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I was 22 when I had my first older woman. Despite having a loving and well proportioned girlfriend my own age. Lillian was well into her fifties when we first met. I’d worked with her in a large office but had only spoken to her a handful of times. A few months after leaving that job I was sitting in a bar when she shuffled in on high heels. I couldn’t believe it was the same woman.
The unflattering uniform I used to see her in had clearly been doing nothing for her curves. Now out in public, she was dressed like a woman half her age: caked in makeup, hair piled high, big dangly earrings and heels that made her big protruding arse stick out. Most blatantly of all, though, her tight dress had a very plunging neckline which exposed a full five inches of cleavage. She certainly knew how to attract cocks and mine was soon hardening as I watched her juggs jiggle towards the bar. I’d never seen a woman look more wanton in public. And certainly not one her age.
The place was almost empty so I decided to approach her. As we’d been colleagues, chatting her up was no problem. She was early and waiting for friends so we talked for about ten minutes. She mentioned her recent divorce which seemed like a come-on so I asked if she needed a lift home. She said she needed to go to the bathroom first.
I had actually meant a lift at the end of the evening but I wasn’t about to question anything that would delay the chance of getting my cock near such a massive pair of tits. If she wanted cock, she was getting it. I watched her extra large hourglass shape wiggle towards the bathroom.
Once she was out of sight, I came back down to earth and remembered I had a girlfriend. Claire was a fresh-faced blonde beauty of a 20 year-old who wore a 32F bra. I’d travel to visit her each Friday at her university (having graduated from there myself the year before) and we’d spend each wonderful weekend together. Did I really want to risk my two year relationship to try and fuck this older woman? In the end I let my cock decide.
As Claire and I spoke on the phone every night, I composed a text to her, feigning a migraine and saying I’d speak to her tomorrow. While Ankara travesti I pondered whether I should even send that text, Lil came into view, shuffling slowly back to where I was sitting.
I hit Send on my phone without taking my eyes off Lil’s shimmering udders. They were now jiggling with every step, spilling out of her dress even more than before. Like she’d purposefully adjusted them in the bathroom for my benefit.
“You ready then?” She asked suggestively as she arrived at my table, my eyes level with her cleavage.
“Sure,” I said, nonchalantly. Like I didn’t want to fuck her there and then.
While I drove her home, she kept adjusting her ill-fitting bra while complaining about her post-menopausal increase in bust size. This matter-of-fact talk was changing my cock from very hard to angrily erect. And her confirmation that she could no longer get pregnant sounded like an invitation to unload in her bareback. Something I was fully intending to do.
Once at hers, I followed her inside without a word, straight upstairs and into her bedroom. She sat back on her bed. I took this as a license to pull down the front of her dress, revealing more and more cleavage, until her tits flopped out completely. They were even bigger than they’d first appeared: long, wide and very floppy. Once I’d unzipped her dress down to her waist and undone the three straining hooks of her bra, her tits hung completely free and I saw that I was dealing with a truly gigantic pair of hangers.
Claire’s 32Fs were certainly very large, something often remarked upon, but they weren’t on the scale of Lillian’s. Unlike Claire’s firm, gravity-defying F cups, Lil’s were huge, wonderfully low-hanging and stretch-marked. Her bra claimed 42HH but was visibly too small for these boulders of immense tit-weight.
After gazing in wonderment, I pushed her back onto the bed to get on top of her. I scooped up her saggers in my hands. Pushed together, they were like two huge water-balloons, each bigger than my head.
With no pretence at kissing, I went straight into simply enjoying her titflesh; suckling her huge fat boobs; moving from one Konya travesti to the other while occasionally pausing to bury my head between them. She moaned encouragement.
I got her to sit up so I could test the weight and heft of her huge juggs; lifting, squeezing and generally mauling them. I’d never even seen a pair this size and couldn’t get over how heavy they were.
She started to rub my cock so I sat back as she unzipped my jeans and my cock sprang free. She then started giving me the most mind-melting blowjob I’d ever had. I’d been sucked-off many times by girls my own age but Lil’s technique was indescribable. But then she employed her tits, crushing my angry erection repeatedly between her incredibly soft fleshy globes.
After a few minutes of this, I really needed to fuck. I encouraged her onto all fours and hiked her dress up to reveal her huge fat rump which must’ve been three times the size of Claire’s. She was wearing no underwear and, as she was obviously too old to get pregnant, I sunk my thick eight inches straight into her wet pussy, balls-deep. I reached round to cup her juggs but in the doggie position they reached down to the bed. I just about managed to scoop them up without their weight pulling me over. And with my hands overflowing with titmeat, I started to fuck her.
Fucking Lillian was nothing like lovemaking with Claire. This was pure lust. No kissing. Just fucking a dirty old fat woman from behind; my hands squeezing her huge tits with each thrust. After a few minutes of this she fell flat down on the bed. My hands slipped from her tit mass and found her nipples. I tugged on them very hard and really started to pound her. She screamed into the pillow and I couldn’t hold back any longer. I spurted deep inside her at full depth and collapsed on her back from the most powerful orgasm I’d ever had.
Once we’d come to, we talked at length and she explained how her sex-drive had rocketed since her menopause. I was soon back on her for another round, this time with my head buried in titflesh while I came inside her. I stayed all evening, fucking her tits and of course having her on top while İzmir travesti she smothered me. I’d never been so turned on. My tender age and the immense amount of tit in my face kept me ceaselessly rampant.
After our initial session she gave me her phone number. I thought I might call her in a week or two but the next day I was ready for her again. I really couldn’t resist getting back on her as soon as possible. With another excuse to keep Claire at bay, I was straight round Lil’s the next evening. The second session was even better.
By my third visit, I was addicted. Of course, there was no reason to tell Claire and our romantic weekend went ahead as planned. I managed to not let on what I’d been up to but, of course, Claire’s perfect tits now looked small compared to Lillian’s enormous floppers.
To keep my affair a secret from Claire and my family (I was still living at home), I often left work early or claimed I had to work late so I could visit Lil on my way home. It was always a deeply satisfying session of sucking, tit-mauling and fucking.
And so the affair continued. I loved the contrast and enjoyed the purity and firmness of Claire for the weekend before being back on Lil the following Monday. Lillian knew about Claire but Claire never even knew Lillian existed. And so it continued: romantic love-making weekends with Claire, weeknight fucking with Lillian. They were such contrasting experiences and I saw no reason to give up either.
After two years of this perfect arrangement, Claire and I split when she went to work overseas. I then moved out from my parents and in with Lil. She became my “landlady” and the 30 year age gap meant no one ever suspected I was riding her.
Possibly because I was pulling hard on her nipples daily, her tits eventually began to sag beyond her navel and soon reached her waist. At one point I got her properly measured and was delighted to learn she was up to a 44J. I bought her a whole new set of bras to celebrate (though I kept the old ones as a momento).
After three years I had to relocate for work. I also felt it was time to move on and get hold of some new juggs. But Lillian had really raised the bar for size and attitude. She was just what I needed at that point in my life. She gave me a wealth of experience as well as a powerful imprinting to desire older women. And I would advise any young man to have an affair with an older woman.
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