On Monday night I was searching the Internet for a holiday when the computer 'pinged' and a blue square popped up in the corner. Slightly surprised I read the message, "Flyboy; says Hi."
It took me a few seconds to realise what it meant.
Three months previously, just before had gone to University my daughter had set up an MSN messaging account for me to keep in contact with her and her sister in Spain.
'Hi. Do I know you?' I replied to the stranger.
'No...but I love your name. Do you look like her?' The stranger instantly replied.
I instantly blushed like a tomato.
'Oh.....thanks......sort of.' I typed.
'Really? Do tell.'
'That’s my nickname among my friends and family.' I replied as I turned to look at the reflection of my long legs and hour glass figure in the mirror for some sort of confirmation.
'Because?' The stranger asked again.
'When I was younger I looked a bit like her, even my hair. A friend of a boyfriend teased me -- calling me Betty Boop; then it stuck.' I smiled at the memory; then took a sip of my wine.
'why? do you look like her? Big tits and ass?'
I was shocked at his (I presumed that Flyboy was a he) language but replied for some bizarre reason.
'I suppose so; plus I've got big brown eyes and long lashes -- just like her.' I didn't mention my long legs and huge backside and boobs. I waited for the reply. It was there in seconds.
'How big are your tits then?'
I was giggling now as I read the message and took another sip of wine.
'Big enough (lol).'
I'd hardly pressed send when he replied again.
'Go on....tell me how big they are.'
I chuckled at his audacity. By nature I'm not shy and never have been; but I'm not used to guys talking to me like this; even if it was on the Web.
'Tell me who you are.......and I might.' I teased him.
'OK....I'm from the USA, 45, married, 3 kids, 6feet 1, 165lbs, short brown hair with flecks of grey and I'm a pilot.'
"Wow!" I thought, "a pilot!" Then remembered my daughter's stories about guys spinning her a line when they chatted her up.
'A pilot?????' I challenged him.
'Seriously...I am; not a glamorous one...more of a delivery man'. He went on to explain that he'd been in the US Airforce and now worked for a parcel carrier; flying to Europe twice a week and was currently in a hotel in Frankfurt . I believed him.
We chatted about ourselves for nearly an hour -- I told him that I'd been divorced for 7 years, was 41 and worked in an Estate Agents (AR Werth) in the centre of town; plus lots of meaningless stuff too. He told me about his family but admitted to 'getting lonely' while in hotels but now contented himself with chatting on Messenger. I didn't believe him.
Just before he got bored with me he asked again.... 'are you going to tell me how big your tits are? I'm going crazy here fantasising about you!!!!'
I was now onto my third glass of wine and was flattered by his persistence and flirting.
My hand was trembling as I typed; '36EE' then pressed send.
A few seconds passed then....'ping' ...his reply came onto my screen.
'Geez....they sound fantastic. I'm a big tit man......can I see them?'
The drink had fuddled my brain and I didn't really understand what he meant.
'What do you mean? How could I show you?'
'Have you got any photos?'
'Oh God no! Plus I wouldn't know how to send them.' I quickly typed.
'That's a pity' Flyboy wrote, then immediately sent another message, 'have you got a webcam?'
'Yes,' I naively replied.
I'd used it a couple of times with my daughters and still wasn't sure how to get it to work; but Flyboy talked me through which buttons to press and after a couple of false starts we could see each other. My heart was pounding as his picture flickered onto my screen. Not just because he was gorgeous but mostly because I'd learned a new computer skill.
After waving at each other and grinning like the drunken fool I was; Flyboy plied me with loads and loads of compliments which weakened my resolve just as much as the 2/3 of a bottle of wine I'd drank.
'So? Are you going to show me those gorgeous puppies?' He persisted with a twinkle in his eye.
I smiled and shrugged my shoulders. I was desperately trying to appear calm and in control but my stomach was in knots and my heart was racing so fast I thought I was going to hyper ventilate.
'Please babe' he pleaded and pouted, 'I've got such a stiffy here and I really need to jerk off before I go to sleep.'
Wow! That put my brain back into gear.
'Really?' I typed.
'Sure have. Do you want to see it?'
I had a drunken dilemma now. In the 7 years since I've been divorced I've had two boyfriends and a single one-night stand with a married man; but because all of my girlfriends were either knee deep in children or in the first flush of love in their second marriages I hadn't had the opportunity to go out 'on the pull' for nearly two years and had become a very proficient masturbator. Recently it had been 4 or 5 times a week and I was becoming perpetually horny which possibly explains why I'd so readily got involved in an online chat like this.
'OK' I replied as casually as possible. If he knew anything about women he would have realised from the look on my face and my nipples which had suddenly popped out; I was desperate to see a real cock.
Flyboy grinned and winked as he pushed his chair back. He lifted the hem of his t-shirt revealing a nice big bulge in his boxers which he lovingly caressed.
'GET ON WITH IT!' I wanted to shout.
Still with a grin on his lips he pulled his pants down to his knees and revealed a lovely thick semi-hard cock. I was mesmerized but didn't know how I was supposed to react.
'So you like it then?' He typed with his free hand as he began shaking and rubbing his cock making it grow a little bit harder.
Forgetting he could see me, my eyes were like saucers and my mouth was virtually hanging open.
'Yes.' was all I could think of to type and gave him a 'thumbs up'.
'Your turn.... now show me your tits so I can jerk off.'
This was all new to me and I wasn't thinking straight anymore. The thrill of chatting and flirting with an electronic stranger had made me even hornier than usual. Without a seconds' thought I pulled the cami-top of my pyjamas over my head leaving me in a revealing lacy white bra and pyjama bottoms.
'MMMMMMM...they look nice....squeeze them for me.' Flyboy typed.
As if hypnotised I obeyed; squeezing and stroking my large mammaries as he tugged at his cock and hairy balls making it grow fatter and longer.
'If you take your bra off I'll jerk off.... just for you.' Flyboy told me.
The opportunity to watch a nice looking guy actually wank for me was a turn on too far. The little Devil that used to sit on my shoulder in my younger wilder days made an uninvited appearance and prodded me with his pitchfork - I immediately put my hands behind my back and unhooked my bra; letting it fall forward .and exposing my big boobs
Flyboy chuckled and typed; 'Shit! Those puppies are fucking triple A!" then he began rubbing really fast.
My pulse and heart were racing as I stroked and squeezed my tits again...for him. It felt really, really naughty as I tugged at my nipples and squashed them together to turn on this absolute stranger who was masturbating on my PC screen. My boobs and nipples are very sensitive at the best of times so after a couple of minutes I was squirming on my chair and urgently needed some relief myself. Flyboy was now standing up and changing hands every few seconds in his urge to cum. Before I knew what was happening one of my hands was down the front of my pj's and rubbing my clitty.
Flyboy had obviously seen me do this and leaned forward to type; 'Take your pants off and show me what you're doing.'
Drunk, horny and delirious with an itch between my legs I obliged by slipping my pj's down to my knees then leaning back in my chair -- legs apart! Our hands were both a blur as he wanked his big cock and I rubbed and fingered myself on screen for each other. Less than a minute after showing him my hairy kitty he was shooting cum all over the hotel desk. This tipped me over the edge and I came to an abrupt screaming orgasm by jamming three fingers into my hole as I furiously rubbed my stiff clitoris with the palm of my hand.
Flyboy stumbled backwards and grabbed hold of the chair to steady himself. I was leaning backwards gasping for air with my legs still spread when he began typing.
'Did you enjoy that?'
I chuckled and typed, 'What did it look like?'
W flirted for another minute or two then he made his excuses and logged off. All alone and naked in my living room the enormity of what I'd just done hit me like a lead weight and I began to sniffle and a tear or two ran down my cheek. Embarrassed; I pulled my pyjama bottoms up and clutched my bra and cami-top in front of me. I swiftly logged off and made my way to the bathroom. As I wiped between my legs I slowly stopped feeling guilty and the little Devil on my shoulder took charge again. It had actually been fun; lots of fun.....and I had that itch again between my legs.
Once in bed and under the duvet I fumbled in my knickers drawer until I found 'old faithful' -- my six inch plastic vibrator. It had seen me through many a lonely night and tonight would be the same. My kitty was still soaking and the hard plastic slid in with ease. 'Mmmmmm' I purred as I re-lived the webcam show and switched the toy on. The sex toy was so old it sounded and felt like a traction engine but that was just what I needed because of the mood I was in -- horny and dirty. Normally I would slowly build up the strokes but now all I needed was a good hard fucking and that's what I gave myself; eventually flicking my clit in time until I had another back-arching orgasm.
"What a night!" I chuckled as I fell into a deep sleep.
I was in such a good mood the following day at work; my boss even commented on it. Little did he know why I was smiling!
As soon as I arrived home I switched the computer on and immediately opened MSN. Ping-ping-ping! There was nothing from Flyboy but there were 8 messages from strangers who wanted to be added as 'my friend'.
Two of them told me that Flyboy had told them that Betty Boop likes 'to play' and they should contact me. The rotter had 'kissed and told' about our fun. I was both angry and flattered that he'd enjoyed himself so much that he was now 'showing me off' and sharing me with his online buddies. I agreed to be 'their friend’, answered some e-mails then heated up a boring meal for one.
I was just finishing my lasagne when I heard the familiar 'ping'. again At first I thought that it may be one of my daughters; but the message read 'Uncle Monty wants to play -- are you feeling frisky?'
"Oh my God!" I nearly panicked as I recognised the name from the earlier 'friend' requests.
'Hi.' I replied.
'Feeling frisky?' Uncle Monty asked.
'Not yet' I typed.
We chatted for a few minutes but he was a bit 'full on' with no subtlety. If I was to repeat the goings on of the previous evening at least I wanted to be treat like a lady!
Monty soon lost interest but was replaced by Cheshire Cat who was much nicer. By the time he asked to go on webcam to play he'd got me tell him about the previous evening, losing my virginity, my first blow-job and what underwear I had on. He was disappointed that I was wearing tights and not stockings under my skirt but cheered up when I told him that I did occasionally wear stockings and hold ups.
When we went on cam Cheshire Cat was very complimentary just like Flyboy had been (I soon realised that this was a ploy guys would use to break down my inhibitions -- how naive was I?).
This guy was British and a lot older than Flyboy; probably in his 60's with grey hair, twinkling eyes and a bushy moustache.
As I sipped my wine he told me about his love of stockings and told me a couple of stories about other women that he chatted too on MSN. I was surprised at how many people did what I'd done the previous night on a regular basis. The sheer excitement of this new experience was making my heart race and my kitty itch like mad. I couldn't wait to strip off just like the previous night.
Eventually he told me that he was getting turned on and 'did I want to see his cock?' I nodded and typed 'yes please'. (Always courteous).
It wasn't as big as Flyboy's cock but nice and stiff all the same.
"Can I see your tits now?' he politely asked. I obliged by slowly unbuttoning my blouse and revealing my bra. He was wanking so fast I was worried that he would cum before I'd got them out. Just as I was unclipping my bra 'ping-ping'; another two 'friends' wanted to watch my cam. I immediately pressed agree. I couldn't stop grinning as I shook my big tits free of my bra knowing three horny guys were now watching me and pulling on their cocks.
Without being asked I started caressing and stroking my tits and ever stiffening nipples until Cheshire Cat told me to suck them. Without a second thought I complied and for the first time in my life I lifted a teat up to my mouth licked my own nipple then suckled on it as I dug my fingers and long red fingernails into the other one. It only took a minute for Cat to spurt cum onto his keypad. I felt like a right dirty minx as the others started sending crude messages too as they tugged their cocks on webcam for me.
By the time my skirt and tights were around my ankles Cheshire Cat had gone but had been replaced by another 3 'friends'. I was shaking with lust and excitement as two guys simultaneously told me to take my knickers off. I was so turned on and wet the gusset was actually sticking to my quim and I had to peel it off much to their amusement.
They soon had me sitting with my legs apart, shoes back on but with the heels resting against the computer desk as I pulled my labia apart and stretching it for their pleasure. Thankfully one of them finally told me to finger myself. I kept my flaps spread with the fingers from my left hand as I dipped two fingers from the other deep in my honey pot. I now had 5 small screens up on my computer with 4 guys wanking on them - the other was me fingering my hairy pussy. I was in sexual Heaven.
'Have you got a dildo?' Someone typed.
'Yes' I answered.
'Get it and fuck yourself for me'.
Without any hesitation I stood up and walked out of the living room hoping that my sexy wiggle was still being filmed. When I got into my bedroom I froze when I realised that the curtains were open and I was naked. 'Sod it!' I thought and shimmied across the small room. With straight legs and making sure that my big tits were on view to anyone lucky enough to be looking in the window I found my vibe, and then turned to face the window. My pulse was in overdrive now and I could feel my juices running down my thighs as I returned to the living room.
Everyone was still there plus 3 others waiting to join us. Of course I accepted their requests.
With a guy called Hot Dog dictating proceedings I did as I was told by resting my high heels against the computer desk and fucked myself with my vibe as I played with and sucked my tits. I was buzzing as hard as my vibe but for some reason I was never in danger of cumming myself; not even when guys were spurting all over my computer screen. I kept on with my 'show' -- vibe in my pussy/vibe in my mouth/fingers in my pussy/fingers in my mouth/sucking my tits/slapping my tits; the show lasted nearly an hour and I was exhausted as the last two guys came and logged off.
As soon as I logged off too I pressed my vibrator against my clit and had a super orgasm all by myself; then another one and another one!
The rest of the week was much the same; I couldn't wait to get home from work and log onto MSN then put on two or three sexy shows for my new friends from across the Globe.
After work on the Friday evening I had to go to the Supermarket for my weekly shopping. I rushed around madly throwing things in the trolley in my haste to get home and rip my knickers off and get online. The only time I slowed down was to buy some new hold-up stockings as I'd had many requests during my shows for me to wear stockings from my new friends/fans.
I tried to take my time as I put the shopping away and eat the Big Mac and fries that I'd bought; but the urge to expose myself again on my webcam was taking over my every thought.
I closed the living-room blinds then lifted my works skirt and removed my tights as I checked my e-mails. When the boring things were done I selected a pair of 10 denier black hold-ups and pulled them up my long legs with trembling fingers. It felt really sexy wearing stockings under my works' uniform.
I opened a bottle of wine and poured out a large glass then logged on. Four of my 'regulars' were already waiting for me and there were another 7 requests to be my 'friend'. I clicked on 'agree' and two of them instantly joined the conversation.
My computer screen lit up with 6 smaller screens featuring guys of all shapes and persuasions salivating at the thought of watching me put on 'one of my shows' as someone had christened them. I put everyone onto conference mode and began chatting.
Questions about my working day; lateness at logging on and my 'mood' were being fired at me like machine gun bullets. I answered everyone as quickly and politely as possible; then BoingBoingBaggie asked, 'what colour panties are you wearing?'
'Black......G-String' I replied.
'Matching bra?' Dancehallcrasher enquired.
'Can I see them?' BoingBoingBaggie asked with a wink and thumbs up sign.
'Who else would like to see my undies?' I teased.
'Me me me me' came the replies. As usual my heart was racing as I stood up and moved the chair, then positioned the webcam so my viewers got a good view of my striptease.
The uniform jacket and skirt that I wore at the Estate Agents made me look a bit like a secretary which went down well with my regulars. I removed my short black jacket and company scarf then slowly unbuttoned my silver blouse until they got a glimpse of my cleavage pouring out of my lacy bra. Trying to add some mystery to my actions I turned away from the camera when I got rid of the blouse. They all had their cocks on display when I turned around. As a little treat I jiggled my boobs until they nearly pooped out. Then with a sexy roll of my hips I slowly unzipped my skirt.
Messages were flooding in but I was unable to answer any individuals but seductively lent forward until my chest pretty much filled the viewfinder and typed, 'Guess what I'm wearing tonight.'
As guesses came flooding in I eased out of the pencil skirt revealing my black and white see-thru polka dot g-string and lace top hold-up stockings. The looks on all of their faces were exactly what I'd hoped and dreamed of. I stood away from the camera with my hands on my generous hips and let them look at me (which sounds very vain).
The requests and commands soon lit up the screen; but I ignored them and just did my own thing. My eyes were fixed on all of the hard cocks that were being stroked in the screens on my computer as I danced and jiggled my tits and arse; touching my toes so they could get a good look at my tits or arse depending on my angle. After 5 or 6 minutes I couldn't wait any longer and had to remove my bra. My huge melons were aching and needed a good crushing which I gave them much to the guys delight. I mashed them and squashed them and pulled and tugged at my fat pink nipples.
My breathing was getting shorter and shallower and I couldn't stop myself now even if I'd wanted to -- I was hooked. I turned away from the camera again and pulled my knickers down and stepped out of them then flicked them with the point of my shoe across the room.
I placed one hand discretely across my hairy kitty and my arm across my chest as I turned to face the webcam. With my best Betty Boop 'look' I pressed my finger to my lips and pretended to look shocked that all of these masturbating men could seem naked but for a pair of shiny black stockings and patent leather high-heels.
The messages shot onto the screen; 'Get your tits out/show me your twat/flash your sweaty cunt'.
I loved pretending to be Betty and kept teasing them by moving my hands and not exactly showing my nipples or pubes. Then; just as a couple started to get frustrated, I let them get a good look at my tits when I picked up my wine glass; then after draining it picked up the bottle with the other hand.
A minute or so later I was back in my regular position -- sitting on my leather computer chair, legs spread wide apart, knees up to my chest, heels virtually attached to the desk and my fingers spreading my labia and showing my 'fans' how wet and pink my cunt was (as I now called it). I caressed my stocking clad legs and ran my fingers through my luxuriant pubic hair as I fingered my cunt for their masturbatory pleasure. Two guys had already shot their lot and were still wanking as I began following BoingboingBaggie's commands to finger myself. Then after 5 or 6 minutes when I'd managed to push four fingers inside my cunt someone told me to get my vibe. I was organised tonight and produced it from the desk drawer. Like lightening it was quickly buried deep inside my soaking wet cunt.
Their hands were rubbing 20 to the dozen as I fucked my cunt with the white plastic toy.
I carried on like this for a few minutes until someone told me to 'tickle the skin at the bottom'. WOW! I'd never done that before and it was very sensitive and moved my sexual sensations up a gear or two.
Then Dancehallcrasher typed, 'finger your ass.'
I froze for a second or two then instinctively slid my finger further South until it was pressing against my bum-hole. WOW and double WOW! I couldn't believe how aroused it made me as I pressed my finger tip against the puckered lips. The harder I pressed the sexier it felt and the faster I fucked myself with my toy. Then it happened more by accident than design -- I was so sloppy wet my finger slid into my bum hole by about an inch. I orgasmed immediately. A real full on breathtaking jaw dropping orgasm. I was stunned.
Splat-splat-splat. Three guys all jerked off at exactly the same time. One tattooed guy; who I'd seen do the same thing earlier in the week; managed to make his cum shoot upwards in an arc and fall in front of his webcam. The other two let theirs ooze out onto their desks.
As soon as I got my breath back I flicked the switch off on the vibe but kept sliding it up and down my greasy twat. My other finger was a different story -- I was now afraid to move it. But move it I did. Jesus H Christ it felt good as I pulled it back to the opening; then without being told what to do slid it back in, to my first knuckle at first then eventually the second. This was nowhere near as painful or as uncomfortable as I'd feared but bloody thrilling. Now virtually bent double I accidentally dropped my vibrator onto the floor and didn't want to stop so replaced it with two then three fingers in my kitty. I was soon in a self-induced daze as I stared at my image on my computer as I fingered my cunt and arse at the same time; forgetting that I was being watched by several men.
'Have you got a bigger dildo?' Dancehallcrasher asked. I shook my head.
'I want to see you really fill that cunt up. What else have you got?' He continued.
I was now so worked up I wanted exactly the same thing. With a small 'pop' I pulled my fingers out of my bum and pussy and staggered around the room in a sexual daze. Then a light bulb lit inside my brain. Of course!
I was still a bit light headed and headed into the kitchen where I opened the bag of large carrots that I'd bought earlier. Then as I turned to walk into the living room I spotted the hand of under ripe bananas that I'd also bought.
If it was possible I felt even naughtier as I waved my bounty at the webcam.
'Are these big enough?' I typed and flashed a cheeky grin at the screen.
'Which should I use first?" I giggled and asked the group.
'A banana' someone instantly replied.
'Which one?' I typed as I held the six bananas up for inspection.
'The biggest one!' was the overwhelming reply. With my heart racing like a train I pulled a banana that must have been 7 or 8 inches long and as thick as a baby’s wrist free from the rest. My mind was a blur as I resumed my position and began stroking the fruit against my wet cunt. I was actually gasping for air as I tried to slide it in. But it wouldn't go. Perhaps because it was very dry or maybe because I was too tense but I couldn't get the bloody thing inside my cunt. I was certainly wet enough but my muscles had contracted.
'Have you got any KY?' someone asked.
Only wearing my heels and the stockings I wobbled and teetered into the kitchen and grabbed a tub of hand cream -- that would have to do! Back on the chair and my black stocking covered legs as wide apart as possible and my knees retracted to my tits I smeared half of the yellow fruit in cold white cream and tried again. With hindsight I pushed too hard because all 7 or 8 inches shot inside my cunt like a missile -- taking my breath away! My eyes were bulging and my normally chubby cheeks were puffed out like Louis Armstrong! But boy did that banana feel good! It filled my hole like no man ever had.
The hard yellow fruit found places inside my vagina and stomach that I didn't know existed.....this was fantastic....in fact fucking fantastic; as I pounded my cunt with a huge banana for my sexual gratification and the pleasure of 10 guys (more had been added) on my computer.
I was puffing and panting and slapping my clitoris when someone typed, 'stick something up your arse!'
Drunk on wine and sexual adrenalin I fumbled for another banana; but even in this heightened sexual state I knew that they were going to be too big. The carrots looked perfect; long and tapered. I was about to pull the banana out when BoingBoingBaggie stopped me and insisted that I DP myself. Even with my limited knowledge of pornography I knew what he wanted me to do.
Without a thought or a care I dipped the slim end of a carrot into the pot of hand cream then with the aid of my webcam; lined it up against by puckered arse hole. This was madness; but I carried on. The cream was cold and the vegetable felt very hard as I pressed it against the tight entrance. My big brown eyes were nearly popping out of their sockets and I was puffing and panting just like in childbirth as I gave the carrot one hard push and.......whoosh......three inches or so slid up my shit-chute (as someone delightfully called it!). I was so tense my head, neck and body were as tight as a drum as I began sliding the carrot and banana as deep into my orifices as possible. My viewers were now onto their second and third wanks and no one had turned off; which I guess should have made me quite proud. My arse was on fire and my cunt was making loud squelching sounds as I began relaxing and upped the ante by twisting the phallic foodstuffs until they actually touched via the membrane separating my two passageways which gave me have a little orgasm.
After probably 5 minutes I couldn't wait any longer and pulled the carrot and banana out and thrashed at my clit until I came with a shudder and a yelp. My legs, stomach arse and kitty were all aching as I sat basking in my afterglow and the adrenalin sank down to my toes.
To a man my audience waved goodbye and some even blew kisses as they checked out. I couldn't take any more either and logged off.
The next seven weeks took the same course with me ordering three new sex toys online (including a life like 9 incher with balls and one that had a big cock for my pussy and a smaller one that fit my bum), various sets of lingerie (especially the cheap tarty stuff in nylon) and an assortment of stockings as I developed and revelled in my 'Betty Boop' online character but kept my real life quite separate. I also bought two cheap mini-dresses that made me look even more like Betty Boop when I wore them with excess make up and huge ear-rings.
Several of my regular viewers became e-buddies and we exchanged erotic and normal e-mails on a regular basis.
My online shows carried on in the same manner with me shoving something up my cunt and arse most nights. After a while I was so hooked on showing off on my webcam I had to ration myself to every other night and Sunday afternoons. It was an odd time.
I was soon a lot more confident in my 'real life' and began wearing hold-ups or stockings and suspenders most of the time at work plus I began showing a little bit more cleavage; all of which actually helped me get more house sales. Well, mostly apartments to single guys. Funny that! Sadly; because I was a professional at work and obviously never dated customers and my friends were still in relationships so I still didn't get any real sex; but I wasn't complaining.