Off the Streets

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"You look beautiful" I said. Again she caught me staring at her tits. I looked away, flustered. I picked up the bowl of pasta and placed it in the middle of the table before gesturing to the chair on the end. I pulled it out for her and was greeted with a wonderful view of cleavage as she bent to sit down.

For the next two hours I gathered a deep understanding of this fantastic woman. I listened intently as she told me her story which seemed to be a real life Cinderella fairytale. Privately educated, her mother died when she was quite young and she grew up with her stepmother with whom she had a particularly bad time. Her military father was away on duty for long periods and she had a very distant relationship with him. Things came to a head when her father hit her during a row where he refused to listen to Amy's claims of bad treatment by her stepmother. That was when she left home and she hadn't been in contact since.

Around 11pm Amy was looking tired and yawned. I'll sleep like a baby tonight" she said "I haven't slept in a proper bed for weeks, I think I'll turn in" She bent forward as she rose and again I found myself transfixed by the swell of her tits as they hung forward barely held in place by the thin halter neck of the dress. My eyes looked up from her cleavage and she was staring at me, head cocked with a smirk on her face. "It's a hypnotic dress isn't it?" she said. I felt embarrassed to be caught again. "Well this bit is anyway." She said looking down her own cleavage" As if to alleviate my embarrassment she quickly changed the subject. "Thank you for a lovely meal. You really have been so kind" She started gathering plates and crockery.

"No, leave that" I said, "I'll load it all in the dishwasher for morning." I felt as though I should take her in my arms and kiss her but almost immediately she bid me goodnight, turned and with a noticeable swaying of her hips left the room.

I tidied the kitchen and made my own way to bed. When I got to my room I stopped in the corridor, I thought I heard a whimper from the spare room. Dismissing it I went in to my room and quickly stripped for a shower. The en-suite was next to the spare bedroom and again I thought I heard someone crying. Quickly drying off I put on a pair of boxer shorts and made my way down the corridor. Stopping outside the door I heard it again, not quite a sob, more a whimper someone would make when in pain. I was torn between offering my support and leaving her to what ever private anguish she might be going through. Resigning myself to not being able to sleep if I didn't at least check on her, I tapped on the door.

"Come in" I heard her say.

I gently turned the handle and pushed the door open.

"What the fuck kept you?" she asked.

Her head cocked to one side smiling, she was sat up on the bed resting against the pillows at the far end. She was still wearing the FM dress but the halter neck tie was undone and her legs were wide apart revealing a newly trimmed pussy. In her right hand the blue dildo was being expertly worked in and out of her slippery slit whilst she managed to stroke her clit with her thumb. She stared at me as her left hand slowly pulled the fabric of the top down.

"You've been struggling to keep your eyes off my tits all evening" she said "I think it's time for your reward" Her hand dropped revealing her huge left tit, more magnificent than I even imagined. Taking her nipple between her finger and thumb she pinched, pulled and twisted it, making it harden to an inch long.

"I want to eat your cum whilst I frig myself off" she said as she increased her right hand speed. Lifting her boob to her mouth she sucked hard on the nipple, milk ran from the corner of her mouth splashing across her body. She let the tit fall and I noticed a fine spray coming from her teat. As the spray died down she looked up at me "In my mouth" she said "All over my face and tits. Wank yourself off whilst I fuck my cunt with this big fucking dildo"

I needed no second invitation; my modest cock was already straining at my boxers as I took it out and began pumping for all I was worth. She removed the dildo "Watch me" she said.

Taking the dildo out, she sucked hard on it before squeezing her nipple and spraying the head of the Rabbit with milk. Then, newly lubed from her jug juice, she held the vibrating head against her arse hole and pushed it gently into her anus. I stared transfixed, then felt her take my cock from my hand, guiding it to her mouth. Wanking me hard, she took the head and I felt the pressure of her cheeks as the suction took over. Her hand let go, reached around my back and pushed my arse forcing my cock deeper, to the hilt, before sliding back out with a loud suction plop and a stream of spit. Her hand grabbed her tit and again lifted it high, taking the nipple she sucked. Again it fell free with a loud slap and a jet of milk shot down her body over her cunt and pooled around the dildo as it was pushed deeper and deeper into her arse. She moved towards my cock and spat a mouthful of milky spit over it. Taking my hand she guided it to my cock which by now felt ready to explode.

"I'm close" she said working the dildo in her butt with her right hand whilst frantically frigging her clit with her left. "Wank yourself off over me"

I began jerking for all I was worth. Her right hand took the dildo and began giving it a blow job before shoving it deep into her now sopping wet twat. Again she lifted her tit and never losing eye contact she held it inches from her mouth, pinching the nipple and caused a jet of milk to squirt across her blood red lipstick covered lips.

"I'm coming" I grunted, as my first orgasm for a month ripped through me. A stream of cum splashed across her face, A massive load landed on her nipple. Still staring she bit down on it and I saw an emulsion of sperm and milk flood into her mouth.

"FFFFUUUUUCCCKKK! YES" she screamed as her own orgasm erupted "Agggghhhh!" Laying her head back she let go of the dildo, squeezing both tits she lay there with her mouth open as I continued pumping my spunk into her mouth.

As we both came down I stood there coming to terms with the enormity of the situation. She lay on the bed, covered in a mixture of my cum and her milk, a dildo still merrily buzzing in her pussy. She looked like every fantasy slut I had ever imagined. I suddenly felt awash with guilt.

"I'm sorry" I blurted out

"For what" she asked.

"Erm... it was, I mean, I'm sorry for being so...I mean.... it's a little degrading" I stammered.

"In that case I should apologise" she said with a frown, licking spunk from her fingers. "Women do have dirty fantasies too you know. I've always wanted to behave like a whore but never had the opportunity with a man I trusted" as she said this she lifted her cum covered tit and began licking it clean. "I new from the way you had been so kind that I could trust you, and once I saw you staring at my tits that first time we met I new that if the opportunity arose you would jump at the chance to see them and I could fulfil my fantasy"

"So" I said confused. "You're not angry?"

"Fuck no... It's the best solo fuck I've ever had and I've never watched a bloke wank himself off before. Having you come all over my tits and face was just immense...Thank you"

"Haha...Thank you" I said "I've never seen a woman suck her own tits before either, and the milk...wow "I said

"Most women can't suck their own. Whenever I've been with a man and done that he's been putty in my hands ha-ha. Want to taste it? It looks like you're ready to go again" she said nodding to my cock which had woke up again.

She sat forward and took hold of my cock. Leaning forward she placed it between her boobs, slowly moving her huge tit flesh up and down. Looking up she said "This is another fantasy of mine. You'd think a girl with tits this big had given loads of tit-wanks, and to a degree I have, but I've never done it to completion. Blokes always jump off and want to fuck me whilst sucking my tits. I want to feel your cum rise through my cleavage and splatter my neck."

I stared mesmerised as 36 inches of tit wanked my cock. Her hands whilst holding up her huge jugs were also pinching her nipples and a stream of milk was dripping from them, splashing over her thighs.

"Oh fuck" I said as my orgasm built. "Here it comes"

She clamped her tits around my cock and looking down opened her mouth again.

"Uuugh" a rope of cum shot up from her cleavage, splattering her neck and stringing out across her lips. Her tongue instinctively flicked out to lick up the salty mess. She released the grip on her boobs and lowered her head. Taking my cock in her mouth she sucked the last remnants of sperm from me and now spent, I collapsed on the bed at her feet.

"My turn" she said. Leaning back against the headboard she opened her legs and began stroking her pussy. "Lick me out" she commanded and who was I to argue.

I moved up the bed and started lapping at her clit, occasionally moving lower and darting my tongue deep into her hole. Her feet had come together and found my cock and I felt my hard on growing as she expertly started a foot wank, a truly new experience for me. She grabbed me by the sides of my head and pulled me towards her.

"Fuck me Drew" she said "Fuck me hard" and I felt her heels push my arse forward and effortlessly my cock slid home"

I began pumping away, hard like she asked. She grabbed me by the hair and pulled my face to hers. Opening my mouth I felt her tongue snake in and the taste of my own spunk filled my mouth. We snogged like newlyweds before she broke free and pushed my head towards her left tit. "Suck it Drew, drink my milk", she ordered.

I latched on and my mouth filled with warm, sweet, thin, milk I swallowed and more came. Still pumping my cock into her soaking snatch I could hear the squelching noise as it slammed home. Turning my head with her nipple still in my mouth my eyes met hers, She had her right tit lifted towards her mouth and seemed to be waiting to get my attention before sucking hard on the nipple, as it popped free, glistening and erect, she began licking it, freeing milk which ran down her body between us. I felt another orgasm rising, Letting the tit drop from my mouth I grabbed her long locks and pulled her head close. Locking mouths we began to kiss as our orgasms exploded simultaneously.

We collapsed into an exhausted sleep and when I awoke I found myself all alone. Something was bugging me, something I'd missed, I wracked my brain trying to figure out what it could be. Then I saw the envelope and one word hit home.

Drew

I had never actually told her my name. I'd told Tom my name was Andrew, but I never told her my name. All my family call me Andrew. My friends call my Andy. The only person ever to call me Drew was Alice... how didn't I notice that. Was I so comfortable in the situation that it passed me by? How did Amy know?

I picked up the envelope and read the letter.

Darling Drew.

I'm sorry I left you so soon. I came back to snap you out of your downer. When I was alive, you always treated me like a gentleman. Deep down there was always a slut bubbling away, longing to get to the surface. In death I seem to have these big mommy tits that you have just had so much fun with, maybe we get what we want in the afterlife.

You now have to move on too. I hope I have opened your mind to the adventures that life still offers you, and whilst I was at it got a chance to show you the other side of me and wear that "Fuck Me" dress once more. I can't promise that you will find another like me, but there is a perfect woman out there for you. You must go on with your life.

I will always love you my darling.

Alice.

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15 Comments
Rancher46Rancher46about 2 years ago

This story was unique and just about made me cry at end! The twist at the end as truly unexpected.

AnonymousAnonymousover 2 years ago

Was the woman pregnant like why did milk come out?

AnonymousAnonymousover 6 years ago
The Ending!

Ending is so well thought-out and heartfelt. Great job, please keep it coming!

AnonymousAnonymousabout 8 years ago

My wife died of a drug overdose several years ago . wish I could find a replacement for her --- she was the love of my life

AnonymousAnonymousover 9 years ago
wonderful

This story was unique and just about made me cry at end! Unexpected. I actually used to occasionally have sex with a very chesty woman that occasionally had bouts of homelessness.

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