Teaching Jenny to be more adventurous

This is a true story and happened recently I have changed the lady's name to protect her. 

Several years ago I worked with a young lady (27) called Jenny, she was tall, slim, had a great body and fantastic personality. We got on really well and I even attended her wedding (invited by both her and her partner), it was like I was her Dad at work we talked about just about everything. We attended several work 'does' and nights out, her favourite dressing style was Goth.

Friday Night.

I retired late last year and hadn't seen her for sometime but last Friday I went into the local town for a drink and bumped into her, she was as usual dressed Goth style, her trousers were so tight, I jokingly told her that I wished that I had been the person using the spray gun she gave me a strange look, realised then that I was teasing her and gave me a friendly punch and asked me if I wanted to tag along with her and her friends. I declined saying I was far too old to stay the course, her friends then started to cajole me to join them. Eventually I said I would for a bit but would disappear when I had, had enough.

About two hours later I saw Jenny waving me urgently, I crossed to where she stood and when I reached her she told me, blushingly, that she had just proved that her trousers had not been sprayed on as she had just split them at the back and asked me to help her to get to the ladies by walking close behind her, I put my arm around her from behind and as we walked across to the loos I asked her how her husband was and was shocked to be told they had split up because he was cheating on her.

She came out of the loo cursing saying she would have to go home and change, I told her to wait for a few minutes while got my jacket and I would walk her out, as I got back I offered her my jacket which would cover her back as I helped her into it, I looked down and saw what appeared to be a knickerless, nice area of an extremely tight butt displayed (sadly too quickly hidden).

We got to her house and she asked me in, poured use both a drink, giving me my coat she walked to the door saying she was going to get changed. I tried hard not to look as her rear end played peep-po through the split, as she got to the door she said did you enjoy the view. I was embarrassed to be caught looking and blushed but taking the bull by the horns laughingly said "yes, but it was over far too quickly".

Jenny laughed, walked back towards me, turned and slowly walked back to the door, said was that better, laughed and went to get changed, she came down wrapped in a loose dressing gown, picked up her drink took a long swig, sat next to me and burst into tears.

I sat and let her cry for a few minutes feeling awkward, then put my arm around her pulled her into me and just held her. When she finished I poured us both another drink, sat, pulled her back into me and asked what happened and she told me all about the break up. It seems that he had had a string of affairs, finally Jenny had enough and kicked him out and he told her that she was not 'adventurous enough' for him.

I was truly astounded and didn't know what to say or do, so I just sat there holding her. Eventually she asked me what I thought he had meant, I thought for a few minutes then asked what type of thing he had asked her to do, she went quiet, then turned bright red and said he had asked her to do lots of different things like taking him in her butt and things like that, then asked me if that was natural. I explained that some people liked it but it was a personal thing and not something anyone should be forced into, she asked me if I had ever tried it, I said only with a lady that enjoyed it and that she had asked me to do it.

Jenny sat forward, took a long swig of her drink, looked at me and asked if I would "help her to become more adventurous". 

To say I was shocked was an understatement, I tried to explain that I was honoured to be asked, but as I was over twice her age and that there were lot of guys her age that would be far better it wouldn't be right, she just said the difference is that I trust you. 

She turned back into my arms and slipped onto my lap, I just held her for a while, feeling very unsure of what was expected of me, slowly I started to caress her head and hair, she snuggled in deeper. I kissed the top of her head, she looked up so I kissed her on the lips, she opened her mouth to allow me use my tongue which she reciprocated. 

Jenny lifted her arm to put it round my neck and as she did so the dressing gown gaped open slightly so I tentatively ran my hand down her side and started to undo the belt, Jenny stiffened slightly so I stopped and asked he if she wanted to stop and that I would understand, Jenny looked at me and said "if you stop now you won't make it to the door alive". I carried on undoing the belt.

As her gown became looser I could see she was wearing a small white lacy bra which left some to the imagination making it even sexier, slowly I slipped the gown off of her shoulders and began kissing her neck with little nibbles and gentle bites, I slipped the right strap from her shoulder, she leaned back giving me better access. I undid the bra and lifted it off exposing a fantastic pair of boobs with nipples that stood so proud I was stunned, they must have been at least half an inch plus. Gently I ran a thumb over one while sucking the other in to my mouth, Jenny shouldered and had her first orgasm of the night.

I moved round so that Jenny was lying on the sofa and I was then kneeling at her side, moving the gown aside completely, leaving her in just her knickers that were a match the bra. I asked her if she was still sure about what she wanted and looking straight into my eyes she nodded her answer. 

I started to suckle and play with her nipples - slowly kissing down towards her navel, I moved my hand between her legs and caressed her mound, as I started to ease her knickers down she lifted her hips to help, I took them off and gazed on a one of the nicest bodies I have seen in many years, her pubic hair was trimmed short and in to what I believe is known as a landing strip.

As I knelt looking, thinking there surely must be a guardian looking over me, Jenny asked me what I thought and I answered simply with the word "Stunning" and I loved what I was seeing.

Jenny sat up and started to undo my shirt and kissing my chest, this might sound sexist but, at first I was very uncomfortable with this, I'm 65 and not in the best shape, although 6 foot tall I have a slight pot belly and I have let myself go a bit, but bless her, Jenny took not a blind bit of notice, stripping me down to just my boxers, now I don't consider myself big but at around 7.5 inches I do believe I'm a good average and as I stood there I was as hard as I have ever been.

Jenny knelt in front of me and slowly slid my shorts down lifted her hand to cup my balls, took the tip of my penis in her mouth, oh jezz the sensation was total magic. I lasted about 2 minutes before I had to stop her, I explained that it had been a long time since I had been with a lady and if she continued I would not last long enough and I wanted so much to pleasure her in the fullest.

I got Jenny to sit on the sofa again, knelt in front of her, slid her hips to the edge, opened her legs, then lowered my mouth to heaven.

I took a long slow breath through my nose, Jenny's woman aroma was sweet and beautiful, I slid my tongue into nectar, gently licking and sucking, tonguing both clitoris and pussy, I felt Jenny's legs start to tremble, suddenly she grabbed me, pulled me up saying fuck me, for gods sake fuck me. She pulled her hips forward and I slid straight into her. Wet, smooth, tight. I pushed in deep and hard, slowly pulled out and hard back in again several times, Jenny's whole body went stiff with the start of an orgasm. I put my thumb on her clitoris and rubbed while still pushing in hard, Jenny's orgasm was massive, I managed to hold back (how I will never know) and came just as she started to come down which thankfully brought her back to another smaller orgasm.

I leaned forward, slipped my arms around her and we stayed like that for about 5 minutes until I went totally soft and slipped out of her. I kissed and thanked her for the honour and pleasure she had given me.

Jenny stood up took my hand and led me upstairs and to bed, she cuddled up to me, kissed my chest and promptly fell asleep wrapped in my arms.

Saturday Morning.

I woke about 5am, Jenny was still curled up next to me her head nestled on my shoulder and her one leg over mine, my left hand rested in the small of her back, I lay there wondering at my great fortune and slowly started to caress her back gently letting my fingers move up and down. I looked down to Jenny''s face to see her gazing up at me, I smiled and said good morning, she made to sit up so I held her still and asked if it was alright to stay as we were for a little while longer.

I still let my hand wander over her back reveling in a feeling of total comfort and luxury, after a little time felt a wet sensation on my nipple, looking down seeing that Jenny had decided to lick it, she then sucked it and started to bite it. I told her that if she didn't behave I would have to take her in hand and deal with her in a serious manner.

She sat up looked at me with eyes that betrayed a butter wouldn't melt in her mouth look and asked me what that might entail. I pretended to think about this then said let me see, I could put you over my knee and spank you or tie you up and ravish you.

she said she liked the sound of being ravished and spanked but didn't know which first.

I said before we go any further we need to make some ground rules to make sure you feel safe and can stop anything we do if you don't like it or you feel scared/uncomfortable, we agreed on a key word she could say and I would stop instantly, even if it was only so she could examine her feeling about what was happening. It seemed strange talking like that as we both sat naked but I put my arms around her and hugged her to me moving her so that she sat between my legs with her one arm round my back.

As I cuddled her I slipped my hand round her trapping her arm around me and caught hold of her other arm pulling it behind her effectively making it so she couldn't move. I pushed her backwards so that she was lying on her arms with her back arched over my left leg which moved her hips up as well. When she realised what I had done she started to struggle a bit and called me a bloody sneaky sod, grinning I said your not wrong babe.

I started gently rubbing and playing with her nipples gradually getting rougher as I went, pinching and pulling them. even pulling them up stretching the whole of each boob as far as it could be and holding it tight for several second before letting it go.

I kept my left hand holding her down as I explored the rest of her body caressing everywhere close to but not touching directly between her legs, after a while as I got close she started to try and move her hips to make me touch her, eventually she said please touch me this is driving me insane, I moved her legs a wide as I could and not hard but sharply smacked her directly over her pussy, she gasped and swore in shock, each time she said something I slapped between her legs. I went back to caressing her, starting on her boobs again, by the time I got to slip a finger in the top of her slit she was frantic and well wet. I didn't enter her directly but told her to lift her knees up, I move the tip of my little finger to her anus and pushed it in for a few seconds withdraw it and slipped my other fingers into her dripping pussy, I carried on like this for sometime, finger in anus, play with pussy, each time I fingered her anus I went a bit deeper or used the next finger until eventually I was inserting the whole of my index finger fully in to her tight little butt whole, Jenny was going mad trying to make me go faster.

I made Jenny turn over and kneel on the edge of the bed with her legs slightly apart and entered her from behind plunging deep and hard, banging away as hard as I could until I sensed Jenny starting orgasm I pushed my thumb hard into her anus and Jenny screamed and I thought I had gone to far. I went to pulled my thumb out and stop when I heard Jenny shouting don't stop, please don't stop, please don't stop. I came in a huge gush but kept going as hard as I could until Jenny collapsed forward flat on the bed and lay gasping, between her breaths and gasp I could hear her saying "god I enjoyed that".

I stayed lying next to her and she curled into my arms again, I asked if she was comfortable with what I had done. She said that when her ex had tried he just pushed straight in hurting her badly, but the way I had done it was enjoyable and that she would like to try again at some point.

Jenny asked what my plans for the day was, I said I had something's to deal with but should be finished about 5ish after that I had no plans. She said she was staying at home doing some housework but nothing else then asked if I would like to see her later on, I agreed to go for a drink with her but I had a condition, she must wear a skirt and that it must be no longer than mid-thigh. She took a long hard look at me and said "you are joking". I said no, that she has fantastic legs and I would like to see them on display more often, she tentatively agreed and I said I would pick her up about 8

At 4 I had a call from Jenny and I thought this is it she's changed her mind and was cancelling especially as her opening statement was damming me about the skirt, she then explained that she didn't possess a skirt and was now trying to buy one but was stuck between 2 and didn't know which one to choose, she described them to me and I said in keeping with her Goth style she should choose the leather one.

Saturday Night.

I arrived at Jenny's and she showed me the skirt of which I greatly approved, I told her I had a surprise for her but that she must promise to use it that night, she looked at me dubiously, I said trust me, please, and stepped towards her, gripped the bottom of the skirt and lifted it up round her waist and slipped her knickers down to her knees. During the day I had purchased a set of love eggs that were joined together, making sure she was moist. I slipped one into her pussy and the other into her anus, pulled her knickers up and her skirt down. I told her to walk round the room a bit and asked if they were comfortable, she said surprisingly enough yes. What I didn't tell her was that they were also remotely controlled vibrators.

We arrived in town and met up with a two of her friends from the night before, I wasn't sure how to act so just followed Jenny's lead, the three went to dance and I watched as the eggs started to do their job even though I had not turned them on yet, she came back to me her eyes shining in excitement. Her friends went to the loo and I asked how she wanted me to be towards her in front of her friends she leaned forward kissed me and said as a lover.

The remote had 3 buttons, one, two, and both, I wasn't sure where egg one was, front or back passage, so I waited until her friends came back and the girls walked to the dance floor. I pressed button one. Jenny's face was a picture, I waited a few minutes, then pressed button two, they had just started to dance, Jenny looking daggers at me, I thought what the hell and pressed the both button, I thought Jenny would fall over, her friends grabbed her arms looking really concerned. Jenny made her way back towards me calling me a lot of funny names, I sat there smiling. 

Bastard you could have warned me, I said that would have spoiled the surprise. I asked if she liked it, she answered by giving me a kiss and went back to her friends, after a few minutes I turned them off and she looked disappointed. Jenny asked me to dance with her so I shuffled round the dance floor with her for a slow dance. I pressed the both button and asked if she was ready to go, she almost dragged me out of the door.

We grabbed a taxi and she sat with her back the the driver and opposite me which surprised me at first, then she pulled her skirt up about 4 inches, opened her legs to revel that she had taken her knickers off during the night. I was sorely tempted to lean forward and touch her, but I thought that might be a step to far at this stage. Jenny giggled nervously, touched herself, then seemed to realise what she was doing and pulled her skirt back down.

We arrived at her house and she went straight to the kitchen and poured two very large whiskeys. I asked her what was wrong and she said that she had never done anything like that before and now was scared that I might have thought she was disgusting. I walked over to her, lifted her chin so I could look directly into her eyes and said it was probably one of the most exciting and erotic things I had ever seen and I was so proud and honoured that she trusted me enough to allow me to watch, she almost cried with relief 

I picked her up, carried her into the living room and put her on the sofa and asked if she would do it again for me. Slowly she pulled the skirt up and opened her legs, putting her fingers at the top of her slit closed her eyes and started to rub little circles getting deeper and deeper inside herself, she pulled out the love eggs and pushed her fingers in fully bringing herself to a full blown organism. In all my life I have never seen a sight more beautiful than a lady pleasuring herself, she lay there in total completeness of her own sexuality. I did nothing but waited.

After about 10 minutes Jenny stirred and looked at me. All I could do was to say "thank you, that was beautiful". 

Jenny told me to strip off, undressed herself - made me lay on the floor, sat astride me and said now its my turn. You are not allowed to touch me unless I tell you to, is that clear. I nodded my agreement.

Jenny started to stroke and squeeze my penis then lifted herself up and place the head just inside her pussy lips and sank slowly down until she had totally engulfed me using her vaginal muscles to move me up and down until I was close to cuming, she told me that I was not, under any circumstance, to ejaculate she then lifted herself off me and moved me until I was in line with her anus. Gently and with exquisite slowness she let herself take me, moving up and down slightly deeper with each down movement. I struggled hard not to orgasm, eventually she had taken my entire length balls deep, sitting there with a self satisfied look and started to play with her pussy again while rocking backward and forwards until she had an orgasm that seemed to last minutes and so hard she actually squirted love juice. By then I didn't have any choice in the matter and at the start of her orgasm I filled her anus. 

Jenny bent forward and I put my arms around her and we stayed like for almost half an hour.

We went to bed and slept.

Sunday Morning.

I awoke about 8.30 Jenny curled up beside me - I decided not to wake her and tried to get up to go to the loo but Jenny stirred so I just lay there until the need for the loo got to much - coming back to bed Jenny was awake so I sat on the side of the bed and asked her how she felt.

She said she was a little sore but had never felt so good about herself, I asked what she what she wanted to do about the situation and how she wanted to proceed. She asked how I felt, I said I was concerned about the age gap, but happy to continue until she, or circumstances, decided otherwise. She said the she had never so sexually satisfied and wanted to continue.

I got back into bed and we just lay there just cuddling until we got up for breakfast - I have seen her twice since then and we're just going with the flow for now to see how thing pan out.