Like a number of stories here, this happened a few years back so I might miss out certain parts but I will try and tell it the best I remember it…
I had recently turned 31 and had broken up with a long term girlfriend, moved to a new flat on my own and decided to just ‘enjoy’ myself for a while and blow off some steam. Therefore, with this in mind I threw caution to the wind and downloaded Tinder to see what happened….
So, a bit about me; 6ft, short brown hair, hazel eyes, in shape, not a model but not too bad to look at….well if you’re drunk and squint a bit..anyway, I got a few matches. Go Me!!
I ended up messaging with Annie who was in her late 40’s at the time, and chat was a bit flirty etc and we agreed to meet up for a drink. However, before the agreed date, one message exchange changed everything.
I had been out for a long work lunch which continued into the evening and so a few drinks had been sunk, and courage gained. As my drinking buddies started calling it a night I decided to head home too, this is where I sent a flirty message to Sally, nothing out of the ordinary or different from how things had been over the past few days; however, this night we were both a little more open to suggestion.
Sally had been out for the evening, although not drinking, and her route home took her past my area, so I jokingly asked if she was going to pop in, to which she replied saying she’d already passed, but she could drive back once she got to her local station and collected her car. Now, feeling confident from the drinks, I said that she definitely should.
When she reached her car she messaged to see if I actually meant it, to which I replied of course. We agreed to meet outside mine and no pressure if either of us didn’t ‘feel it’ or weren’t attracted to each other. However, I am glad to say that wasn’t the case or this story would end here!
She messaged to say she was close, so I sent and stood outside and saw a car driving up my road. She got out and the first thing I noticed was her pencil skirt and smart white shirt, she looked good! She looked exactly like her pictures, which was a bonus, 5’5″ or so tall, dusty blonde hair, brown eyes, probably c cup breasts, and a great arse, accentuated by that skirt. We had an awkward hug but both were pleased, so agreed to head inside.
Now, as soon as the door was closed we were all over each other, the flirty messages previously meant we knew exactly what the other liked, and after some passionate kissing and groping I lead her to the bedroom. I unbuttoned the shirt and gently removed it to reveal a nice white lacy bra, I then slipped off the skirt to be greeted with no underwear underneath, cheeky, I liked it. I removed the bra and lay her back on the bed and slowly moved my way down her body.
I spent a little while playing with her breasts, biting, nibbling, sucking her nipples, but I really wanted to move my face down, and feel the area my fingers were exploring and feeling get wetter. I kissed my way down her body and then as my face reached the top of her thighs I started to tease her my a few little kisses and just a flick of my tongue on her clit. She moaned as I started circling her clit with my tongue and slid in a finger. I continued playing and feeling her getting wetter, then I decided to remove the finger and replace it with my tongue, and that was definitely the right decision, she arched her hips as my tongue moved up and down tasting her wetness. She moaned and asked me to keep going, and as a gentleman, of course I did. I carried on tasting and teasing, making her moan softly until I heard her whisper ‘I’m going to come’, so with this I quickened my pace and movement until her body convulsed and she lay back on the bed panting.
I moved up the bed and kissed her passionately, so she could taste her own juices, which she loved, and she said how one good turn deserved another, so slowly moved her way towards my hard cock. Obviously I removed my clothes earlier, but that’s by the by. She took the tip in her mouth and started to circle the head with her tongue was one of her hands massaged my balls, she continued this for a bit as I told her how good it felt, and then moved her hand onto my shaft as she started to move her head up and down. Now, this is where her experience helped, as she was definitely great at giving head, and I definitely complimented her actions!
She continued at a slow and steady pace, before surprising me and really picking up the speed and, fuck me, that felt good. She managed to both quicken her speed and also tongue movements, which felt amazing. I told her how close I was to coming, and this seemed to help her find another gear, as she quickened her pace further I knew I was there so moaned, and as she felt me start to tense, she stopped and deep throated me, so I felt my cock and then come hit the back of her throat.
Somehow, she managed not to spill a drop and swallowed it all. She came up and said how she’s been looking forward to that for weeks.
We lay back for a couple of minutes and said how much we’d both enjoyed it, and as we were talking, my hand found it’s way back between her legs….However, as this is long enough already, I will save that for next time.
Source: reddit.com/r/gonewildstories/comments/hvsa5d/my_night_with_an_older_woman_mf