Gilligan’s Gift
Chapter Five
Virginia Mitchell had developed her advertising agency from virtually nothing, setting it up after five years learning the industry with that renowned city firm everyone talked about before hers. Now it was hers they talked about. Thirty staff on the payroll it was now, and at forty three she’d considered she’d made it. And she was hot too. Tall at five feet eight inches. Slim. 36C breasts she’d invested in, just so that some of those male clients inclined to dream of their chances with her might, well, dream of it whilst signing on that dotted line. Shoulder length auburn hair invariably raised in a clasp was the norm. Married to Barry for just five years now, and no children, although he had a twenty one-year old daughter Cindy who she employed part-time as a PA. The sex had grown stale though, and that’s why she’d sought out Doctor Gilligan, on recommendation, and had felt so much more in tune with her sexuality now she had. The Doctor had shown her that the issue with Barry was just a state of mind, and if she could just focus on her pleasure as and when those particular occasions of need arose, then all would be well satisfying, and it was. Yes, she’d felt that much comfort since seeing the Doctor that she’d made her own recommendations to him, as he’d asked. Apparently, he was very pleased to have had her step-daughter, Cindy, introduced to him. Cindy was a bit of a stunner too, and at twenty one-years of age was a bit of a magnet for two of the young staff members in B-team. At eighteen and nineteen, probably a little too young for her, but boys of that age are difficult to say no to, because they keep on. In fact, after seeing the Doctor it was rumoured that she’d entertained both of them in the restroom of a local bar recently, but just rumour as it stands. Virginia had not long dismissed young Connie from a brief meeting in her office, when the desk phone rang. “Virginia Mitchell,” she said as she placed the receiver to her ear. “Good afternoon, Virginia. It’s Doctor Gilligan.” “Hello, Doctor. What can I do for you?” She asked. “I need a dirty whore Ginny. Can you help?” The voice said. There was just a moment’s hesitation before she answered “Yes, Doctor, of course. When? Where?” “I’ll text you the address and arrangements,” he replied. “Thank you. Thank you very much, Doctor,” she said. “Oh, and Ginny?” “Yes, Doctor?” “Cindy’s horny for you. She needs a slutty mummy.” “Oh, Ok,” she responded, and replaced the receiver once the line went dead.
Moments after replacing the receiver there was a knock on the door. “Come in,” Ginny shouted, and in walked Cindy. “The Doctor said you needed a dirty daughter to help you come, Ginny,” the PA said. “Yes, Cindy. Lock the door will you,” her stepmother boss replied and turned in her chair, pushing her backside forward a little as she pulled up her skirt. As Cindy walked towards her, Ginny pulled her panties aside to reveal a shaven mound and quickly inserted a finger. She removed it as Cindy kneeled down in front of her and leant forward, pushing her stepmother’s thighs slightly wider apart with the palms of her hands before burying her tongue in the slit in front of her. Once her tongue had slid up and down twice it then moved to find the love bud to focus on. As Cindy began licking faster and faster there, Ginny was massaging her tits through her blouse, focussing on the nipples pressing against the inside of the bra. She came quickly, supressing the scream she so wanted to make. She then leant forward to take Cindy’s cheeks in the palms of her hands and found the lips into which she pushed her tongue. It was only brief, before she pulled away. “Thank you Cindy,” she said. “I won’t need you for the rest of the day. You can go home now.” “Thank you, Ginny,” Cindy responded as she rose from the floor, and made her way immediately out of the office.
As Ginny walked up the path that evening to the address she had been given she was somewhat surprised to see Cindy already at the door, seemingly waiting. Cindy turned towards her as she arrived. “Hello, Ginny. Looks like we’re doubling-up here this evening.” “Oh, are we?” Ginny responded as the door opened. Doctor Michael stood before them, a beaming smile on his face. “Ginny. Sin. Come on in. Follow me.” And they did, into a spacious sort of lobby, with a flight of stairs ahead of them, but into a ground floor room the Doctor went, and they followed. “Take a seat. Ladies. So, who’s my dirty whore this evening then?” Gilligan asked with a grin this time. “I am Doctor,” they both responded simultaneously. “Good, good. Now listen carefully. I have a very important associate upstairs. A very distinguished lady of eighty five-years now, whom you’re going to entertain. Understood?” “Yes, Doctor,” they again responded simultaneously. “Now, she likes her whores to perform with each other for her, for a while. Sensual kissing. Some fingering. Cunt and arse, ok?” “Yes, Ok Doctor,” again they both responded. “Oh, and arse licking. She loves seeing a bit of that. And she’ll expect you to pleasure her that way too. Understood?” They both nodded this time. “She expects you to call her madam, so don’t forget, oh and her son, Mervyn will be watching. He’s sixty, I believe. Pleasure him how she tells you, if she does. Ok?” “Yes, Doctor,” they responded. “Now sometimes she’s into a little watersport. She’ll tell you exactly how she wants that. You may need to drink a little piss. Understood?” “Yes, Doctor. Understood,” they again both responded. “Now, there are two boxes there containing what you’ll need to change into. Then get your holes nice and ready like you do. Once you have, go upstairs, turn left and Mervyn will be waiting. I’ll be watching from somewhere, just to see how things work out. And if they work out well I’m certain you’ll be called upon again at some time. How does that sound?” “Perfect,” Ginny replied, and Sin, for a change, said “Fantastic,” before both moved towards the boxes waiting there for them. Gilligan left them to themselves, and once dressed as required they each pushed a couple of fingers inside their front hole, to ready it as instructed. “Can you do my arse, darling,” Ginny said to Sin as she turned away from her and bent over. Sin kneeled down behind her step-mother and pulled the cheeks apart before burying her tongue in the back hole. Then long slow licks the length of the crack before pushing first one, then two fingers in. Moving in a circular motion she then pulled them out and put them in her mouth to cover in saliva before returning them. “That’s it. Right there,” Ginny said in a voice suggesting arousal. Sin obliged for a minute or so more before pulling out again and standing. “My turn,” Sin said and turned to bend over herself. Ginny’s effort matched her stepdaughter’s in intensity. First her tongue, then fingers. As she worked with her fingers, prodding, pushing, she found those on her other hand moving naturally to between her legs to ready that hole even more. Just short of coming they both were when agreeing all was ready, and they left to meet with Mervyn, as directed.
Gilligan observed proceedings through a two-way mirror. Firstly, his whores performed on each other as directed. Fingering, sucking, licking. A little peeing as well. Sin squatting over her stepmother’s mouth and firing a short stream of piss into it got him well hard, and Ginny licking the old woman’s arse was just as fulfilling. Both performed together on Mervyn’s cock and each took it in their arse as they licked his mother’s clit. The finale was a splattering of cum on their faces that each licked off the other before indulging in a little cum kiss. Then off home they were both sent, each convinced it had in the end been a business meeting, which in a way it was. Gilligan found himself pondering on the way home that night, wondering where this might all lead if he remained unable to satisfy the perverted demons operating in his mind. There wasn’t much lower a depth in depravity he felt he could descend to whilst avoiding anything morally and legally out of bounds. It was the warped normality of what he invoked in others satisfying his needs that always seemed to make it all, well, Ok. He needed a little help at this moment, he thought, and who better than his daughter Circe. He decided he’d arrange to see her when she might next fit him in on her busy schedule. Yes, Circe might just be the answer to the mental turmoil now developing within him…..