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Anal Drill

By Gail Holmes & Nemasis Enforcer

“Time and tide awaits no man, that’s what my father constantly told me, For God’s sake what’s a matter with you, here you are twenty one, and still a bloody virgin. Christ, William I’d lost my virginity years before I was your age. I can tell you, once you’ve tried sex there’ll be no looking back”

At 50, William knew that old Bruce had had a few; and still he could pull, mind you he was a handsome man for his age, but then he didn’t look it.

“I think its bashfulness; I just don’t know what to say?”

“Come lad, I’ll get you laid if it’s the last thing I do, I’ll set it up. Don’t you worry none, the girl in question will know that you’re out to fuck her, think no more of it!” Bruce smiled, “I suppose when you have the need; you take yourself in hand every now and again. I tell you there is nothing better than pussy; it really calms you down if you’re tensed up. If God created anything better, he surely kept it to himself!” Bruce chuckled. “Tell you what; I’ll arrange something for the weekend, it’s only a couple of days off now, we’ll go together, I’ve not been down to old Mary’s in months, make a nice change. She owes me a favour anyway”

“Who’s Mary?” William asked.

“Mary!” Bruce smiled. “She’s a madam that I’m acquainted with; known her for years, could say we grew up together. She was a good lay then, but it’s her tribe now, she only picks the best; youngun’s at that, well in their twenties, that’s young to me but there’d suit you down to the ground!”

“Madam, that’s a form of pimp isn’t it?”

“Catch on quick lad; yes she has a whore house other side of town”

“I couldn’t go with a whore, don’t know where they’ve been half the time” William supposed.

“Selective then are we; tell you one thing, you couldn’t pick cleaner women than her girls. And they know how to give a guy a good time to!”

William made his way home on the Friday evening; he’d been to the nightclub, God there were some angels there; one of which he couldn’t get out of his head, she was a really gorgeous; they’d chatted for what seemed hours, but he just didn’t have the courage to invite her out, little did he recognize that she’d actually fancied him herself.

When he ultimately got into bed she was still on his mind; pulling the bedding to one side, he peered down observing his erect cock, slowly he moved his hand towards the stiff organ, holding it loosely within his fingers offering some form of comfort, it wasn’t long before he sensed the need to massage it even harder; his mind now on the girl. God, if only she knew as to what he was doing, he thought to himself; little did he realize she was doing virtually the same thing, only she’d a soft dildo, not soft maybe, but firm, she was lying back her eyes closed, holding the dildo with finger and thumb, viciously forcing up inside herself, but in her mind it was his cock, well as she visualized it, in her mind it was thick and strong, it’s head mauve in colour. She hadn’t realised he was virgin, perhaps just playing hard to get.

William met Bruce as arranged, he was still uncertain of himself.

“What if she doesn’t take to me?” He quizzed as they walked up the steps to large house.

“Fear you not lad; she’ll be willing to go once she knows you fancy her!”

“How will she know that pray?”

“Just you tell which of them you take a liking to, then leave the rest to me,” Bruce said ushering him into the door as it opened.

“What a nice surprise!” William’s friend Mary smiled holding the door wide allowing them both in.

“This err’ is young William whom I spoke of; I’m sure you have something to entertain him?”

“We surely do; what would you like to drink then? I’ll get the girls down then he can make his choice to whom he’d like to spend time with” Mary smiled toward William offering him a seat.

“Couple of beers if you don’t mind, they’ll do fine” Bruce responded, walking toward the window and looking out.

“You won’t believe the talent Mary has here bless her, you’ll be stuck for choice once you see them?” He declared without turning from the window.

“Still don’t know if I’m doing the right thing, I really don’t know where to start!” William implied, watching the doorway as he heard noises outside.

“You just tell me which one you consider!”


“Consider you’d like to fuck! Come on William where are you, this is going to be your big day. After today, you’ll be able to fuck whatever takes your preference. The amount of females out there just waiting for you to fuck them”

William made no response; suddenly he was lost for words as the girls came into the room, followed by Mary. All were dressed in short mini-skirts with open front blouses, a hornier sight he couldn’t have wished for.

“Here we go then; two nice cool beers!” Mary smiled as she pushed her way through the girls. “No you stay sitting young man,” She told William taking one of the glasses of the tray handing it to him.

“My your stock gets better!” şişli escort Bruce implied looking at the girls as he took he’s glass from her. Watching as they milled past William, flaunting themselves their dress being sufficient to turn any man on.

“I can see you’ve not misplaced your craving for the young set then?” Mary grinned toward Bruce, who had now sat down for a better view of their legs.

“That’s what I’m here for!” He mused his eyes glued on the girls.

Two of the girls each sat aside of William on the large sofa; mutually knowing he’d taken a desire to them, one thing about women they have the inner sense when it come to aspiration within a mans eyes.

William lifted his glass to his mouth as to take a sip, feeling somewhat embarrassed by the suddenness of the girls movements, that was until one took it from his hand; placing it onto the table to the front of them.

“Later!” she smiled.

Bruce had not missed out on the array of females so scantily dressed, one was now sitting on his lap, hugging Bruce around the neck; he pulled her to his ear, whispering something that only she could hear. The girl looked up toward William, smiling she opened her legs but only slightly, but it was enough for him to see the delicate underwear she was revealing to him. One of Williams’s girls started undoing his flies, it wasn’t before time either, his cock launched its self like a jack-in-the-box, immediately she took it into her hand, the other girl got down onto the floor sitting in front of him watching every move her friend made with his cock. Suddenly she went down on him; William threw himself back into the sofa, the sensations of her gobbling sent his body into seizure, never had he experienced anything like it.

The girl on the floor was now removing his jeans pulling them down over his feet. From the waist downwards he was now naked. He felt somewhat exposed; nevertheless his mind was elsewhere. He casually looked across toward Bruce, who’s hand was now up between the girl’s legs tugging at her silky white panties, he caught a glimpse of the pubic hair, abruptly Bruce’s fingers vanished inside. The girl was kissing him passionately as if his fingers had willed her to surrender.

Both girls were now sucking Williams’s cock in turn, the sensitivity was extraordinary; he looked down at the two bobbing heads in his lap. He was certain at this rate he’d cum; the girls who was sitting next to him climbed over his body striding his lower torso, she lifted her skirt as if to show him her bits, after seeing as to what Bruce had done, as did he; his hand cupped her pussy area over her panties. The girl looked into his eyes

“Go on, it’s yours!” She grinned, and then leaning forward kissed him soothingly on the lips.

This seemed to have a considerable effect on him; his fingers were now delving to the side of her panties, the soft skin and puffiness of her pussy, sent tremors through his body. As the girl started to lower, the other still sitting on the floor took hold of his cock guiding it to the descending pussy. William eased himself back into the sofa; the sensation of her pussy on the end of his helmet was orgasmic.

“Jesus!” He exclaimed, catching his breath.

Gradually the girl sunk her pussy over his cock until it was fully immersed within; leisurely she started to rise and fall. The girl on the floor now got up sitting beside him, whilst her friend with hands on his shoulders started to fuck him in intensely. William clasped her waist lifting his hips to her movements. Her friend reached between them lifting the skirt revealing the erotic sight of his cock thumping up into her pussy.

Bruce looked across toward William, watching him in his moment of glory.

“Well lad, what do you think?” He grinned.

William shut his eyes then shook his head. “Never, ever would I have surmised it would be anything like this!”

The girl’s friend had now got off the settee and was removing her clothing. William watched, as her body became reality, never had he seen a nude female only in pictures.

The girl on his lap leaned forwards kissing him in a gently manner, and then stepped to one side whilst her friend moved into her place. It was a lovely sensation, from a wet and moist pussy to a moist but tight one. William reached up cupping his hands over her breasts, then kissing them individually.

This was certainly a new experience to William; by no means had he ever became aware of feelings such as this with his hand, it was a new height to his awareness of the female form. It was sensational, hard to explain, with one’s hand you can only cover so much of your cock he thought, but this, this was captivating his whole cock in one go, the two sensations we’re worlds apart. Abruptly the girl’s body seemed to freeze up, she slumped over his shoulder, her breathing somewhat heavy. William tried to lift his hips, but he was locked solid.

She eased herself back off his shoulder and gave him a peck on the cheek. “How d’you do that, it was breathtaking!” She murmured as if still not altogether having her wits about her.

“What did I do?” William questioned, not quite understanding as to the quandary

“Hell I don’t know; but you certainly knocked me off my perch” The girl sounded exhausted.

William’s cock was still deep inside her as she turned back to her friend.

“You’d better take over now Emma, I’m totally bushed. God, nobody has left me this exhausted, he’s drained me!”

Emma stepped forward as Ellie strained to lift herself off of his proud cock.

“I hope I didn’t hurt you in any way?” William informed her.

“Hurt! No way did you do that, but that’s some cock you have there, never has anybody given me so much exhilaration, it was shattering”

Once again his was subjected to a moist but tight pussy, and he’d only left fucking her about ten minutes ago. He couldn’t make out for the life of him as to what he’d done to Ellie. Emma lowered, unhurriedly still wondering what he’d done to her friend, his cock felt good to her, she continued to fuck him, however she was anticipating something happening like it had to Emma, She rode him hard all the way up; thumping her pussy down hard, assuring it was fully inside her. William’s cock sensed every ripple inside her pussy, it was like walking in heaven, and he was in a dream world of his own. He was glad that he’d got Ellie back; after all she did take his virginity. Unexpectedly he sensed the expected, but he’d have sooner have liked to carry on but his heart was pumping he knew he was about to cum. However, he was not in control, Ellie was, he could only lift up to her, the chances of him pulling out, were slim. Ellie sensed the fullness of his cock she knew his seed was on its way; William let out a loud gasp as he came. She held her pussy down onto his cock giving him the real experience of the swelling within her pussy. He sat pushing himself upright, placing his arms around her.

“God, that was a magnificent experience, it felt really excellent!” He told her as he slumped back against the sofa.

As Ellie lifted herself from him, there was a thick dribble of his cum hanging from her pussy. One of the girls rushed forward going down in front of her; William was amazed to see her actually licking the cum out of Ellie’s pussy.

Mary noticed his expression “We waste nothing here young man! It’s all part of the service, always cleaning up after us” She smiled.

William twisted toward Bruce; he’d a girl on her knees in a chair, fucking her like there was no tomorrow, the noise she was making made him wonder if he’d done the right thing, still, he did come here to get fucked, and he’d genuinely enjoy it. After he’d replaced his clothing he picked up his glass and sat down watching Bruce. The girl was nearly screaming now, he was really driving into her; suddenly he humped his cock in deep and blew his load with a loud moan. The poor girl nearly collapsed in the chair after he’d pulled out. He swung around, he’s cock swung to and fro.

“Is there any more beer Mary!” He inquired without any form of shame, with his cock flopping around.

“Coming right up” She replied, leaving the room.

“Well lad; did you enjoy it?”

William felt somewhat humiliated by him keep calling him either lad or son, certainly the girls found it amusing as they started to giggle.

“I certainly did, we all have our first time with everything!” He replied; this seemed to quell the giggling to an extent.

“And what’s more he’s very good at it!” Emma smiled. “Never ever have I had an orgasm such as he gave me, lessons could be learnt from him?”

Poor Bruce didn’t know what to say; for a girl to say such a thing to him knocked him for six. He did speculate if he’d done the right thing bringing him here in the first place, perhaps the lad wasn’t as naive as he originally thought.

When they’d both left Mary’s; Emma gave William a nice kiss on the cheek. “You will come back won’t you” She requested.

“Made quite a name for yourself by all accounts; though you were suppose to be a bloody virgin?”

William didn’t really need this, he still didn’t know as to what he’d done to make the girl applaud him; after all she was doing all the work.

“I was; I can assure you of that, whatever happened she did it herself, I haven’t a clue as to what could have occurred?”

“Well you certainly made me look a fool, I’ve been at it for years my boy!”

“There is no way I would have done anything to upset you; I would however appreciate it if you’d stop calling me boy and lad, I find it can be embarrassing at times!”

The following week went by, Bruce didn’t have a lot to say about Mary’s place, and William didn’t think he’d be going again, well not with Bruce anyway. He’d only wished he could remember what had happened with Emma; but it did spur him to go to the nightclub the following Friday night in the hope of finding the girl again, now he’d lost his virginity, he felt more secure, at least he knew what it was all about now.

The club was extremely busy, she never turned up until 9.30 even then she seem to give him the cold shoulder, he could only assume that she’d supposed he’d given her the brush off the Friday before. Even then he felt that if he had made a date he’d have let the side down. Finally she succumbed to him, but it was quite late, her name was Angie she was a very pretty girl, quite tall, slim but an hourglass of a figure with ash blonde hair down to the middle of her back, William didn’t think he’d a chance with her. They did two or three dances together before the end of the evening.

“Do you have lift home?” William asked her as they made for the club exit.

“No, I live on the outskirts of town”

“With your parents?” William inquired.

“No, have my own flat, it’s quite nice, would you like to stop by for a coffee?”

“Sounds great to me, we’ll get a taxi if you like?”

“Sooner walk if that’s okay with you, it’s a nice night and I feel quite warm after being in the club” Angie took his arm as they started to walk.

It took around twenty minutes to walk to Angie’s home, it was in a nice area of the town, William realised the she must be an influential girl as the property was well up-market, she must have a good job with excellent pay to afford to live in this neighbourhood.

“What do you do for a living?” William asked as they entered the flat.

“I have my own business, in Keep Fit!” Angie smiled. “This is a lovely flat, it must cost you a fortune?”

“Well it’s my Dad’s really, he’s the one with the money. Here let me take your coat!” After William had removed his jacket, Angie hung it in the small reception area. “D’you prefer coffee or would you like a proper drink, I even have beer should you wish?”

“Beer would suit me fine”

When they entered the lounge it took Williams breath back, everything seemed brand-new, and everything was so spotlessly clean.

“You live here alone?”

“I suppose you could say that, except for Mr. Ollie that is” She smiled.

“Mr. Ollie?”

“He’s my cat, he’s still out by the way…I’ll shall have to call him in; I must take a shower now, that club make you feel so uncomfortable with its heat. Please help yourself to a beer, you’ll find them in the cooler behind the bar over there!” Angie pointed to a small bar set into the corner of the room. “Put some music on, I shouldn’t be to long, smoke if you want to”

“I don’t!” William smiled as she left the room.

He collected a beer then sat down on the settee with a handful of CD’s he’d collect from the music centre. It certainly was a spacious flat, and the pile on the carpet was knee deep. He wondered what her father must do to afford a place like this. After selecting three CD’s he then put them in the music centre.

“My I like you’re selection, we’re not to far apart there!” Angie laughed as she came back into the lounge in just a dressing gown. “Sorry if I’ve taken to long, like another beer?”

William looked up as she stood in front of him, sexy wasn’t the right word for her. “Fine I’ll get it, can I get you something?” he suggested looking back as he made his way to the bar.

“Just an orange with ice if you wouldn’t mind” she replied with a smile could melt any mans heart.

“Nothing stronger?”

“No, I only drink juices, sorry I’m such a bore aren’t I!”

William smiled back to her. “Not at all; you have whatever suits you”

Angie moved to one side as William brought the drinks back, leaving very little room for him to sit. It was obvious that she intended to be close when he did sit. He was in a quandary; he really didn’t know where to start, he knew she wanted him as he did her, but you don’t just jump into sex, well he wouldn’t have thought so, he’d tried to get the low down on the technique from Bruce, but after being at Mary’s he’d spoken very little about sex.

“You look lost?” Angie grinned up to him as he stood holding the glasses. “Come on sit yourself down”

She took her glass from him; tapping the cushion beside her, but still never moved. William virtually wriggled in beside her.

“I would say you’re a mite shy?” She smiled holding her glass out toward him, “Cheers”

“Cheers!” William replied with a grin, “You’re right; yes I am shy to a extent.

Angie reached for his hand; taking it into her own, “I think you’re cute”

“Funny I was thinking the same; of you I mean” He smiled.

Angie moved her hand down onto her leg taking his with it.

William’s stomach flipped as he felt Angie’s hand pull his onto her thigh. He remembered back to when he had first seen her in the club, she was so good looking and he wanted so bad to go and talk to her, even bring her home with him but he hadn’t the nerve to do it.

Now here they were, on her sofa, his hand caressing her inner thigh as she smiled to him, her eyes bright and inviting.

Angie’s mind went to the same night, the night she had gone home and masturbated thinking of the cute guy in the club, he was so nice and she wanted him, now she had him and he wasn’t going to get away from her, not this time.

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