Lucy was a very pretty looking girl next door type of 27 years with a lovely womanly body and almost permanent smile though at the moment she wasn’t very happy as her parents business was struggling and was close to closing down. One big problem was money owing to a local business man, Mr Holland, who had a certain reputation and she’d overheard her parents saying that they had wished that they’d never got involved with him and the money they owed him could be the end of the business, and he wouldn‘t budge over the price owed or that he wanted it straight away. Lucy was a bright young woman and decided to go and see Mr Holland to see if he would let them have more time to pay and lower the price. Lucy arrived at Holland’s house and knocked on the door and the door opened to reveal Mr Holland a large man in his late 50’s and Lucy explained who she was and asked if he’d consider the price and payment time. Holland smiled “come in young lady” and lets talk business. Lucy entered the house and they went into the living room where Holland offered Lucy a drink and she accepted a glass of orange squash. “Right then young lady how does this sound and I’m going to be blunt you‘re doing business with the big boys now……I have a customer coming for a meeting tomorrow and he’s staying in a hotel overnight. Now I usually pay for customers to be ‘entertained’ by a professional lady but that costs a lot of money for an overnight stay and I am sure that they would be much happier if you were to ‘stay and see to their wishes…you’re a lot fresher and prettier than most…what do you say?” Lucy was shocked and nervously stuttered “Y you mean you want me to have sex with him and you’ll reduce the money my parents owe and give them longer to pay?” Holland smiled “that’s about the top and bottom of it…you could say that you use your hole to get them out of a hole! I‘ll then knock the money owed by them down to say £5,000 from £6,500 and give them two months to pay how does that sound? I‘ll even promise that this stays between me and you by us having sex sometime and you could then tell my wife if I ever told your parents.” Lucy’s mind was whirring and she knew her mum and dad needed help “OK I’ll do it” she blurted and the pair made the arrangements where Lucy would have her own room at a local budget chain hotel and Holland would bring the man along to see her. Lucy left Holland’s house and Holland looked at the pretty girl walking down his driveway “you’ve got a lovely bum young lady.. I wish I had more time now to have my part of the deal!” The following evening arrived quickly and Lucy checked in to the Hotel and there was a knock at the door which she opened to find Holland “Ah Lucy good girl you’re here….thank you for putting on a nice dress. Now I’ve spoken with my customer his name is Brian he’s a bit rough and ready in his manner and he’s asked that I stay for some reason is that OK with you?” Lucy thought briefly and she knew that Holland would see her naked soon anyway when he wanted to have sex with her so she just nodded her head. “Good, Good, now the language may be a bit fruity but just let him do what he wants to you and we’ll all get what we want.” Holland stood up and took the door key “right I’ll go and get him.” Lucy’s heart was racing and she heard footsteps walking towards the door and voices and she wondered what the stranger she was going to have sex with would be like. The noise of the swipe key was quickly followed by the door opening and Holland led in a portly man in his late 50’s early 60’s. “Now then Brian this is Lucy the young lady I was telling you about who has agreed to entertain you this evening…she’s got a lovely bum from what I saw when we met yesterday when she was wearing jeans and look at those lovely tits you’ll have fun playing with them won’t you?” The older man was smiling and licking his lips looking Lucy up and down “you’re right those funbags look like they’re going to give me a lot of fun and she’s certainly a looker” said Brian. “You know what Ted” said Brian to Holland “I’ve not seen a naked woman for 15 years since my wife left can we get her naked so that I can remind myself what a woman looks like nude…..in any case I‘ve never seen a naked woman as pretty as this young lady ever!” Holland laughed “OK Lucy sounds like its time to get your clothes off and show Brian everything you’ve got.” Brian looked Holland “you’re staying to watch aren’t you” and Holland smiled “don’t mind if I do” and both men grabbed a chair and sat down. “Come on then love lets have a look at your tits and cunt” said Brian. Lucy looked down and unbuttoned her dress and at the same time kicked off her shoes and before long the dress had fallen to the ground and left her in just her bra and knickers. Lucy’s hands went behind her back and undid the bra clasp and she allowed the small garment to fall from her body and let her lovely C cup size breasts wobble free for the men to view “lovely titties eh Ted” said Brian “certainly are…just look at those nipples eh” said Holland. Lucy put her thumbs in the waistband of her panties and slowly pulled them down “ I can’t wait to see her fanny” said Brian and Lucy kicked off her knickers and she was now totally nude in front of the two men. “Get on your back then and open your legs so we can have a look at your gash” said Brian and Lucy moved to the bed and shuffled so that she was on it. The two men edged their chairs forward to the edge of the bed to get a better view of the pretty young woman’s intimate area between her open legs. Slowly Lucy raised her knees and she took a deep breath as she lowered her knees and leave her legs open for the men to look between them. Lucy looked down at the two old men leering between her legs “God did a wonderful job here with her what a beautiful view” said Holland “yes indeed just look at her slit hiding behind her pubes” said Brian and Lucy knew that they were both looking at her vagina. “Pull your piss flaps open” ordered Brian laughing “I want to see your clit and inside your hole“. Slowly Lucy‘s hands went down between her legs and she parted her labia to reveal her hole and clitoris to the men. The two men were smiling as they had a good look “You’ve done me proud here Ted…I can’t believe I’m gonna get up inside that tight little cunt soon…..are you going to have a go on her as well” asked Brian and Holland just smiled and nodded and whispered “oh yes!” Lucy looked up the two old men looking between her open legs from only about two feet away as she held herself open for them and wondered how long it would be until one of them got inside her. “Right then Ted I reckon it’s about time she showed us this lovely bum that you’ve been telling me about” said Brian and Holland smiled “come on lovely Lucy get on your hands and knees and let two old men have a look up your bum…you don’t mind us seeing your bumhole do you now. ” Lucy started to feel a little humiliated as she shook her head and tears started to well into her eyes so she turned over quickly as she didn’t want the men to see that she was embarrassed. Slowly Lucy raised herself onto all fours with her bum towards the men “Mmm yes look at her puckered little poohole she’s got hiding up her bum crack lovely ain’t it” said Brian and again Holland could just nod and smile. The men’s necks craned to look up Lucy’s bum “look at those milkers hanging down as well” said Brian “am I Ok to touch her now?” asked Brian and Holland looked at him “Brian you can do what you want to her she’s yours for this evening…..go on get your face up her bum and lick her shitter…you can play with her tits at the same time.” Lucy braced herself as she felt hands running either side of her ribcage which then went below her and groped and squeezed her beasts and nipples. “That’s a prime bit of tit meat no sagging here” said Brian to Holland as he mauled the young woman’s mammary glands. Brian’s left hand continued to feel Lucy’s left tit and his other hand roamed over her back and then over her bum crack. Slowly his hand got braver and his fingers moved down her crack until they got to the pretty girl’s anus which he gently tickled. “Come on Ted hurry up and give her a rimming” said Holland teasingly and Brian looked puzzled “you know what I mean…get your tongue up her bum and lick her ring piece.” Brian smiled “I’ve never done that before…but she is rather gorgeous isn’t she” and Brian got off the bed to move to Lucy’s rear end and Lucy looked round at Brian “are you going to lick me there?” she asked and Brian smiled and played dumb to make Lucy embarrassed “Lick you where? he replied forcing Lucy to expand and clarify her question “you know…lick me up my bum….my arsehole nobody has ever done that to me before” and Brian laughed “well it’ll be a first for both of us then sweetheart” he said. Brian winked at Holland and lowered his face until it was pressed between Lucy’s bum cheeks and Lucy felt his tongue lick over her anus and then the length of her bum crack. Brian’s tongue then licked from the top of Lucy’s bum crack in the opposite direction until he reached her anal opening and started to lick the young woman’s hole enthusiastically whilst breathing quite heavily. “How does her poohole taste and smell then Brian” joked Holland. Brian continued for a few more minutes before removing his smiling face from Lucy’s bum “wow that was fantastic…. I’d clean her arsehole with my tongue any day…..I don‘t care that she shits out of it that was wonderful!” Lucy was still on all fours and she could hear clothes being removed behind her “OK love get on your back and spread your legs open I want to fuck you now” and Lucy did as she was told for the old man. Brian climbed onto the bed now naked and got his portly body between Lucy’s open legs and his hand guided his cock to her vagina. Slowly Brian’s body pushed his cock between Lucy’s flaps which stretched to accommodate his member and Brian was now fully inside her hole and enjoying fucking her lovely young 27 year old body. Brian’s right hand was feeling Lucy’s tit as he moved up and down in and out of her as Lucy lay back passively allowing this older man to have her. Lucy looked up to see Holland standing and looking at Brian between her open legs in the air either side of him “tell you what mate I reckon you should let her go on top I’d rather look up her bum whilst you’re fucking her than yours… and you get to play with both of her tits!” Brian smiled “you’re right mate I’m too old for doing all the work and she has got lovely tits and nipples for me to play with!” The old man got off Lucy and lay on his back on the bed and she felt his cock leave her body and her hole close, temporarily! “OK girl on you pop….let’s see how deep I can get up your hole in this position I know my friend Ted here is keen to have a look up your bum at your bumhole again whilst I’m fucking your cunt” laughed Brian. Lucy climbed over the man and put her hands on his chest as she lowered herself until she felt the cock probing for her female opening and then it entered her body until it was fully engorged by Lucy’s hole. Brian’s hands were mauling the lovely breasts hanging in front of him from the chest of the very pretty young woman as Lucy rose and sunk her hips for Brian’s pleasure. Lucy looked round to see that Holland had moved the chair directly behind her and was sitting forward with his head to one side about a foot away from Lucy’s intimate parts watching her having sex with his customer. “What’s the view like mate?” asked Brian “absolutely superb…..every time she moves up your cock it exposes her flaps and when she moves down they vanish inside her hole along with your cock you jammy bastard” and both men laughed out loud. “I bet you’re enjoying looking at her poohole up her lovely bum as well….how’s that look?” and Ted nodded to himself as Lucy’s bum cheeks were extended apart and he had a perfect view of her exposed anus in her bum crack less than an inch away from her labia “it looks fantastic so beautiful” said Holland. Brian laughed to himself “what you waiting for man why don’t you get up it….go on get up her arsehole.” Lucy looked anxiously round at Holland whilst still fucking Brian and nervously said “I…I’ve never done that before” and Brian was looking deep into her eyes and excitedly said “let me do you up your bum and I’ll half what is owed and put the payback to a year.” Lucy knew that this would really help her family business in reducing the large debt and having longer to pay though she was worried at never having had anal sex before never mind a cock in each of her private holes, and she knew she may be able to get better deal with Holland being so keen to bum her. Lucy’s heart was racing faster than ever “knock the debt down to a half and you can put your finger up my bum….but If you knock it down to a quarter you can put your cock up my bum whilst he’s up my cunt as you both like to call my vagina.” Holland was very excited indeed and nodded and shouted “YES” in agreement. Lucy couldn’t believe what she had just agreed to and Holland thought he was in heaven that this very pretty girl was going to let him put his cock inside her back passage which had been taboo to all other men - he now knew why he’d always wanted to have money! Lucy looked round again “I know that you wont need me to encourage you but you’re going to have my anal virginity please please work in something to lubricate my bum so it doesn’t hurt me so much.” Holland’s mind was a step ahead and for the second time in a short period of time an older man’s face was up her bum licking and spitting on her anus “what is it about my bum that you two want to get your tongue’s up it and you want to fuck it” asked Lucy and Holland laughed “well Lucy you are a very pretty young lady with a gorgeous body and superb bum that normally handsome young men would ever likely get chance to see…..so for two old gits like us to get to look up your bum and see your very private bumhole is an honour…..to lick your bumhole which you shit from is an even more exciting and dirty thing to do to you as its so naughty…….but for me to have the honour of being the only man to put his cock up your shitter it is the ultimate for me.” Lucy felt a finger tickle round her anus and slowly ease inside the hole pushing her sphincter open “just opening you up a bit” said Holland. Lucy had stopped fucking Brian who was still inside her and still squeezing her tits as Holland pressed the head of his cock up to her bumhole…..slowly the old man pushed forward and he smiled with pleasure as he felt the young woman’s anus slowly start to give as he entered her. Gradually his cock entered a smidgeon at a time and Lucy panted as it did so “what’s it like….are you bumming her yet?” shouted Brian and Holland smiled “you got it mate I sure am bumming her she’s being buggered for the very first time!” Both men let out a cheer and started to pump into Lucy’s two intimate holes and both men groped her tits as they each enjoyed the young 27 year old body. Holland’s cock pushed deep into Lucy’s rectum “Christ that’s a tight hole you’ve got girl….what feel like having my cock deep up inside your bumhole?” Lucy thought for a moment “it feels like you’re trying to push something along my spine” and Holland smiled. The two men double penetrated Lucy with only her perineum externally separating their cocks and suddenly Holland started to jerk and then let out a noise as he ejaculated up Lucy’s bum deep inside her bowels. Holland withdrew his cock and watched as Lucy’s tight anus returned from being open to its normal tight self trapping his sperm inside. Brian was still going well for an old man and rubbing his cock against Lucy’s internal vaginal walls until he eventually came inside her and washed the cervical entrance to her womb with his spunk. The three people lay naked and exhausted until Lucy got up and said that she was going home knowing that she’d helped out the family business. Brian and Holland both gave Lucy a hug as a last opportunity to feel the lovely naked woman “Thank you for making an old man very happy young lady, you’ve got lovely tits and a super tight little cunt hole” said Brian pulling Lucy close to her so that her tits pressed against his flabby chest and Lucy gave him a short smile not believing that she’d just let this old man have her body and look in all her intimate places for a business deal. Holland then hugged Lucy allowing his hands to run all over her back and a last feel over her bum and her left tit and whispered “Brian’s just told me you’ve got me the deal I was after as my competitor had only given him a bottle of whisky….thank you for letting me do you up your bumhole I know it was difficult for you to let me up there but it was fantastic for me….perhaps we could something similar some time?” Lucy smiled “I think I’ll keep a closer eye on the family accounts in future!”