I was 24 and fresh out of University, and started a job with a fairly large company.
My time with the ladies at uni hadn’t been prolific – I’d slept with 2 people in the 4 years. My main reason for this spell was my self-confidence…I had none! I was about 15 stone (210lbs or 95kgs for those in the new world) heavier than I am now. Girls rarely looked at me, and those who did would let my advances down with “I bet you give great hugs”. So I rarely tried anything.
I started work and there weren’t any in the office of a similar age to me. There was one woman in the office who caught my eye – Claire.
Now the first thing I’ll say is that Claire was not technically a MILF…she had no kids, however she was 12 years older than me and very attractive, so MILF will do for a description.
Not long before I started with the company, Claire’s husband had walked out on her and moved to Portugal to live with a girl he met on a boys holiday.
About 4 months after we started there was a work night out as one of the guys closer to my age was leaving. As the night drew on, it came down to 4 of us left in the pub at closing time – 2 other guys, Claire and myself. Claire decided we were heading for the takeaway and then going back to hers to carry on the party. We lost one guy on the way to the takeaway, then the other guy ended up going to meet his girlfriend so Claire and I found ourselves in a taxi heading for hers. It was at this point she said we needed to be quiet as it was actually her parents house we were heading for – she’d moved back in after selling her own house.
I didn’t think anything of it – I was so accustomed to not ‘going on the pull’ that I took everything at face value…I was going back to hers to eat my chips, have a drink then head home. And that is exactly what happened we sat at either end of her couch with a gin and tonic, I finished my chips and she had her pizza. We chatted and she started asking if I had a girlfriend etc. Eventually she excused herself and I heard her going upstairs.
She came back in a few minutes later, and this is a good time for a description – Claire was around 5ft3/5ft4, she had jet black hair in a bob. She taught a couple of aerobics classes at a nearby gym so she had a well toned body. Her outfit that night was a knee length skirt, a blouse with a vest top beneath it, and she had on a pair of stiletto boots – leather, with red soles and a 3/4 inch heel on them. She looked good, very good. When she came back into the room, she had taken her shirt off so was in the silky vest top which was quite loose so there was a lot of cleavage on show as she moved around.
She sat next to me on the couch and tucked her legs up to the side so she was leaning into me even more. There was a split up the side of her skirt which showed a lot of her thigh. She started to tell me about her divorce and how she was only just starting to get over it.
As she spoke she started brushing my thigh with her hand and eventually, after a bit more talk, she took my hand and placed it on her leg. Whilst I don’t think she actually said these exact words, I think the gist of her conversation was “we can help each other out”.
She kissed me which, for some reason (probably ‘rabbit in the headlights’), I let her do whilst I stayed rigidly still. After what felt like years, I kissed her back and started to let my hand move. The skin on her thigh was silky smooth, and I tried to work up and under her skirt but it wasn’t working due to the way she was sitting, so I went up and under her top. Her breasts were a good handful, and I massaged them as we kissed. Her hand had moved up my leg, unzipped my jeans and was rubbing my cock through my boxer shorts.
Eventually, she broke the kiss and stood up. She told me to take my jeans off, which I promptly did. She pulled her vest top off and popped her breasts out of her bra. She then pulled her skirt up to her waist – in my mind now it was a very sexy side to side swaying movement, however I think in reality it was just pretty straightforward pull. Her small patch of pubic hair confirmed that jet black wasn’t her natural colour, and she told me that she hadn’t gone commando that night, she had left her panties upstairs. She reached under her jacket that was still on the couch and produced a condom that I’d missed her bring back down stairs with her, and she handed it to me as she leaned down and took my already rock hard cock into her mouth. She kept the tongue firmly on the shaft as she worked it. She told me to put on the condom, which I did in about 2 seconds. She straddled me and lowered herself onto my cock – I had never and have never been in a pussy as warm as hers. We both remarked at the same time how hot it was, so I’m guess my dick was radiating heat too (no wonder, it felt like every drop of blood I had was in it). She started gently rocking, reminding me to be quiet because her parents were asleep upstairs.
This was the point where I think I got the boot fetish – the smooth leather rubbing against my legs on either side as she rocked felt amazing. My hands, which had moved from her breasts to her ass, moved down and started rubbing the boots.
“Grab my heels” she said as she started to ride harder. I did and I started to use them as leverage as I thrusted up. I wish I could tell you, readers, at this time that we fucked for hours in this position…I lasted about 30 seconds before I filled the condom. She reassured me it was ok despite my repeated curses and swears.
I’d never had an issue with going early before, but then I’d never been with someone as sexy as Claire before. In the movies, this is the point where the girl usually walks off leaving the guy sitting embarrassed however she wasn’t done. She stood up off me and lay on the opposite end of the couch instructing me to eat her pussy.
She directed me, telling me where to touch her and when – I didn’t mind being used like a sophisticated sex toy. She had me alternating between licking and sucking her clit, and when I slipped a finger inside her as I licked, that’s when her moans got louder and her boots wrapped around my back, pressing into me. I stretched her to 2 fingers, then as I felt her start to tighten, I forced a third in. All the time I was still working at her clit with my mouth. I could hear her muffling her moans with what I later realised was a cushion, and she orgasmed hard, soaking my fingers as she did so. Before I realised it, I had pushed my fingers deep into her mouth, making her lick them clean.
As she lay breathing heavily, I stood up, looking down at her. Her chest was shiny with sweat, as was her face. My cock was now back up at attention, and I asked if I could fuck her in that position. She nodded and produced another condom from her jacket. I remember her telling me to be very slow when I entered her, and she moaned and shook alot as I slipped inside her again. After she got used to me being on, she nodded and said I could start. I had one knee/leg supporting me on the couch, this was a completely new position for me – being a big guy at the time, I could only ever go on my back with the girl on top however I was mindful that I didn’t crush poor Claire.
I pulled one leg up and onto my shoulder, this time I couldn’t only feel the leather, but I could smell it too. I wanted to start kissing and licking the boot there and then, but decided that was a bit weird for this particular session. I pulled the other leg up on the other side and I went for it as hard as I could – for the first time, I had control in sex and I went to town with it. The noise of my balls slapping off her was amazing, and she had the cushion back over her mouth muffling her moans. I pulled it away, I wanted to see her face as I came in her again. She grabbed my hand and covered her mouth, staring into my eyes as I reached my crescendo. I came hard again, my legs shaking as I carried on pumping into her. I pulled out and took a step back before dropping to my knees.
We dressed quickly, aware that the noise increased towards the end and hoped we hadn’t woken her parents. She told me I had to go, and ushered me to the door. Just before she opened it, we had a long kiss goodnight.
I didn’t stay in that job much longer, and neither did she. We never hooked up again, but she did mention it a couple of times in a way that made me think she’d be up for it again. I later learned that I was one of a few guys who she had ‘enjoyed’ her single life with. Last I heard from her was around 6 years ago and she appears to be with someone else and has a kid.
Aside from the nice memories of that night, she also left me with a boot fetish and I try to involve them in sex as often as I can – it can be as simple as the lady wearing them (as mentioned in my Anal story from a couple of weeks back), to going for a full on boot worship session.
Source: reddit.com/r/gonewildstories/comments/58o0ur/these_boots_were_make_for_walkingand_fucking_how
Very hot story! Love the boots.