When I experienced anal sex for the first time with a teacher
- 1 year ago
- 18
- 0
Journey01: free porn video
Suppose my fascination is about lingerie and femininity - ever since I sneaked my mum's Penthouse magazine stash for a quick daily rub (before I knew of masturbation let alone how to perform it !) the attraction of pubic hair peeking from lacy underwear just got my immediate and lustful attention.
Then the stories slowly started to interest me just as much and these nurtured my imagination - especially the lesbian ones. I imagined being not really been involved with myself in a threesome with two bisexual girls but more me being a girl...a wanton woman, a horny pubescent slut! I then started rummaging through my mum's knicker drawer - a plethora of lacy black panties, bikini style quick snap, pantyhose and bra's. If I ever knew I'd have at least an hour of the house to myself....I'd be either on my parents bed (mum's side) or on my bedroom floor with a few chosen mags and me appropriately attired with a pair of my mum's panties, lacy bra (stuffed with stockings/pantyhose to fill the 36C cup), wig and maybe a skirt or floaty dress...fucking (i.e. rubbing myself) against those Penthouse girls.
Later, during the school holiday's, I'd even put on lipstick and/or bound myself up (I had 'acquired' some bondage magazines whilst at the barbers and was rather lithe/agile) with pantyhose or my sisters ribbons. Dressed like a bund tart with ankles trussed, wrists behind my back and a pair or two of mum's dirty lacy knockers in my mouth. This submissive scenario soon progressed to golden showers and me relieving myself in a different way but getting the same exhilaration and euphoria!
Then during a few of these sessions I would sense my anus tingling and needing attention. I soon imagined being bound and being forced to suck cock. Then my dressed wanking (I had progressed to wanking by now....mid-teens) would include me sucking my own cock. I'm average in size and length but would flick my knees and bend to gobble my head and swallow my warm cum. Later when nightclub nights ended with no quick cunt feel or fuck, I'd just, feeling all relaxed and tipsy, bend and plop my cock into my mouth...rocking/bobbing away until I came.
Still enjoying dressing up, I started to visit the sex shops and would purchase crotchless lingerie as well as a dildo or two. I then would purchase CD/Tranny mags and watch BiSex/SheMale VHS videos. The desire for cock was becoming more....desperate. I had my fair share or girls, ladies, woman up to this stage but entering my post teen years there was always something that made me instantly aroused....cocks in a frock!
This is where my story really begins. NZ 80's and early 90's
My mates and I would head into town and partake in all that was great. We enjoyed the nightlife of all the fashionable bars and clubs and all got our fair share - if you were into vanilla sex. Then there was a particular club that became our go to club as many of the 'lovely' people would stop by on their way to the next wannabe bar. It had a great atmosphere, good music and beautiful people....it was also a cabaret venue that put on a tranny show.
Intermingled were your, now termed, LBGT community and damn it was good down there. My attention was always drawn to the TV's (I'll generalise here so please excuse, no offense intended) who chatted, danced and sashayed down there. They were either glammed up, demure or downright stunningly gorgeous. There was one who pretty much every male took a second glance or said if there was ever one time...they would. That was Melissa - think Cindy Crawford but with a cock! She was also one of the performers - the star really. Well, my little secret was not really acted upon down there even though the temptation was so so near. Anyway, I had that cad-type reputation so didn't act on my impulses especially as we were still a bunch of mates all visiting (not as often as the years passed by). Then....
One night, just the two of us just popped down. The club was quiet, it was early, but we were stoked up a bit and out to have some fun - drink, dance and pickup a one-nighter. Steve decided to get a drink at the second bar in the venue and said "...let's chat with.." the TV's that were hanging out there....it was also darker in this corner of the club. There were around six of them - couple new ones I hadn't recognised (later found out there just streetwalkers) and Melissa. Melissa and a blond TV (name escapes me) were sat on stools together chatting and sipping their drinks from a straw - exchanging fashion comments I think. Steve manoeuvred to one side as he wanted to chat with the bleach blond TV (statuesque with perky tits and gold hot pant outfit). I decided to just keep quiet and stand behind Melissa's stool for a bit - unsure of who was watching. Melissa was wearing a deep cut blue satin dress with a centre slit from hem to mid-thigh and was looking as stunning as ever. When I realised that it was probably going to be quiet for the entire evening....I made a move. I delicately started massaging Melissa's exposed back. She didn't move/flinch - just peered over her shoulder and gave a Cheshire grin with the straw to her glossed full lips. I feathered, stroked, kneaded and palmed that back and shoulders lovingly. I glanced over at Steve and he was more engaged - he was snogging his blond TV! Anyway, I didn't want jump too soon and wished to savour Melissa's warmth. She exhaled and stood in front of me...I held her womanly hip and guided her towards me - we were snug. I was now massaging her shoulders and back with one hand other was making its move from Melissa's firm buttocks. Kneading that bum soon resulted in me tickling/teasing her rear crack (skirt had risen a bit!). Melissa pushed against me. It was starting to g to the next level. My top massaging hand moved to her delectable neck and then offered Melissa's mouth a finger. She teased it with a flick of her pink tongue but wouldn't suck it there. Meanwhile, my bottom hand soon found its heaven....Melissa's knickers. I slowly ran my fingers along the gusset seam, pulling snapping her dainty panties. A little flinch was Melissa's reaction but her grinding was now more pronounced (the beating music helped disguise our play). I wanted to massage her manhole so edged my way but....her cock head was there. Now this was the first time in my life I had rubbed another cock!. My mind and heart went BOMM! I slowly started to stroke along her tucked clit dreamingly.
Then, Melissa turned and looked at me. She starred deeply into my eyes and I knew she wanted me then and there. She grabbed my hand ad started to lead me. I looked around and Steve, and all the other girls (TV's et al) was watching us. He asked where we were going? I said I dunno....and let Melissa lead me across the dance floor to the stage and the back changing rooms. Once in there she locked the door. We just went for it...kissing passionately, deeply. Inhaling each others lust and nibbling, biting flesh. I just grabbed the back of her head and thrust my tongue into that sumptuous mouth - she responded in devouring kind. Melissa is about 2-3 inches taller than me in flats but I was sooo aroused I just wrapped my arms around her thighs and bottom and lifted her high against that door...she squealed like a girl. I then lifted her again onto my shoulders so her thighs were wrapped around my neck...man she had a grip on me and was soon undulating against the door. She snaked a hand between her legs and freed her manly soft thick clit. It was now millimetres from my mouth and nose. This is the closest I have been to another mans cock and I could smell its muskiness, I could see her pubic hair at the base of her penis (thankfully she didn't fully shave)....it was intoxicating! I went for it - I gobbled that beautiful shemale cock and thought to myself what a fucking lucky guy that my first cocksucking session belonged to a truly stunning shemale. I managed to engineer one hand and knuckle knead her boy pussy - probing, twisting her anal softness. I teased the under of her cock, I licked along, I licked around, I let my juicy luscious lips kiss that warm shecock till Melissa was begging to be put down.
Melissa was getting raunchy now and wanted to taste me. I quickly stripped as did she and we stood there naked in this backstage changing room taking a hedonistic moment to admire each other. She knelt on her fallen dress and held my now aching cock. I tweaked my hard nipples as she sucked and teased. Knock, thump thump! It was Steve, asking if I was okay. "Yeah...everything's good mate! I'll be out soon, Melissa's just showing me some of her outfits" was all I could think of in reply All the while, Melissa was sucking my cock and balls whilst fiddling with her clit. I said to Melissa, I want to suck your cock as it's my first and I'm in love with it. She was taken aback because she said it felt like I was a pro...so must be born for it! Now, this meant both her cock but more pertinently...I like to suck cocks - I'm incocksicated with sucking penis!
Melissa lay down and I just kissed, rubbed, brushed and licked my way her heaven-like body for the next....but when I got to her anus - gentle me went out that door. I just lifted her cheeks of the floor and demanded she pull her knees up. He puckered rosebud was there for me. Throbbing, glistening almost beckoning me to eat. Choice word 'eat' as that's what I did. I then flat-fat tongued from spine tail to perineum (area between anus and vagina/scrotum). I wuld then stiff tongue dart/lick the same bodily path. Each occasion meandering around the rosebud. I then started to probe Melissa's boy pussy with my tongue- deep, wriggling, lapping - she was squirming, I was in heaven! I moved one hand to wank her clit whilst I prised open one of her arse cheeks with my face - tongue still darting, head still bobbing. The smell of her balls and that sweet arse...dreamy! I spat on my free hand and spread more of my saliva on her anus and my fingers. Her rosebud was now almost slurpy soft, she was relaxed. So I inserted one finger and as I did nibbled her balls (one knee now supporting her bottom exposed coiled position) started to gently stroke in and out - every now and again spitting for lubrication. As the club music could easily be heard, I was using its beat/tempo as a guide and one particular tune fated at the most opportune time - I still use that tune when performing the same anus probing/stroking act and get the same orgasmic result each time. Now I was slightly alongside Melissa. As I was rhythmically thrusting with (now) two fingers and sucking Melissa's stiff cock at the same time, Melissa reached round and jammed a finger up my bum hole. I pushed against it - it hurt a bit as I wasn't lubbed but the initial pain of it subsided once her other hand started to pinch/tease my nipple. I then quickly alternated between sucking Melissa's hard cock and kissing her delicious mouth/lips as I could sense she wasn't far from coming with the abrupt hip thrusts and moaning. Then bammm! I was rewarded with another first...another mans warm delicious cum! I didn't let a drop escape my lapping and we hard kissed and groped until her orgasm had fully subsided. I re-positioned to her manpussy and ate away at her softness. She asked if I wanted to cum but I told her I was more than satisfied and thanked her for a truly memorable first time experience. We kissed and touched getting dressed and I had one last suck of her cock before she unlocked the door and we partied into the night.
The following weeks I experienced more TV sessions (primarily those other five as word got around) and honed my cock sucking and rimming for the next few years in NZ. More experiences to come...especially re: those when I moved to London.
Then the stories slowly started to interest me just as much and these nurtured my imagination - especially the lesbian ones. I imagined being not really been involved with myself in a threesome with two bisexual girls but more me being a girl...a wanton woman, a horny pubescent slut! I then started rummaging through my mum's knicker drawer - a plethora of lacy black panties, bikini style quick snap, pantyhose and bra's. If I ever knew I'd have at least an hour of the house to myself....I'd be either on my parents bed (mum's side) or on my bedroom floor with a few chosen mags and me appropriately attired with a pair of my mum's panties, lacy bra (stuffed with stockings/pantyhose to fill the 36C cup), wig and maybe a skirt or floaty dress...fucking (i.e. rubbing myself) against those Penthouse girls.
Later, during the school holiday's, I'd even put on lipstick and/or bound myself up (I had 'acquired' some bondage magazines whilst at the barbers and was rather lithe/agile) with pantyhose or my sisters ribbons. Dressed like a bund tart with ankles trussed, wrists behind my back and a pair or two of mum's dirty lacy knockers in my mouth. This submissive scenario soon progressed to golden showers and me relieving myself in a different way but getting the same exhilaration and euphoria!
Then during a few of these sessions I would sense my anus tingling and needing attention. I soon imagined being bound and being forced to suck cock. Then my dressed wanking (I had progressed to wanking by now....mid-teens) would include me sucking my own cock. I'm average in size and length but would flick my knees and bend to gobble my head and swallow my warm cum. Later when nightclub nights ended with no quick cunt feel or fuck, I'd just, feeling all relaxed and tipsy, bend and plop my cock into my mouth...rocking/bobbing away until I came.
Still enjoying dressing up, I started to visit the sex shops and would purchase crotchless lingerie as well as a dildo or two. I then would purchase CD/Tranny mags and watch BiSex/SheMale VHS videos. The desire for cock was becoming more....desperate. I had my fair share or girls, ladies, woman up to this stage but entering my post teen years there was always something that made me instantly aroused....cocks in a frock!
This is where my story really begins. NZ 80's and early 90's
My mates and I would head into town and partake in all that was great. We enjoyed the nightlife of all the fashionable bars and clubs and all got our fair share - if you were into vanilla sex. Then there was a particular club that became our go to club as many of the 'lovely' people would stop by on their way to the next wannabe bar. It had a great atmosphere, good music and beautiful people....it was also a cabaret venue that put on a tranny show.
Intermingled were your, now termed, LBGT community and damn it was good down there. My attention was always drawn to the TV's (I'll generalise here so please excuse, no offense intended) who chatted, danced and sashayed down there. They were either glammed up, demure or downright stunningly gorgeous. There was one who pretty much every male took a second glance or said if there was ever one time...they would. That was Melissa - think Cindy Crawford but with a cock! She was also one of the performers - the star really. Well, my little secret was not really acted upon down there even though the temptation was so so near. Anyway, I had that cad-type reputation so didn't act on my impulses especially as we were still a bunch of mates all visiting (not as often as the years passed by). Then....
One night, just the two of us just popped down. The club was quiet, it was early, but we were stoked up a bit and out to have some fun - drink, dance and pickup a one-nighter. Steve decided to get a drink at the second bar in the venue and said "...let's chat with.." the TV's that were hanging out there....it was also darker in this corner of the club. There were around six of them - couple new ones I hadn't recognised (later found out there just streetwalkers) and Melissa. Melissa and a blond TV (name escapes me) were sat on stools together chatting and sipping their drinks from a straw - exchanging fashion comments I think. Steve manoeuvred to one side as he wanted to chat with the bleach blond TV (statuesque with perky tits and gold hot pant outfit). I decided to just keep quiet and stand behind Melissa's stool for a bit - unsure of who was watching. Melissa was wearing a deep cut blue satin dress with a centre slit from hem to mid-thigh and was looking as stunning as ever. When I realised that it was probably going to be quiet for the entire evening....I made a move. I delicately started massaging Melissa's exposed back. She didn't move/flinch - just peered over her shoulder and gave a Cheshire grin with the straw to her glossed full lips. I feathered, stroked, kneaded and palmed that back and shoulders lovingly. I glanced over at Steve and he was more engaged - he was snogging his blond TV! Anyway, I didn't want jump too soon and wished to savour Melissa's warmth. She exhaled and stood in front of me...I held her womanly hip and guided her towards me - we were snug. I was now massaging her shoulders and back with one hand other was making its move from Melissa's firm buttocks. Kneading that bum soon resulted in me tickling/teasing her rear crack (skirt had risen a bit!). Melissa pushed against me. It was starting to g to the next level. My top massaging hand moved to her delectable neck and then offered Melissa's mouth a finger. She teased it with a flick of her pink tongue but wouldn't suck it there. Meanwhile, my bottom hand soon found its heaven....Melissa's knickers. I slowly ran my fingers along the gusset seam, pulling snapping her dainty panties. A little flinch was Melissa's reaction but her grinding was now more pronounced (the beating music helped disguise our play). I wanted to massage her manhole so edged my way but....her cock head was there. Now this was the first time in my life I had rubbed another cock!. My mind and heart went BOMM! I slowly started to stroke along her tucked clit dreamingly.
Then, Melissa turned and looked at me. She starred deeply into my eyes and I knew she wanted me then and there. She grabbed my hand ad started to lead me. I looked around and Steve, and all the other girls (TV's et al) was watching us. He asked where we were going? I said I dunno....and let Melissa lead me across the dance floor to the stage and the back changing rooms. Once in there she locked the door. We just went for it...kissing passionately, deeply. Inhaling each others lust and nibbling, biting flesh. I just grabbed the back of her head and thrust my tongue into that sumptuous mouth - she responded in devouring kind. Melissa is about 2-3 inches taller than me in flats but I was sooo aroused I just wrapped my arms around her thighs and bottom and lifted her high against that door...she squealed like a girl. I then lifted her again onto my shoulders so her thighs were wrapped around my neck...man she had a grip on me and was soon undulating against the door. She snaked a hand between her legs and freed her manly soft thick clit. It was now millimetres from my mouth and nose. This is the closest I have been to another mans cock and I could smell its muskiness, I could see her pubic hair at the base of her penis (thankfully she didn't fully shave)....it was intoxicating! I went for it - I gobbled that beautiful shemale cock and thought to myself what a fucking lucky guy that my first cocksucking session belonged to a truly stunning shemale. I managed to engineer one hand and knuckle knead her boy pussy - probing, twisting her anal softness. I teased the under of her cock, I licked along, I licked around, I let my juicy luscious lips kiss that warm shecock till Melissa was begging to be put down.
Melissa was getting raunchy now and wanted to taste me. I quickly stripped as did she and we stood there naked in this backstage changing room taking a hedonistic moment to admire each other. She knelt on her fallen dress and held my now aching cock. I tweaked my hard nipples as she sucked and teased. Knock, thump thump! It was Steve, asking if I was okay. "Yeah...everything's good mate! I'll be out soon, Melissa's just showing me some of her outfits" was all I could think of in reply All the while, Melissa was sucking my cock and balls whilst fiddling with her clit. I said to Melissa, I want to suck your cock as it's my first and I'm in love with it. She was taken aback because she said it felt like I was a pro...so must be born for it! Now, this meant both her cock but more pertinently...I like to suck cocks - I'm incocksicated with sucking penis!
Melissa lay down and I just kissed, rubbed, brushed and licked my way her heaven-like body for the next....but when I got to her anus - gentle me went out that door. I just lifted her cheeks of the floor and demanded she pull her knees up. He puckered rosebud was there for me. Throbbing, glistening almost beckoning me to eat. Choice word 'eat' as that's what I did. I then flat-fat tongued from spine tail to perineum (area between anus and vagina/scrotum). I wuld then stiff tongue dart/lick the same bodily path. Each occasion meandering around the rosebud. I then started to probe Melissa's boy pussy with my tongue- deep, wriggling, lapping - she was squirming, I was in heaven! I moved one hand to wank her clit whilst I prised open one of her arse cheeks with my face - tongue still darting, head still bobbing. The smell of her balls and that sweet arse...dreamy! I spat on my free hand and spread more of my saliva on her anus and my fingers. Her rosebud was now almost slurpy soft, she was relaxed. So I inserted one finger and as I did nibbled her balls (one knee now supporting her bottom exposed coiled position) started to gently stroke in and out - every now and again spitting for lubrication. As the club music could easily be heard, I was using its beat/tempo as a guide and one particular tune fated at the most opportune time - I still use that tune when performing the same anus probing/stroking act and get the same orgasmic result each time. Now I was slightly alongside Melissa. As I was rhythmically thrusting with (now) two fingers and sucking Melissa's stiff cock at the same time, Melissa reached round and jammed a finger up my bum hole. I pushed against it - it hurt a bit as I wasn't lubbed but the initial pain of it subsided once her other hand started to pinch/tease my nipple. I then quickly alternated between sucking Melissa's hard cock and kissing her delicious mouth/lips as I could sense she wasn't far from coming with the abrupt hip thrusts and moaning. Then bammm! I was rewarded with another first...another mans warm delicious cum! I didn't let a drop escape my lapping and we hard kissed and groped until her orgasm had fully subsided. I re-positioned to her manpussy and ate away at her softness. She asked if I wanted to cum but I told her I was more than satisfied and thanked her for a truly memorable first time experience. We kissed and touched getting dressed and I had one last suck of her cock before she unlocked the door and we partied into the night.
The following weeks I experienced more TV sessions (primarily those other five as word got around) and honed my cock sucking and rimming for the next few years in NZ. More experiences to come...especially re: those when I moved to London.
Cayleigh
- 10.08.2022
- 19
- 0
