About 18 months ago I was looking for a generational fantasy, to have sex with someone in their 30's 40's 50's 60's 70's and maybe even 80[s. That was on my mind for over twelve months with passing enquiries but nothing really.
This is what has happened in the four months from November to February.
Things didnt happen exactly in order, my 50's was a neighbour tall dark smouldering she was having her 50th birthday a few friends over nothing outlandish, I was running late and by the time I had arrived the party was in full swing with the birthday girl well and truely in party mode , we hugged and kissed as we always do , chatted , said hi to the other guests , Her and her husband had just built a new shed at the back of the house , she wanted to show me ,she announced to everyone that she was showing me the shed , her husband just laughed , we walked around to the shed , it was close to the party I could still hear everyone talking, her husbands English accent stood out amongst all of the other people there. We chatted as she showed me the shed she was half leaning against it , she was wearing a white summer dress that looked brighter against her tanned body, she just looked at me half smiled lifted up her skirt and said I dare you to do me. To say I was taken by surprise was an understatement. My cock was already interested, I pushed her against the shed not to hard took my cock out and just pushed it into her . I could still hear her husband talking as I fucked her as quickly and quietly as I could one last push and I unloaded a wave of cum inside her . I pulled out put my cock away she just pulled her dress down and led me back to the party joking about the two of us getting married to her husband It wasnt a surprise party but it was for me.
My 30's was different a daughter of a friend I has known her since she was born she had grown up into a beautiful,intelligent, well educated well travelled young lady. Her and I had often had coffee and drinks together I enjoyed her company and we always had a laugh about the most silly things. I was visiting for the weekend and we had organised to go out for dinner, when I arrived she asked me would I mind having a night in . I didnt care we talked had drinks had nachos for dinner , she asked did I play games I said yes how about rock paper scissors , rock paper scissors became that with a shot if you lost the truths got more truthful the dares still appropriate, then she just asked me what I was thinking, she said its a game but you have to be honest ,She has a great body athletic with ample breasts but as she is small they probably look bigger, I thought for a second and said I was thinking I want to kiss you and put my hand down your shirt. A deafening silence then she leaned over and kissed me, not a great kiss but it was nice she grabbed my hand and put it on her firm breast. I slid my hand inside her strappy top , still kissing I slid the strap down her shoulder until her tit was exposed beautiful almost perfect her nipples were bright pink and getting harder as I squeezed them, we were still kissing but the intensity has risen I pulled away from her kiss to suck on her nipples her low gutteral moan almost made .me cum
I sucked her nipple hard and slid a hand inside her denim shorts , it was a tight fit , she undid her shorts and slid them down her thighs. One finger in then two I was almost biting her nipple off I had both tits out now . I pulled her shorts off I moved between her legs I was going to eat her pussy but just slid my cock into her instead she was tight but not super tight I pushed into her slowly , when all of a sudden I felt a flood of wettness on my cock , that moan and her hugging me as tight as she could. It felt like female premature ejaculation her orgasm slowly subsided, I pushed as deep into her as I could then slowly pulled completely out , It was still amazing
My 60's came in a pair but not together, I was visiting family the neighbour had come over to my brother in laws they had been drinking and partying all afternoon, she was just average looking tallish slim , when she said she was going home I offered to walk with her , we got to her front door she couldnt even get the key in the door I opened the door and we went inside I was just about to leave when she said I know Im going to regret this, she knelt down took my cock out and started sucking me off, it was a blow job that felt like she would want to get paid afterwards very matter of fact. She stood up pushed me back onto the lounge lifted up her salmon coloured mini skirt and straddled my cock she rode me until I came inside her she got off my cock and said she hated herself already and that I should go. I reminded her that we were having breakfast in the morning and left. She made breakfast we had a laugh about things and I had to leave
After I had gotten home and I was having a quiet beer I remembered I had told a friend I would mow her lawn for her , I went over mowed and cleaned up it was late I had just finished a beer and had decided to go home as I got to the door my friend asked would I like to stay, I just said sure I can stay for a while longer, she smiled and said no I mean stay stay. She is 69 small glamourous still stunning. She kissed me at the door wow what a kiss ,I cant even really describe it , it was like she was gently deep throating my tongue I didnt really want that kiss to end she led me by the hand to her bedroom everything in her house was perfect , we were just laying together talking , she kissed me again almost better than the first kiss, I touched her face and ran my hand over her clothed body she was tiny probably just over five feet in old language as we continued to kiss I unbuttoned her shirt her tits were small a little saggy but still sexy I pulled her towards me so I could unclip her bra pushed her shirt and bra off tanned all over I played with her tits as we kissed , I could reach her little skirt and panties easily because of the height difference , I stopped kissing her so I could kiss her nipples I was slowly sliding my fingertip over her clit she couldnt seem to lay still so I must have been hitting the spot I pushed one finger into her her, she was so tight my finger felt like it wasnt even going to fit inside her , while I very slowly fingered her super tight pussy , she reached down and pushed my shorts down past my cock she wrapped her hand around my cock and said OMG this will be a challenge she moved her mouth down and over the head of my cock my cock is big enough but looked massive because she was so tiny , the head of my cock disappeared into her mouth it was like the kiss but on the head of my cock ,like the kiss I had never been sucked like this it was like she could use every muscle in her mouth seperately, my cock continued to disappear into her mouth halfway, three quarters of the way all the way her nose was pressing against my stomach it must have been almost all the way down her throat , she held my cock all the way down her throat then some how managed to make me feel like she was massaging my cock with her throat and her mouth I came harder than I have even cum in my life , my whole body shook, she just grabbed my arse and held my cock there down the back of her throat . She slowly pulled her head back, my cock was glistening I kissed her I could taste my cum still in her mouth.
I took a deep breath smiled at her and kissed my way down her tummy to her shaved pussy I licked the length of he pussy sweet like honey I put my finger back inside her and slowly licked her clit , I squeezed two fingers inside her she was wet I grabbed her clit between my teeth and flicked my tongue over it , with my fingers and tongue working together she started that half rolling around and moaning her legs were starting to shake , I turned her over and ran my tongue along her firm arse still with the fingers inside her they moved in and out more freely as she got wetter and wetter , she was pushing back against my tongue and my fingers, her legs were shaking and I could feel she was close to coming I was so sure that my cock would not fit but it was now or never I turned her back over moved between her legs and rubbed the head of my cock along the length of her wet pussy. I pushed slowly I had to push a little harder to push the head into her the head went in and her pussy wrapped all around it I pushed half in , she said all of it I pushed my cock in to the hilt her pussy was so tight it felt like her mouth but tighter, I pulled back as far as I could without the head popping out then slowly all the way in, I changed to short jabs about three or four followed by one deep thrust it was working She had her legs and arms wrapped around me holding me as tight as she could , then three deep thrusts then short thrusts, she was saying yes yes yes raking her fingernails across my back I was just pushing in deep and long now , she half screamed raked my back with her nails and bit my shoulder as hard as she could with her legs wrapped tightly and shaking around me , I thrusted into her hard for as long as she was coming . The pain from her biting and her nails was excruciating but hot as fuck I felt her legs loosen from around me I stayed inside her as she slowly let go of me and put her head back on the pillow , glowing with a red tinge of my blood on her lips . We just stayed like this until my cock went soft , she was so tight still,my cock popped when I pulled it out . We spent the night I woke up thinking I was having a wet dream but she was just sucking my cock I came almost straight away, she was having visitors so I left we still see each other
my 70' was a cute encounter an older friend who had lost her husband about 25 yeas ago she is a character , loves a drink loves music is flirty but nothing trashy she is 77 with a few extra pounds but still classy
I was doing some repairs on her house and she was having a few wines while I was working , when I finished we had a few drinks me a champagne or two her white wine. I had to go home to pick something up so I offered to buy takeaway and comeback for dinner.
We had joked about sex and her fantasy she didnt really have one but she did say once that her husbands penis was the only one she had ever had.
I got back with the food she had just kept drinking while I was away we had a nice dinner had the music on she was sort of flirting but in a way someone her age would flirt more drinks and time to leave , I leaned over to kiss her goodbye as she was sitting in a chair , she always grabbed my face when I kissed her she did that but kissed me a bit longer than she normally does. I slipped my tongue into her mouth more for a bit of fun than anything, expecting her to tell me I was cheeky, it surprised me but she reciprocated with a beautiful passionate kiss, I just kept kissing her it was nice not erotic she was still holding my face I thought what the hell and grabbed one of her tits which was substantial but quite firm for someone in their 70's she didnt complain moaned sofly so I just kept softly massaging her on the outside of her top the kiss went up a notch as did her moaning so I slipped my hand inside her top big firm tits with huge nipples that I could feel getting hard. She had only touched my face , my cock was hard so I got it out and put her hand around it as we kept kissing and I squeezed her nipple she awkwardly stroked my cock. I realised at this point that I could make love to her but had another idea.
We stopped kissing and I guided her head towards my cock as I was basically still standing next to her , she certainly wasnt a professional and I was not going to pressure her if she didnt want to go any further , she was still stroking my cock she giggled and ran her tongue along the eye of my cock I kept softly playing with her nipple she licked around the head and then rubbed the eye of my cock with her thumb I must say I was rock hard , she reach around with her other hand and put it over my hand that was inside her top and slowly removed my hand from inside her top. I thought this was it for the night . she let go of my cock and reached up and grabbed my face and kissed me deeply and passionately and even romantically. I smiled at her and then she said you sit down here and she got up out of her seat I sat down cock still out and still hard she sort of half sat down on the floor took my cock in her hand again giggled again and ran her tongue over the eye then under the head then along the full length of my cock, she moved her hand halfway down my cock put her lips over the head and went down on my cock , it was gentle and romantic no teeth no deep throat just a gentle up and down the blow job you would probably expect from someone from her era , she was sort of on her knees now both hands wrapped around my cock sliding up and down with her head and mouth doing the same she just kept sucking and stroking It caught me a bit by surprise as I suddenly let a load go in her mouth I grunted and moaned as she just continued to suck softly and gently swallowing every drop of my cum as well. She sucked me until my cock went soft in her mouth. She licked the tip of my cock and said you seemed to like that and now you are number two we laughed I kissed her again and I realised she had fulfilled her fantasy which made me feel fantastic about what we just didIm still looking for my 40's but I am not complaining
