Mrs. O'Grady's Boarding House

After another few moments he took the initiative and reached down to unfasten her skirt waistband, allowing it to drop to the floor where she stepped out of it, totally naked. He held her away from him a little, admiring her body, remembering when his darling wife was also lithe, young and sexy like Jessie. It was so long ago, but yet he could remember her so easily.

Jessie was encouraged by the small tenting inside his underpants. She wanted to encourage this so did not remove them yet, instead she cupped his balls with her hand and resumed kissing and caressing him. A few moments later she drew him over to her bed and they lay beside each other, their upper hands continuing the stroking while her lower hand began rubbing his cock through the reasonably heavy fabric of his underpants. She was rewarded by an increase in stiffness, which Claude noticed.

"You must be magic, darling, this is the hardest he's been for many a long year," he commented.

"That's good, darling, just let him keep growing. Why don't you rub your hands over my pussy and let your fingers play between my lips. I'm sure you'll find they're very wet and aroused for you."

Jessie rolled a little more onto her back and spread her legs as an invitation to Claude to continue his ministrations a little lower down. He caressed her pussy, stroking her small patch of hair, introducing one finger, then two, between her lips and spreading her lubrication around. Meanwhile she continued to stimulate his penis and, when she felt the time was right, she moved her hand inside his underpants and began stroking up and down his semi-hard organ. After a short time she stopped and reached over to her dresser to retrieve a tube of lube, which she applied to her hand then to his penis. Immediately he hardened still more, then he screwed up his face as he felt her stimulation, the most he had felt for a very long time.

"Ooohhh, honey, that's beautiful. Thank you darling, thank you, I so needed that."

"Just you relax and enjoy it," Jessie replied, "You deserve to feel this stimulation. It's been so long, just relax and enjoy."

While Jessie wanted to give him a great deal of exquisite pleasure, she remembered his fondest wish was to make love to a woman, so she was careful not to stimulate him anywhere near enough to reach his orgasm. Instead she monitored his erection and when it was sufficient, she sat up, took a condom from her drawer and rolled it expertly onto his rampant cock.

"Sorry, sweetie, but rules are rules. Now, come and put that hard cock in my slippery vagina and fuck me good like you want to."

She lay on her back, legs wide spread and helped him position himself on her, moving him so he was at her entrance. He then pushed his cock into her. Jessie felt it slide in effortlessly due to her own lubrication and to the fact it was a lot smaller than most of the others she had felt during the past weeks. She helped him push it fully inside, then began a forward and backward movement with her hips, forcing his cock deeply inside her, then moving backwards so it was almost completely out. Effectively, she was doing all the work, simply allowing Claude to rest on her while she made love to him.

Gradually he became more aroused, contributed more to the motion, and became more vocal, grunting each time he pushed into her. She kept up the motion and slowly increased the speed, partly to push him towards orgasm, but also to push herself towards her climax, which she felt she would need very soon. She reached behind him and used her hands and arms to hold his ass and move him on her, pulling him away so he was almost out of her, then pulling him forwards until her clit pressed against his pubic bone. She noticed that the end of his cock, when fully inside her, was nowhere near the end of her vagina, unlike some studs she'd had in the last little while.

His breathing rate increased along with his arousal. He nuzzled his face into her neck briefly, lifting it for deeper breaths. She kept up her rhythm, forcing him to follow, using him like a fuck toy for her own pleasure, while also giving him the pleasure he so desperately missed and needed. His breathing more rapid and he began a whining, humming sound until, without further warning, he held firm while fully inside her and she felt his cum spurting through his urethra into his condom. He held his breath for a long time, then let out a sigh before panting rapidly and lying almost semi-comatose on top of Jessie.

After several minutes he seemed to recover and pulled his shrunken cock from her vagina, Jessie having to hold the base of the condom to ensure it remained on him. She felt very sexy, very frustrated and slightly bitchy, as she always did when she had a session without cumming. This time she realized it was not due to a careless attitude, simply to inability, so she forgave him.

"Well done, darling," she complimented him. "Did you enjoy that?"

"Oh yes, Jessie, thank you so very much. You've made my dream come true. But did you cum, honey? I know you always like to cum when we make love."

Jessie realized that in his mind she was still his dearly beloved wife. "No, sweetheart, I didn't. Would you like to make me cum with your fingers?"

"Yes please, if you'd like me to and if you'll let me."

"Mmmm, yes, please do, darling."

He sat beside her on the bed, one hand rubbing her clit, the other squeezing and caressing her nipples. Jessie closed her eyes and felt the sensations swallowing her up, taking her closer and closer to her orgasm until, suddenly, she was there.

"Yes, darling, ooohhh, yessss, oh honey, it's wonderful, yes, yes, oooohhhhh," she cried as she came hard while he held his hand still, keeping pressure on her clit as she writhed on the bed. After a short time she relaxed, opened her eyes, and looked softly at her elderly lover.

"Thank you, darling, that was wonderful. What a considerate lover you are. I hope yours was great too."

"Oh yes, Jessie, mine was fantastic. Even more so because I didn't think I could make love like that ever again. Can I come back and see you again please?"

"Anytime you wish," replied Jessie sincerely, "I'll look forward to your visits."

They cleaned themselves up and dressed once more, then Jessie walked him back downstairs and with a final kiss he stepped out the door, promising to return next week.

"How was he?" asked Trish.

"Poor old guy. His wife died and all he wanted was to make love once again. He was OK for a guy his age and yes it was a very satisfactory session, although I will appreciate someone more lively and challenging next time."

"I'm sure we can arrange that. Pleased it went so well. It must be really hard for elderly single guys, nobody really wants them, they don't feel needed, maybe don't have anyone to talk to. Aging is certainly cruel to some people; no wonder they say that only the good die young."

"Yes, that's true, but also remember that experiencing aging is a privilege that many people do not have, so I guess he really is fortunate in many respects."

"True. Anyway, you're certainly my number one go-to person for potentially difficult cases, so you should have a few interesting guys in future. Thanks for being willing to go that extra mile to help them." Trish gave Jessie a totally disarming smile as she turned to walk away.

Jessie walked thoughtfully up the stairs to her room and lay on the bed, relaxing after her session and contemplating the many sides of growing old, as well as what she would eat for dinner.

She never saw Claude again. A few weeks later she received a letter from an attorney which simply said:

'In accordance with the wishes expressed in the Will of the late Claude Edward Fitzgerald, we have enclosed a check for one thousand dollars. Please sign the receipt and return it in the reply paid envelope.'

Jessie sat in her chair after opening the letter and wept; she wept tears of sadness for the elderly gentleman who seemed to have lost so much of what he loved in his life; she wept tears of gratitude for having been able to help him restore his manhood, that which he most desired, shortly before he passed from this life; she wept tears for the cruelty and disillusionment that people suffered due to the ravages of old age and the attitudes of others towards them; and she wept tears of joy as she imagined Claude and his darling wife reunited forever.

***********************

True to her promise, Trish allocated Jessie all the clients which could be classed as difficult, but which Jessie found to be interesting and challenging. This occurred so many times that the other girls recognised that they no longer had difficult clients and also felt twinges of envy that Jessie seemed to thrive on these challenges. So Jessie was unsurprised when Amy broached the subject.

"How come you get so many interesting and unusual clients?" asked Amy as they shared a drink in the bar one quiet afternoon.

"I guess because I don't have too many preconceived ideas about people," replied Jessie after giving the matter a few moments thought, "People are just people. They come here for a wide variety of reasons like company, friendship, sex of course, but many are simply lonely, unloved and possibly feel misunderstood."

"Yes, I guess many of them are. I never thought of it that way, I tend to categorize them into either people I'd have as a friend or people I wouldn't, and then I tend to shy away from those I wouldn't. So you're saying that you look at things from another perspective?"

"Yes," replied Jessie, "We're part of a service industry; love has nothing to do with it, whether we like the client or would choose them as a friend has nothing to do with it. Actually, I guess it does because very often we find in the person that which we expect to find, so if we've prejudged the person, maybe as being undesirable, we will find that he is undesirable because that's what we'll be looking for. That prejudgement also causes us to act in a way that brings out the worst in the person, so that is, of course, what we see. It's a self-fulfilling prophecy."

"Oh, and I guess that's the same with everyone we meet then," suggested Amy.

"Absolutely. And it's the same with life itself; we find what we seek. If we look for misery, we find it, if we look for happiness we find that instead. The situation doesn't change, it's just our perception of it and our interpretation of it that changes."

At that moment Trish came towards them purposefully.

"I realize that it's your time off but we have a very special client who's just arrived and there's nobody else around; they're all either out or with clients. Would either of you girls be able to help this guy please?"

"Um, why is he special?" asked Amy.

"He's in a wheelchair and has never had sex. He's 20, has no girlfriend, nobody wants him, he says and he just wants to get laid at least once before he dies, which his doctors have told him will be soon as he has an incurable, progressive muscle-wasting disease."

Normally Amy would have steered clear of a person like this, opting instead for the 'normal' guys, but after her recent discussion with Jessie she decided to take the opportunity offered; fate works in strange ways she thought.

"I could do it," she replied hesitantly.

Jessie looked at her and assessed the situation in the light of their conversation. Had she made such a huge change so quickly? Unlikely, she thought. She certainly seemed to want to make the change, but what if she regressed in the middle of the session and ended up hating the guy? Or worse, what if the guy's first time with a woman turned out to be a total disaster?

"Why don't we both do this," she suggested.

"We couldn't do that," replied Trish, "It would mean he'd have to pay double."

"Amy," Jessie began, "Are you willing to forego credits and bonuses for this guy? If so, so am I. Let's give him a freebie."

Amy agreed, and while Trish was firstly opposed to the idea because it would 'create a precedent', they talked her round before walking out to meet Gary, a great looking guy from the hips up, but his legs were withered and useless. Trish introduced them then left when she saw that everything was under control. Jessie collected drinks from the bar and they sat comfortably in the lounge.

"How long have you had this disease?" asked Jessie.

"I was born with it apparently, but at first it didn't affect me a great deal. It started in my feet so I had difficulty walking because I would lose my balance easily. My parents just thought I was clumsy. Then it became increasingly difficult for me to walk at all and after the doctors had done a large number of tests they diagnosed the problem. Gradually I lost feeling in my lower legs and my legs wasted away because they weren't used. Right now I have feeling in my hips but not in my thighs, so I really want to get laid to know what it's about before my pecker goes numb, as I think it probably will in the next few months or so. I've been told that once the numbness reaches my torso my muscles in my abdominal cavity will cease to function and I'll die, so I probably only have a year at the most left to live. However, I intend to make the most of that year or however long I have and when it's over, it's over. I'm quite resigned to dying earlier than most people, but I'd like to experience as much as possible first. It's amazing how philosophical and daring I've become now that longevity is not an option."

"That's really tragic," commented Amy, "It must be so hard to see older healthy people. Don't you get eaten up with envy and possibly even hatred that others have what you can never have?"

"No, not at all. I may have at the start, but what's the use? I can choose to be happy or not; I choose to be happy. There's simply no point in ruining what little I have of life by being morose about not having more. Enjoy each day as it comes is my main aim. Today has come, and I intend to enjoy it to the fullest with help from you lovely ladies."

"Well, I think you're really brave and have a wonderful attitude towards life," commented Jessie. "Now, how can we help you?"

"Well, I have masturbated but I've never been with a woman. So I'd really like it if you could please do whatever you think I'll enjoy. One thing I do want is to cum inside a woman; I want to feel what that's really like."

"That'll be no problem at all. We're used to that, although most men have use of their legs to push with. We may have to investigate some different techniques to see how that goes for you. I guess the first things are to undress you and get you onto a bed. Shall we go to my room?" asked Jessie.

"Yes, yours is bigger so there'd be more space for the wheelchair," agreed Amy.

Once in Jessie's room both girls stripped to their panties and allowed Gary to rub his hands over their bodies. He explored them both slowly and thoroughly, one at a time, ending by looking into each girl's eyes as he slipped his fingers into the elastic of their G string thong and pulled the flimsy garment to the floor. After that he felt between their legs for a short time, feeling their dampness and tasting them on his fingers.

Once he had finished this process for them both he was clearly very aroused. Amy and Jessie lifted him onto the bed and stripped him naked, exposing his withered legs and his well-built and muscled upper body from his exercise in propelling his wheelchair. They lay each side of him and caressed his body, kissing him all over but avoiding any contact with his hard cock that was swaying from side to side.

"My word, you are a big boy," teased Amy as she gently rolled him from side to side to make his cock sway more, "And look at that precum dribbling down as well. You are so horny, honey."

"Yes," replied Gary, his frustration rising to new heights, "Can't one of you just fuck me, please? I so desperately want to cum."

"First we need a condom," Jessie insisted, removing one from her drawer and rolling it onto Gary's cock. "It's my room so I'm going to be your first."

Jessie straddled Gary's hips and teased him still more, running his cock head between her dripping labia so he could feel her against his head. Then she positioned herself over him and, while watching him in the eyes, lowered herself onto him in one easy movement until she was sitting on his pelvis with his cock fully inside her.

Gary's face was a picture of pleasure and lust. He had held his breath as Jessie lowered herself and now he breathed out then took several quick panting breaths.

"Ooohhh, that feels marvellous," he said huskily, "Far better than wanking. Mmmm, fuck me darling."

Jessie wasted no time in carrying out his request. She moved back and forth for a bit, then raised and lowered herself, each time she lowered herself she ground her pussy against his pubic bone. Gary clasped her hips with his hands and encouraged and assisted with her back and forth motion, pushing them both to greater heights as their orgasms approached. The sensuality of the atmosphere along with Gary's newness to these erotic sensations ensured a quick release and after only a few minutes of this motion Gary tensed and held his breath as he spurted his cum into the condom at the end of Jessie's vagina.

Jessie felt the added warmth and began to move more rapidly, milking his cock with her practised vaginal muscles as she ground her clit against his hard bone and cock, then with a small cry, she came, resting forward on her arms over his body, her breasts brushing his chest as she continued to wriggle her hips to gain maximum stimulation. In a few moments she collapsed onto his upper body, kissing his lips and nuzzling his neck.

"Mmm, thank you, darling," she whispered into his ear, "That was fantastic."

"No, thank you, honey, thank you for giving me my first orgasm with a woman. That was soooo good."

"Well, lovebirds, it ain't over yet," said Amy. "You two looked so sexy that I had great difficulty in stopping myself from simply rubbing my clit till I came too. So now it must be my turn."

Jessie lifted herself off Gary and held the condom as she moved upwards, allowing his still semi-hard cock to pop out. She reached down and used a towel to catch his cum as she removed his condom from his cock and dried him.

"There you are, sweetie," she said to Amy, "He's all yours. May need a while to recuperate but I'm sure you'll manage to get him up for a second round."

"Thanks," replied Amy, "I hope you haven't drained him completely."

"No chance of that," interjected Gary, "When I masturbate I can cum several times each session, so I should be able to do even better than that with two sexy girls here to stimulate me."

Amy lay beside Gary and trailed her fingers lightly over his chest and abdomen, noticing his cock twitch as she approached it. With her other hand she held his balls gently, massaging, kneading and extending his scrotum downwards as she stimulated them. After a few minutes of this he had hardened considerably so she placed her mouth over his cock head and began licking around his corona with her tongue. Gary nearly left the bed; he closed his eyes, moaned through his pursed lips, rolled his head from side to side and writhed beneath Amy's still stroking hand. He was obviously enjoying himself. Gradually Amy increased the stimulation, taking more of his cock inside her mouth and watching Gary's increasing response. She didn't want him to cum too soon.

Jessie watched Amy apply her specialty to Gary and noted his response, about what she would have expected from a guy on his second ever sex with a woman. She didn't think he would last long at all so wasn't surprised when Amy stopped what she was doing to prevent his premature ejaculation.

"We don't want you cumming too soon now," she told him.