1st time shoes and sex with a female

A shoejob, or heeljob, similar to a handjob, requires the involvement of a female. There are various ways a woman can be involved, whether she is wearing shoes while they are being cum on, she is jerking someone off into her shoes, licking cum off her shoes, etc. Shoe masturbation, shoe cumming or shoe fucking requiring no female involvement belongs in the Shoe Cumming Forum below.

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droid1959
Posts: 572
Joined: Fri Aug 06, 2010 9:59 am

1st time shoes and sex with a female

Post by droid1959 »

I'm curious to know others 1st time where shoes and sex with a female finally all came together.

Mine was in November 1988, ten years into my 1st marriage at the age of 29. My wife back then worked in a bank or office and wore heels and pantyhose every work day. Yet, I never made my desire for her narrow size 7s until the day after Thanksgiving. We went to dinner with my mom and dad, my wife wore a long tapered black leather skirt with a red sweater and red snakeskin pumps. And OH did it work on me!

Back home we were getting intimate in the den, and I finally mustered up the guts to ask her to wear shoes while we fucked. She was all for it and told me to go get some heels for her. I came back to the den, knelt on the floor between her thighs, and raised one of her feet to slide the red snakeskin pump on her lovely foot. But I made sure my cock head was between her lips so as I slid the pump onto her foot I also slid my cock into her open wet pussy. Then to slide the other pump on her foot and pulled my cock back out till just the head was on her open pussy lips. As her foot slid into the pump I pushed my cock in deep into her pussy. Then the real fucking came on big, pumping her with her heeled feet over my shoulders. After that night, shoes and heels became a common part of us fucking.

In fact, near a year later she invited me to fuck her in the ass, and again those same red snakeskin went on her feet before I experienced my first butt fuck. I will never forget her telling me, "Fuck me! Fuck my ass! CUM IN MY ASS!"Ahh memories. I am still good friends with my 1st wife and even my 3rd wife has become friends with her.
theref
Posts: 31
Joined: Sun Jun 20, 2021 11:21 am

Re: 1st time shoes and sex with a female

Post by theref »

i had always had a fascination with heels and stockings. i can recall watching my teacher at infant school dangling her heels under her desk. once when she was walking around the class i did the ''drop a pencil on the floor and look up the skirt'' trick. i must have been no more than 8. moving into my teens the fascination was still there and i secretly drew fantasy drawings of feet in nylons and heels. ever since, i have had a fetish for all things of a similar vein but only with slender heels and particularly of small feet with high arches in nylons. my first wife didnt really ''get it'' but once i had divorced and i had discovered a whole new world of sexy women out there i really got into my stride. i met a very special woman who simply took my breath away. simply beautiful in every respect but as we got to know each other and found new ways to please each other, she opened my eyes to the wonderful world of sexual expression. she had lovely size 4.5 feet, and knew just how to use them on me. usually she wore stockings or holdups when in bed, and one of our favourite games was to play 'shoe shop' as she called it. it involved her trying on all her high heeled shoes and parading in front of me, encouraging me to help her try the various styles on. i would play the part of the shop assistant who eventually couldnt stop myself from running my hands up her legs to find her moist pussy. even thinking of it makes me hard to this day. i used to love buying her new styles to wear and one day we went shopping together. in the shoe shop she was trying on a couple of pairs and walking up and down to ''try them on''. but really of course to show them off in front of me. the staff were a bit bemused but oh my, how horny it was. we bought the shoes and practically ran to my flat where we leapt into bed so i could explore her toned legs further. i recall that this was the time she told me after her climax that she ''didnt know orgasms like that existed''. she thrashed around so much at her orgasm that the shoes came off her feet , with only the ankle ties still in place. how i miss her. my own best ever climax came with the same lady a few months later. she used to love to feel slutty and see the effect she had on me and one day she told me to pick her up on the corner of her road and see what happens. i duly did so. she was dressed in a leopard print coat, fishnets and black ankle boots. when i stopped my car she walked up and said thru the window 'looking for business darling?'' i nodded, she got in and told me her price. i stuttered and said i have cash at home. ok then. off we went making up small talk as if we didnt know each other. she played the part to perfection. she lit a cigarette -she didnt smoke - and was every inch the perfect escort. the perfect mix of slutty whore and lady. i actually paid her the cash and then we got down to business. i think playing the part gave her completely free range to express her own fantasies. anyway, to the point of the story. as we fucked she still wore the black leather ankle boots. somehow we managed to keep penetration with her legs straight against my chest and suddenly hwr boots were in front of my face. i kissed and licked them and something made me take them off. she smothered my nose and mouth with her feet and as i inhaled the aroma of the nylons and leather i instantly came with a force i have never known before or since. and trust me i have tried many many times to replicate the effect. there isnt a woman alive who doesnt look better in nylons and stilettoes
theref
Posts: 31
Joined: Sun Jun 20, 2021 11:21 am

Re: 1st time shoes and sex with a female

Post by theref »

i had always had a fascination with heels and stockings. i can recall watching my teacher at infant school dangling her heels under her desk. once when she was walking around the class i did the ''drop a pencil on the floor and look up the skirt'' trick. i must have been no more than 8. moving into my teens the fascination was still there and i secretly drew fantasy drawings of feet in nylons and heels. ever since, i have had a fetish for all things of a similar vein but only with slender heels and particularly of small feet with high arches in nylons. my first wife didnt really ''get it'' but once i had divorced and i had discovered a whole new world of sexy women out there i really got into my stride. i met a very special woman who simply took my breath away. simply beautiful in every respect but as we got to know each other and found new ways to please each other, she opened my eyes to the wonderful world of sexual expression. she had lovely size 4.5 feet, and knew just how to use them on me. usually she wore stockings or holdups when in bed, and one of our favourite games was to play 'shoe shop' as she called it. it involved her trying on all her high heeled shoes and parading in front of me, encouraging me to help her try the various styles on. i would play the part of the shop assistant who eventually couldnt stop myself from running my hands up her legs to find her moist pussy. even thinking of it makes me hard to this day. i used to love buying her new styles to wear and one day we went shopping together. in the shoe shop she was trying on a couple of pairs and walking up and down to ''try them on''. but really of course to show them off in front of me. the staff were a bit bemused but oh my, how horny it was. we bought the shoes and practically ran to my flat where we leapt into bed so i could explore her toned legs further. i recall that this was the time she told me after her climax that she ''didnt know orgasms like that existed''. she thrashed around so much at her orgasm that the shoes came off her feet , with only the ankle ties still in place. how i miss her. my own best ever climax came with the same lady a few months later. she used to love to feel slutty and see the effect she had on me and one day she told me to pick her up on the corner of her road and see what happens. i duly did so. she was dressed in a leopard print coat, fishnets and black ankle boots. when i stopped my car she walked up and said thru the window 'looking for business darling?'' i nodded, she got in and told me her price. i stuttered and said i have cash at home. ok then. off we went making up small talk as if we didnt know each other. she played the part to perfection. she lit a cigarette -she didnt smoke - and was every inch the perfect escort. the perfect mix of slutty whore and lady. i actually paid her the cash and then we got down to business. i think playing the part gave her completely free range to express her own fantasies. anyway, to the point of the story. as we fucked she still wore the black leather ankle boots. somehow we managed to keep penetration with her legs straight against my chest and suddenly hwr boots were in front of my face. i kissed and licked them and something made me take them off. she smothered my nose and mouth with her feet and as i inhaled the aroma of the nylons and leather i instantly came with a force i have never known before or since. and trust me i have tried many many times to replicate the effect. there isnt a woman alive who doesnt look better in nylons and stilettoes
theref
Posts: 31
Joined: Sun Jun 20, 2021 11:21 am

Re: 1st time shoes and sex with a female

Post by theref »

droid1959 wrote: Fri Mar 11, 2022 2:20 pm I'm curious to know others 1st time where shoes and sex with a female finally all came together.

Mine was in November 1988, ten years into my 1st marriage at the age of 29. My wife back then worked in a bank or office and wore heels and pantyhose every work day. Yet, I never made my desire for her narrow size 7s until the day after Thanksgiving. We went to dinner with my mom and dad, my wife wore a long tapered black leather skirt with a red sweater and red snakeskin pumps. And OH did it work on me!

Back home we were getting intimate in the den, and I finally mustered up the guts to ask her to wear shoes while we fucked. She was all for it and told me to go get some heels for her. I came back to the den, knelt on the floor between her thighs, and raised one of her feet to slide the red snakeskin pump on her lovely foot. But I made sure my cock head was between her lips so as I slid the pump onto her foot I also slid my cock into her open wet pussy. Then to slide the other pump on her foot and pulled my cock back out till just the head was on her open pussy lips. As her foot slid into the pump I pushed my cock in deep into her pussy. Then the real fucking came on big, pumping her with her heeled feet over my shoulders. After that night, shoes and heels became a common part of us fucking.

In fact, near a year later she invited me to fuck her in the ass, and again those same red snakeskin went on her feet before I experienced my first butt fuck. I will never forget her telling me, "Fuck me! Fuck my ass! CUM IN MY ASS!"Ahh memories. I am still good friends with my 1st wife and even my 3rd wife has become friends with her.
to follow on from my previous reply, i see with interest how your wife wanted you to fuck her in the arse. i have a theory that a lot of ladies deep down desire to be slutty on occasion, and the heels are the first step in this process. my lady in question got more and more bold and frequently pretended with me to be an escort. sometimes we would meet in the bar of a hotel and introduce our ''characters'' , each time pertending to be a new person.. after paying her the cash -this was always part of the game to make it real - we went to the room i had booked. one day she said to me that she offered anal as a service but it was extra. !!!! i willingly paid up. the woman was a minx. i was so excited i came the instant i entered her arse. ''no dont fucking cum yet!'' she scolded me but it was too late. with a wicked grin she said we would just have to try again when i was ready. which we did. and with a dildo in her pussy as i fucked her arse she came as she told me to ''fuck me hard. harder''. her other main fetish was bondage. with her tied up i was allowed to do anything i wanted to her. my favourite was to tie her to the door with her arms above her head, and blindfolded. always she would be in stockings and very high heels. these emphasised her lovely legs and arse cheeks. it would give me complete access to her body and turning her round to face the door i could run my hands and tongue up her legs to her cheeks and eventually to tease her arse. it was the most intimate thing i could imagine to rim her arse and hear her moans. it will always be a regret that we broke up when i was going thru some very dark times. we still meet for coffee sometimes but she is now married and i wouldnt do anything to spoil our friendship or offend her.
droid1959
Posts: 572
Joined: Fri Aug 06, 2010 9:59 am

Re: 1st time shoes and sex with a female

Post by droid1959 »

I agree totally. My 2nd wife would never allow an R rated movie in the house. I could never say "pussy", she wanted me to say vagina. Once she said "pump me with your hard cock" but would NEVER say the word fuck. She would never show any chest cleavage when out. But, she loved to wear very short skirts with pantyhose, or a slightly longer dress or skirt with thigh high stockings. We were in Tampa FL once on a business trip. Went out for dinner, her wearing a very short skirt, tan fishnet thigh high stockings and tan peep toe slingback heels. I'm sure many men in the restaurant and bar could see the lacy tops of her stockings and she willingly let it happen. We fucked hard, twice back in the hotel. I recall thinking, after the second fuck, I should have put her heels back on her feet, told her to model them for me in the hotel room now with no panties on, and then I should have said "we are going to bar for drinks but you cannot wear any panties." And I bet she would have done it.

The night when I fucked her ass, our 1st Valentine's dinner, she wore a very short skirt, pantyhose, and red strappy pointy toe heels, and we're out for drinks and she was not trying to make sure the darker control top of her pantyhose was not showing. Back at her place, we're fucking hard doggy style, when she says "want to try my mystery hole?" Was her way to ask me to fuck her ass, though she'd never said it that way. We lubed up and I slide in hard, finishing when I said "I want to fill your ass up to my balls!" She was all for it and I exploded up her tight little ass. By the way she was a tiny size 2, only 5'-2", little size 4.5 feet, great looking ass in pantyhose.

Another time out for dinner in Green Bay on a Sunday night after a weekend motorcycle trip, a long weekend where she sucked me off three times (she always swallowed) and fucked at least three time. This time she had on a striped black/white dress, black thigh high stockings and pearl white toe cleavage pumps. She was teasingly eating bread sticks like she was sucking my cock. I think back to that and should have told her "give me your panties, right here, right now." and she would have done it. I took pictures of her outside on a bench, and I bet if I had told her to flash her legs open she would have too. After dinner back at her place, I recall laying on her bed, she is straddling me in the stockings and heels bent over sucking my cock. Sucking so good I again exploded in her mouth. Thought that was it, but before I could go soft she sat on cock and rode me cowgirl style with her lovely ass bouncing onto me, still in her heels. Within minutes I popped another load in her.I think through that weekend she sucked me off four times and we fucked at least four times. And I could make her cum and cum.

After we married in Oct 2002 till our divorce in July 2008, We maybe fucked eight times the 1st year, fucked a few times per year till 2005, then nothing. She went totally cold on me, and it wasn't menopause, she was just an angry woman. Glad she is out of my life. But for 1999 to 2002 she was a great physical partner that I know would have done DP (dildo in her pussy, my cock in her ass), and I bet I could have encouraged her to flash in public as I feel she had a voyeur side she didn't realize. Early on, Dec 1999 we're driving back from a Christmas dinner. She was wearing a nice dress, snakeskin open toe sandals and stockings. I was fingering her pussy on the drive, she had her heels up on the dash, spread wide. I said that looks so hot, too which she turned on the overhead light in the car as I fingered her to cumming. We ended up in a parking lot, she climbed on top of me to ride my hard cock, 1st time fucking her in heels and nylons, of many times. After we married, heels for fucking maybe twice.
theref
Posts: 31
Joined: Sun Jun 20, 2021 11:21 am

Re: 1st time shoes and sex with a female

Post by theref »

hey droid. i loved reading about your exploits with your wife. very horny stuff. my favourite lover who i had so many games with was a similar size to your wife, and she was very athletic with strong calf muscles -a particular fetish of mine - and a wonderful arse. she was the woman with whom i could finally learn what sex - and lovemaking -was all about. and we explored together as she was leaving a dead marriage just like me. she used the ''escort'' game to be able to fully express her sexuality. she pretended to be someone else, so the normal rules of behaviour didnt apply. one night she wanted to explore being ''forced'' to have sex. we met in a bar and i ''picked her up'' each of us playing roles of strangers. i remember that night i pretended to be a pilot!!. she wore tan hold ups with a tight black pencil skirt and black heels on her dainty feet. our conversation as i tried to convince her to come back to my place must have sounded ludicrous but i simply didnt care. i had to get her in bed and fuck her. we went back to mine and we kissed long and hard. i caressed her legs and spent time kissing her legs and the back of her knees until i eased her shoes off so i could savour the scent of the shoes on her feet. i put her shoes back on and this was where she started to play her game for the night. she said she wanted to stop. but of course this was my sign for me to carry on and ''force'' her into sex. bending her over the edge of the couch i shoved my cock in with absolutely no finesse or foreplay. she was wet of course so i entered her easily and after only a few thrusts i came hard. wasnt my favourite session by a long way becuase i totally love turning a woman on. making her come was always just as exciting for me as my own orgasm. deep down she loved being a tart for me. i could get bher to dress for me just the way i wanted -al;ways stockings or hold ups with heels - and she could act out all her own fantasies by being her alter ego. one night she posed for photos for me. wonderful. black thong, black hold ups and the highest black heels she had ever bought. after posing for about 30 minutes she said i could pay her extra if i wanted sex. well what was i supposed to do???!!! cash was exchanged. she said ''use me, do whatever you want with me''. i made her stand in front of me so i could worship her legs and feet in those ridiculously high heels. turning her round my tongue explored her thighs , higher, util i parted her arse cheeks and probed her arse wioth my tongue. her knees gave way and she knelt on the edge of the couch. 'fuck me' she said. i want to be worth every fucking penny''. my cock teased her pussy lips from n behind but she wouldnt be teased. ''fuck me'' she said again, this time louder. so i did. i entered her very roughly. she made a sort of ''nnnnngg'' noise and moaned ''HARDER'' . As i thrust hard and deep she started to climax so the word became ''HAARRRDRRRRRRRAAAAAAAHHH''. She tried to hide her head under a cushion but i grabbed her hair and pulled her head back so i coul d control the depth of my penetration. she loved that even more . i came instantly. we both just sort of layed there i th9nk surprised by the passion of what we had done. i have never known a woman like her. and trust me i have looked long and hard. and her shoes were always an integral part of our sex. get the right woman into the right pair of shoes and hey presto. i had stopped looking for a new partner but remembering these times i will have to start searching again before i get too old
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qazwsxedcrfv
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Re: 1st time shoes and sex with a female

Post by qazwsxedcrfv »

Don't know if this counts because shoes weren't specifically involved in the sex, but this was the first time I had sex with a girl while she kept her shoes on. It happened in college, so 10 years ago or more. I was out with friends, and this one girl in our group offered to take me home afterwards (we lived near each other). We'd known each other for 3 or 4 years at this point and had never fooled around, plus she had a boyfriend at the time so I wasn't expecting what happened next. (Not that it makes it any better, but dude was super weird and creepy and they didn't last long anyway.) Also, this girl was way out of my league in the looks department, so not sure what happened. Anyway, that whole night while we were out she kept dancing with me, but it was less dancing and more her just grinding on my dick, which was rock hard at this point. She was going to town both with her ass and crotch to crotch. I was really, really drunk so I didn't even think about her boyfriend or why she was humping me. I just let it happen. Anyway, the night continues and she takes me home. I don't remember a whole lot of what happened that night because I was really drunk, but I do remember her on top of me, both of us still clothed but with our pants open. She was incredibly religious (Catholic) and against using condoms, but apparently still ok with having sex. I don't think she stuck my dick inside her, either because she thought that sex without penetration was ok or because of the whole "no condom" thing, but I also don't remember much so I'm not sure what all she did. I just remember her humping my brains out with her vagina rubbing against my dick. I also remember waking up later after she'd left with my underwear, pants, and bed soaked in cum, so she must have made me cum on her multiple times. She kept her boots on the entire time, but I don't think she knew about my fetish or made a conscious decision to wear them during sex. I think she just didn't bother taking them off since she kept her other clothes on too. Since I don't remember much of what happened that night, I'd like to think that maybe she also gave me a bootjob or sucked my dick while wearing her boots. Or that with as many times as she made me cum that some of my jizz ended up on her boots. Even if it was just the humping with her boots on, it was incredibly hot and I still masturbate thinking about it to this day. Attached are some pictures of her wearing those boots.
fucking in boots.png
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jonno1066
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Re: 1st time shoes and sex with a female

Post by jonno1066 »

qazwsxedcrfv wrote: Sat Apr 23, 2022 3:14 pm Don't know if this counts because shoes weren't specifically involved in the sex, but this was the first time I had sex with a girl while she kept her shoes on. It happened in college, so 10 years ago or more. I was out with friends, and this one girl in our group offered to take me home afterwards (we lived near each other). We'd known each other for 3 or 4 years at this point and had never fooled around, plus she had a boyfriend at the time so I wasn't expecting what happened next. (Not that it makes it any better, but dude was super weird and creepy and they didn't last long anyway.) Also, this girl was way out of my league in the looks department, so not sure what happened. Anyway, that whole night while we were out she kept dancing with me, but it was less dancing and more her just grinding on my dick, which was rock hard at this point. She was going to town both with her ass and crotch to crotch. I was really, really drunk so I didn't even think about her boyfriend or why she was humping me. I just let it happen. Anyway, the night continues and she takes me home. I don't remember a whole lot of what happened that night because I was really drunk, but I do remember her on top of me, both of us still clothed but with our pants open. She was incredibly religious (Catholic) and against using condoms, but apparently still ok with having sex. I don't think she stuck my dick inside her, either because she thought that sex without penetration was ok or because of the whole "no condom" thing, but I also don't remember much so I'm not sure what all she did. I just remember her humping my brains out with her vagina rubbing against my dick. I also remember waking up later after she'd left with my underwear, pants, and bed soaked in cum, so she must have made me cum on her multiple times. She kept her boots on the entire time, but I don't think she knew about my fetish or made a conscious decision to wear them during sex. I think she just didn't bother taking them off since she kept her other clothes on too. Since I don't remember much of what happened that night, I'd like to think that maybe she also gave me a bootjob or sucked my dick while wearing her boots. Or that with as many times as she made me cum that some of my jizz ended up on her boots. Even if it was just the humping with her boots on, it was incredibly hot and I still masturbate thinking about it to this day. Attached are some pictures of her wearing those boots.
fucking in boots.png
Mega cool boots and story. What size did she wear?
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qazwsxedcrfv
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Re: 1st time shoes and sex with a female

Post by qazwsxedcrfv »

8.5 US. I had no idea but was able to find some pictures I took while cumming on some of her other shoes where you can see the size label.
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