a light pub lunch and then spent the afternoon in bed.

This time she knelt astride my legs and inserted a long penis shaped vibrator with a clitoral stimulator into her vagina and as it hummed inside her and against her clitoris she took the helmet of my dick in her mouth and moved her tongue in circles around its rim before grasping the shaft with only two fingers and slowly wanked me into her mouth. She looked down at me in triumph and as my seed dribbled from the corner of her open mouth I reached up and held her breasts and watched her as she moaned, and then shuddered before collapsing across my chest.

In the evening Jessie cooked the steaks which we ate with sauteed potatoes and asparagus, and we drank the wine and talked some more. And finally, she told me about her relationship with Sarah. I had not wanted to ask for fear of annoying Jessie, but she was very open. They were flat mates, and they were both bisexual. They hadn't known about each other's sexuality when they moved in together but had got drunk one evening "And it just happened." Sarah had a boyfriend she saw most weekends and jessie told me that Sarah hadn't told him of her relationship with Jessie. Jessie thought this was dishonest but said that was it was none of her business. Jessie and Sarah rarely went out together but fucked twice or three times a week when they felt like it, provided they didn't have some other commitment.

"I want to continue to see you and there will be plenty of time for us. I've told you the rules and you know what to expect if you break them. You can expect to be caned again, but not soon, and only when you deserve it. When I do discipline you It will be done thoroughly, and you will be told in advance so that it can be done early Friday evening to give you the weekend to recover."

That evening we sat together watched some television and then later in bed she fell asleep in my arms.

In the morning she crept out before I awoke but left a large sheet of paper with a note scrawled in block capitals with red lipstick." REALLY ENJOYED MYSELF. RING ME TONIGHT JESS XXX."

Chapter 5

That was how our relationship started sometime around two years ago. I'm not great with dates. Sarah moved out of the flat over a year ago and Jessie asked me to move in with the understanding that there might be occasions when a women might share our bed. On occasion I have been allowed to watch if her partner for the night is comfortable with this arrangement. Jessie does not have a regular girlfriend. She has told me that she can't have two relationships at the same time even if they are with people of different sexes and she now loves me. And she wasn't in a relationship with Sarah who was a "Fuck buddy."

A few months before Sarah moved out to take Job abroad and their "Arrangement" ended Jessie told me to come over to stay at the flat for the weekend and promised me a treat, I must admit I arrived at her flat with some trepidation and unclear as to what she might have planned.

It was a warm summers day and I arrived about seven in the evening and rang the bell. There was no reply, so I let myself in with my key and decided to wait for Jessie to come back from wherever she had gone. Just then I heard her call.

"Come up. I'm in my room."

I dropped my overnight bag, trotted upstairs, pushed open the door to Jessies room and went in. And my jaw dropped. Jessie and Sarah were in bed covered by a single sheet.

I just stood there with my mouth open.

"I told you he'd, be surprised," said Sarah.

"Would you like to watch," asked Jessie?

"Don't worry I don't plan to punish you if you say yes."

And I nodded.

"Fine and feel free to touch yourself if you want. No penalties."

And with that Jessie threw the sheet onto the floor. Sarah was a big titted leggy blonde with a small tight arse. She lay back and spread her legs exposing her smooth shaved cunt whilst Jessie lay full length on her belly and with her head between Sarah's thighs started to lick her. Sarah groaned and with her arms against her sides grasped the sheets she was lying on and simultaneously pushed her sex towards Jessies busy tongue.