Anna's release

By humpty

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Tags: Shemale, first time, anal, oral

Added: 25 Aug 2009 Views: 14858 Avg Score: 4.39

Shemale Anna finally loses her virginity and her inhibitions

Anna looked at herself in the full-length mirror, a daily ritual of self-criticism.   Her breasts had developed nicely, but without surgery they’d never be more than a small B-cup, but nonetheless, she was satisfied with what she saw.   She had grown her hair out to shoulder length, although it was quite a plain, straight, flat brown.   Anna was most pleased with her hips and bum, which with the aid of hormones and exercise, had developed nicely.   The transformation was nearly complete.   She’d soon be the woman she always knew she was born to be.   She finally removed her left hand from her groin, to reveal the part of her body she loathed above all others.   Her small, ineffectual penis.   The cause of countless jibes and insults at school, the foul thing that stopped her from fully emerging as the beautiful butterfly she had always known she could be.

To say her life had been miserable would be an understatement.   Anna’s parents (to whom she’d always been Samuel) were old-fashioned working class.   Her dad went to the club on Thursday and Friday evenings, and Sunday lunch.   Mum went along on Sunday’s too along with the other wives, allowed out for half a lager and lime as long as dinner was still cooked on time.   Dad was in the darts and snooker teams, and had played football until he turned forty.   Anna had been a disappointment to him, and he made it plain.   She’s always preferred dolls and drawing pictures to sports and other manly pursuits, and her dad could never face it.  

That combined with the constant bullying from the age of twelve, was what led her to leave home at sixteen, with nowhere to go, taking the £418 in her savings account.   On that day she stopped being Samuel, and became Anna.   She had always been called a sissy and a poof by the boys at school, and just took to wearing her big jumper and jeans, and telling anyone who asked, that her name was Anna.   Not that many people asked.   For eighteen months she had moved from pillar to post, doing odd cleaning jobs where she could.   She finally ended up in Blackpool, working in one of the seedier hotels, cash-in-hand, and made her first ever good friend.   Angie became her mentor, and treated her like a daughter, even taking her into her home, temporarily at first, but for the last four years, as her lodger.   Angie was a divorcee, and her kids had left home.   She reminded Anna of her own mum, or at least how she thought her mum could have been.

Angie was the only person who knew Anna’s secret.   She’d introduced Anna to first a counsellor, and then eventually to the doctor who had been prescribing the hormones.   She was desperately saving up for the surgery to take the final step, but it seemed an impossible target.

Anna was a virgin.   She couldn’t remember the last time she’d had an erection.   She supposed she must have as a teenager, but was fairly sure she’d never come through wanking.   Even as a teenager, she’d been excited by masturbating her anus with a variety of implements.   She’d whiled away many an afternoon fucking her arse with the handle of her hairbrush or even the loo brush.   She’d finally plucked up the courage to go into a sex shop and buy a dildo and some lubricant two years ago, at the age of 25.   She’d since become a fairly regular visitor to the adult shops of Blackpool, getting a thrill of anticipation for a couple of days before her intended visit, and usually culminating in a five or six hour session fucking her arsehole.

Anna desperately wanted a boyfriend.   She longed to cuddle up in front of the telly.   She would have loved to stroke and to lick and suck a manly cock, but the limp, pathetic thing between her own legs would put any real man off sex for life.

The following evening was Anna’s 27 th birthday, and she’d agreed to go out for a night on the town with Angie and two other girls from work.   Jenna and Sue were both in their early thirties and typical bubbly Lancashire lasses.   Anna had agreed under pressure, to a makeover and the girls turned up just after six o’clock.   Jenna had done a year on a beauty course at college when she left school, and had more makeup and hair implements than Anna had ever seen in one place before.   As Jenna produced the curlers, shimmery blusher, and fake tan, Sue produced a bottle of Vodka and cartons of orange juice.   Anna hardly ever touched alcohol, and soon began to feel a little woozy.   Jenna jumped up about an hour later.   “All done, and not a bad job if I do say so myself” Jenna said.

Anna stood, and turned to look in the mirror.   She started to fall and Sue grabbed her.   “You alright doll?” she asked with more than a little concern.

Anna began to sob.   “I look beautiful” she cried between hitches.

“Course you do you daft tart,” replied Jenna, “I did it didn’t I?”

The girls collapsed in fits of giggles and fell into a group hug.   “Now let’s get our gorgeous arses into town, and show the lads of Blackpool what they’re missing” Jenna said.

Twenty minutes later, the girls climbed from the taxi in front of a club.   “Come on girls, the last one to get a snog pays for the taxi home” said Sue, hitching her already short skirt up her legs as she climbed the steps.

Much of the night passed in a blur for Anna, in a kaleidoscope of lights, music, booze, and raucous laughter.   She began to feel a little sick, and so went outside with Angie for some fresh air, whilst Angie had a fag.   As they stood outside giggling, they girls were approached by a fit looking guy.

“Hiya Glen, what are you doing out?” asked Angie.

“Hello Ange, I’ve been out with some of the lads on a stag do.   They’ve gone onto a strip club, but it’s not my scene really.   Who’s your pretty friend?” he asked.

“Glen, Anna, Anna, Glen” said Angie.   “Glen’s an old friend, and one of the nice guys” she smiled.

“I’m thinking of getting some food, do you fancy some?” Glen asked.

“Not for me” said Angie.   “What about you Anna?”

“I think I could do with something to soak up the booze” Anna slurred.

“You gonna take care of her big boy?” Angie asked.   “You can get her home can’t you Glen?”

“Sure, if you’re OK with that Anna?”

“Done then” said Angie, before Anna had a chance to answer.   “You crazy kids have a fun night.   I’m going inside before I freeze my nipples off”

Glen and Anna settled on pizza, and headed off towards a take-away between the club and Anna’s home.   It had started to get chilly, and Glen threw an arm over Anna’s shoulder, to help warm her up.   Anna started to enjoy the contact, and then the worries began to creep in.   Glen however wouldn’t let her get a word in edgeways, as he explained how he and Angie had met and become friends.   A couple of times she tried to tell him that she wasn’t like other girls, and began to worry about it.   Every time she began though, Glen somehow managed to change the subject.

Once they’d picked up the pizza, they agreed to go back to Anna’s, and caught a taxi.   Once in the warm, Anna got plates, and they sat on the sofa and ate.   Glen seemed unable to stop talking as if he was nervous, but Anna was beginning to feel drowsy.   Suddenly, Glen was sitting next to her, kissing her neck and stroking her arm.   Anna felt alive for the first time in years, and began to respond, then realised what was happening.

“Glen, I’ve got to tell you some..” she began, before being stopped by his mouth pressing to hers.   Anna melted into his arms and began to hold him, feeling his strong shoulders under his thin shirt.   He picked her up, and began to carry her upstairs.

“Please stop, I must tell you..” she started.

“I know, and I want to” he replied, carrying her into her bedroom.   “Angie told me, and I find the idea so incredibly sexy” he said, before pushing his tongue into her mouth.   “You are the most gorgeous girl I’ve ever met.   Angie said you were, and I would like to make love to you if you want me to.”

I’d love you to please” Anna replied breathlessly.

They began to undress each other, until they were both down to their underwear.   Anna sat on the end of the bed, Glen kneeling between her legs.   She began to say something but Glen just told her to shush.   He gently drew Anna’s panties down her legs, revealing her small, soft, shaved cock.   Anna sat tensely on the edge of the bed, ready for Glen to cry his revulsion and run away.   Glen appeared to move forward for a better look, and then leaned forward and took her penis between his lips, running his tongue along the shaft, and around the head.

Almost unbelievably for Anna, she felt her cock begin to harden under the stimulation of Glen’s lips.   She moaned and buried her hands into Glen’s thick hair, pulling him further into her groin.   Glen began to push back, and she regretfully released him, feeling a sense of loss which she could almost taste.   He had awoken feelings in her which she did not think possible.

Glen stood and pulled his boxer shorts down over then end of his thick, hard manhood, his glans engorged and throbbing.   Anna tentatively leaned forward and took the head of his cock between her perfectly painted lips.   She explored around the head of his penis with her tongue, poking the end into the tip causing him to gasp and twitch.   She moved her head backwards and forwards, blowing Glen with a natural rhythm which had him gasping for release.

Glen pulled away, and again knelt before Anna, bringing his mouth to hers, kissing her deeply.   “If you keep that up, you’ll have me coming in seconds,” he gasped.   “I’d like to make love to you if you’ll let me.”

“I’d love for you to make love to me” Anna sighed, unable to believe that this was happening.

Glen went over to his jeans, and pulled out a condom.

“Let me take care of that for you” Anna breathed.

She took the shaft of Glen’s prick, and pulled him towards her.   She stroked his shaft a couple of times, and planted a kiss once more on the head.   She then took the condom and rolled it down the length of his shaft.   She then took a tube of lubricant and placed some in her palm.   She ran her hand down the length.   She then lay back on the bed and raised her legs above her head, presenting her tight brown anus.   She first inserted two lubricated fingers into her hole, pushing back and forth, as Glen took hold of her ankles.   She removed her fingers, and Glen moved his cock forward to take their place.   He pushed first gently, and then more firmly against her hole, until it pushed into her tunnel.   He gently eased his stiff prick in, and then slowly withdrew until just the head was still inside her.

Anna sighed, and moved her buttocks forward, drawing his prick back into her, and together they built a rhythm.   To Anna, it seemed as if every one of her nerve endings was tingling, as if she was hooked up to an electrical current.   On each thrust forward, Glen’s pelvis hit her testicles, causing her still stiff little cock to bounce against her stomach.   Glen found the visual stimulation mind-blowing, and he began to speed up, his strokes shortening and quickening, whilst Anna felt an unfamiliar sensation building.   Glen pumped through his orgasm, grimacing as he shot his sperm into the condom.   Simultaneously Anna felt his shaft swell and throb, and her own shaft did the same as she came onto her stomach.

Glen withdrew gently, removed the condom which he dropped into the bin beside the bed, and again knelt between Anna’s legs.   He lifted her cock between finger and thumb, and licked around the head, cleaning the cum from around both the head and shaft.   He then moved up onto the bed and took Anna into his arms.   They breathed deeply, one hand on each other’s penis, as Glen lay pressed to Anna’s back, and they drifted off to sleep.