A mid summers day back in the mid eighties. I had not long passed my driving test and I was driving an old Singer Vogue (cheap but very useful with good back seat). It was about midnight and I had been out with friends but after I dropped them off at home I drove to the next town and was cruising up and down the high street to see if there was anyone interesting around. The high street was on a big hill leading down to the sea front and it was a one way system leading down so I was taking a back street to drive back up to the top to drive down again. The high street was deserted and there were very few cars around as it was mid week but after about three circuits I spotted a woman in a shop doorway looking at stuff through the window. She was obviously a lot older and she was wearing a tight thin yellow wollen top, black pleated skirt and heels. As I slowly drove past I saw the obvious size of her tits and I was rock hard in seconds!

I slowly moved down the street a little way and then parked at the side of the road and slowly walked back up the street towards her. As I got closer so was really not looking at anything in particular and she looked a little spaced out. She was also older than I had originally thought and I would have guessed in her late sixties when I could see more of her. Shoulder length hair and lovely makeup and she seemed to be in a world of her own so as I have never been shy in coming forwards I stopped and said hi. She turned towards me and smiled then apologized thinking it was someone else and I could see then that she was at least a little tipsy. Perfect! My eyes were all over her big tits and I could see that she was wearing a lace deep-plunge bra as the material could be clearly seen now through the thin wollen top. I have always been very good at conversation so it was easy to find out that she had been out with friends (obviously had drunk a little more than intended) and the conversation really was all over the place as she was tipsy enough for me to really get a good look at her (I was absolutely solid!) and we chatted about the summer, evenings out, the football pools (no idea, but it was the eighties...), just about anything to keep her engaged in conversation. Basically at this point I was looking at every part of her I could so that I could have a really good wank in the car on the way home at the very least.

Fuck her big tits looked perfect under her thin top and when I asked where she lived she told me that it was a flat on a side road at the top of the high street so I said I would walk with her if that was ok. She smiled and we set off and as she was a little unsteady I took her arm and she giggled. As we walked she started to lean into me and she was a little shorter than me so I had a perfect view of the movement of her big tits under her top. I was so hard that it hurt!

Time for second base... As we walked on we came to a womens boutique clothes shop with a deep recessed doorway so I carefully led her into it so that we were out of view and then pointed out a few things inside that I said would look good on her. There was more giggling and she swayed gently then I turned to her and said that I loved the material of her top. She looked down at herself and I said that I bet it was very soft and expensive and she said that it was so I just came straight out and asked if I could have a feel. She said yes so I gently put my hand on the side of her left tit with my right hand and felt it gently with my fingers. She giggled and told me that I was a very bold young man and giggled again.

Time for third base... At the very least now my wank on the way home was going to be very good but before settling for that I pushed a bit further. I took her arm again and led her a little further up the deserted high street and a little way up was a narrow dark side road so I led her by the arm into it. She told me that we were going the wrong way but I said that we wouldn't be a minute and I led her a little way up to some lockup garages. I picked the most hidden one and led her up against the wall well out of view then positioning her up against the wall I asked if she minded back there, when I felt how soft her top was and she said that I was a very bad boy and giggled and I moved my hand back up again and told her how soft it felt and as she dodn't object I cupped her tit and gropped it gently through her top. VERY big and soft and I could feel myself leaking now. I asked her if that was ok and when she giggled again I reached down and pulled the front of her top up so that it was over the top of her wonderful white lace “classic” deep-plunge bra and her entire vast cleavage was on full show to me! Now I groped her huge tits through her bra and after a moment she said that she had better be getting home. I leaned into her and kissed her pushing my tongue gently into her mouth as I carefully lifted the tit right out of the bra cup and let it hand down. HUGE heavy soft tit with a huge areola and I took it in my hand and squeezed as I kissed her. My thumb soon her her nipple bullet hard then she pulled back and told me that she wasn't sure this was a good idea then we kissed again as I pulled the other tit out of her bra so that her huge tits were hanging down exposed to me. I said it was ok and no one could see us then I leaned down and sucked her nipples hard. Her nipples were HUGE too!

Time for forth base... At the very least me wank was going to be awesome now but I wasn't ready to settle for that just yet. I moved back up and kissed her and sucked her tongue then I wrapped my hands around her lovely round bottom under her skirt and had a good feel as she said “you won't tell anyone will you?” I told her of course not and then my hand moved around the front, lifted her pleated skirt and I cupped her cunt through her pantyhose and panties and a few moments later I slipped my hand under her underwear so that my hand was on her lovely hairy cunt and two of my fingers were inside her surprisingly (to me at the time) tight cunt and then I unzipped myself and pulled out my solid cock and moved her hand down to it.

Fith base... I fusked her twice that night without a break and even got a wank off her her when we got to her place. I explored loads with her over the next two months including one of her friends too (without her knowing).

The right conversation, a little flattery and not being in a rush was the lift lesson I learned that night and it was a lesson that's done me well over the following years with older women.