Mrs. O'Grady's Boarding House

"Ooohhh, Amy sweetheart, that was so wonderful. I certainly was getting close. So what now?"

Amy lay on her back and then instructed Gary how to position himself, asking Jessie to help if necessary.

"I want you straddling my body with your cock about level with my breasts," she told him.

He quickly used his powerful arms to get into position, moving his legs with his hands so they were supporting him a little and preventing him from overbalancing. He reached forwards and held Amy's shoulders for better balance.

"Right, darling, so what I'm going to do is to put some oil on my breasts then hold them together around your cock. You can then move back and forth by pushing and pulling my shoulders so you'll tit fuck me. Sound OK to you?"

"Sounds great to me," replied Gary as Jessie passed the oil to Amy and she spread it over her breasts and his cock. She then pressed her breasts together, sandwiching his cock between them. It didn't take long at all for Gary to work out the best way to move back and forth and he was soon fucking up a storm between Amy's breasts. After the oral stimulation and despite his recent orgasm, he quickly reached his climax and spurted his cum onto Amy's shoulders and neck while he arched backwards, his eyes closed and his breath coming in loud gasps as he experienced an intense release.

Once he again relaxed, Amy released her breasts and he rolled off her and onto the bed once more, lying beside Amy.

"Did you cum?" he asked.

"No, sweetie, I didn't, but that's OK. I don't need to cum every time."

"But I want you to," he replied. "How can I bring you off?"

"You could use your fingers," suggested Amy, "Or your tongue if you like."

"Mmm, I think I'll start with fingers then use my tongue."

With Jessie's assistance, Amy was soon spread widely and Gary learnt the intricate details of female anatomy, experimenting by gently rubbing oil onto her labia, into her vagina and finally oiling her clitoris, which caused Amy to mewl softly.

"The clit is very sensitive," instructed Jessie, "But after a while it can become numb if rubbed too long or hard. It's usually best to keep it for last after warming your lady up by caressing her labia and whole pussy area and, of course, by copious kissing of both sets of lips. Once she's hot to trot, then you can use your tongue and lips on her clit and lips. Just stay in tune with her and you'll get a sense of what she wants and what isn't working for her. You can also play with her breasts and nipples. Don't just concentrate on the nipples or they also may become numb, but include the whole breast. It's most important to take your time and be observant."

Gary began as instructed, fingering Amy gently, watching for her responses and changing the stimulation frequently. Amy writhed in pleasure, mewled when her arousal increased, gave small cries of pleasure when Gary squeezed her nipples, and almost came when he massaged her clit so beautifully. Gary was being extremely observant and stopped his clit stimulation just before the point of no return, leaving Amy frustrated and horny beyond words.

"Oh, darling, I need to cum, now," she told him, to which demand he replied by moving down until his mouth was over her pussy, his hands gently cupping her breasts as he rolled her nipples between his fingers, and he began to slowly, slowly lick the full length of her vulva.

"Oooohhhh, yes, yes, more, harder, I'm soooo close, darling, don't stop, ooohhh, yessss, make me cum, oooohhhh yes darling, like that, yes, yes, ooohhhh, I'M CUMMINGGGGG!!"

Amy's body thrashed about beneath Gary as he maintained his stimulation of her breasts and used his lips to suck her engorged clit hard into his mouth. For at least two minutes Amy thrashed about beneath him, gasping, panting, moaning, before slowly relaxing as he reduced the stimulation and lay with his head propped in his hands, watching her as she gradually regained her composure.

Once she was lying quietly, he kissed her tenderly. "Wow, you were really something, sweetheart," he told her, "It was fantastic to see you so aroused, enjoying your release so much, knowing I could give you that much pleasure."

She reached toward him and drew him down for another kiss. "What a great lover you are! Thank you, honey, that was fantastic."

"So what shall we do with you this time?" asked Jessie, reaching for Gary's rock hard cock. "You're certainly up for more. I was thinking, you mentioned you wanted to cum in a woman but when you made love with me you wore a condom, which removes a lot of the pleasure of cumming inside a woman's vagina. I guess that as I'm the only woman you've fucked so far, the chances of any disease is nil and as I'm on the pill, the chances of pregnancy are also almost nil. Would you like to use that huge cock in me bareback?"

Gary's face lit up with a radiant smile. "You'd let me do that?" he asked incredulously. "Yes please. That would be my dream come true."

"Right, so this time it's missionary so you'll have to do the work. Can't let you free ride too much or you'll get to like it."

Jessie lay on her back, legs apart, knees bent a little and Gary positioned himself over her, between her legs, his weight taken on his strong arms and his useless legs splayed on the sheet. Because of his upper body strength and reduced lower limb weight, he could balance there quite easily with his cock just resting at Jessie's entrance.

"When you're ready just push him in and move yourself forwards," instructed Jessie. "Amy, let him do it but intervene only if he obviously needs help."

Gary followed instructions and easily slid his bare cock into Jessie's drooling tunnel. He then lay on her briefly as he repositioned his elbows on the bed, then once again took his weight and began thrusting forward and withdrawing rhythmically.

"Well done," said Jessie, "You're fucking me all by yourself. But I will give you a hand and it will also feel better for us both as I'll be able to pull your hips tightly against mine, stimulating my clit and the base of your cock."

Jessie grabbed hold of both his ass cheeks and synchronized her movements with his to pull him against her as he pushed fully inside. They kept this motion going for quite a long time, Jessie holding off as long as possible to allow Gary a chance to cum in her first, a slightly longer process as he had just unloaded two doses of his cum in the past half hour.

Gary's breathing became more of a pant and Jessie felt him thrusting more vigorously inside her so knew he was approaching his third orgasm, his first bareback inside a woman. Jessie was also ready and felt she could no longer hold off the inevitable when, with a final hard thrust and a corresponding upward pull from Jessie, he closed his eyes and with a triumphant yell shot his potent sperm against the end of Jessie's vagina. The feel of the warm fluid pumping against her cervix drove Jessie to her own orgasm and she groaned in relief at the release she felt as she clutched Gary to her tightly as the lovers both came hard.

Amy watched them in awe at their simultaneous strong orgasms, her pussy feeling decidedly empty and neglected. She decided it was her turn once more to extract a final orgasm from Gary and to offer him one more of her own. She waited, slightly impatiently, for the two lovers to part. After a long time they did, Gary extracting his now soft cock from Jessie's vagina and watching as his white cum oozed from her opening. Amy saw her chance and gently moved Gary aside and lowered her mouth to Jessie's pussy where she licked Gary's juices as they ran over Jessie's skin, then sucked more from her, covering her entrance with her mouth. Once she could suck no more out, she sat back and licked her lips.

"Yummy," she said, looking at Gary, "Thank you. I love the taste of your cum. Now I want to extract some more from you." She looked at his cock and held it gently in her hand, noting that it had hardened considerably during the time she had been feasting on its juices. "Ooohhh, you're getting bigger. That's a good sign."

Amy once again stimulated Gary's cock with her mouth and in only a few short minutes it was hard and ready for action. She lay on her back as Jessie had done.

"Fuck me, loverboy, fuck me hard and long and push your delicious cum inside me, no condom needed."

Having already had practice, Gary positioned himself between Amy's legs and with very little ado was deep inside her love tunnel while she was pushing and pulling him, moving him like a human dildo as he stimulated every nerve inside her. She decided that this one was for her, and whether Gary came or not was not her problem. She just wanted to be fucked hard. Within a few minutes she was panting for breath from her exertions of pushing and pulling Gary, who was unable to thrust as hard as she would have liked. She felt like she was nearly there, really close. She closed her eyes, pulling harder, her arm muscles screaming from the unfamiliar exercise, a few more pulls, two more, one more, then . . .

"AAAARRRRGGGGHHHH!!" screamed Amy as her orgasm took over her body, causing her vagina to contract, her body to writhe and shudder as massive sensations coursed through her.

While Gary had been slowly approaching another climax, Amy's sudden and unexpected orgasm took him completely by surprise. Her clasping, clenching vagina tightened around his cock and caused him to thrust faster and harder than he thought possible into Amy as she lay beneath him writhing in ecstasy. He felt his juices flowing, pouring through his urethra into the end of Amy's vagina at the same time as the sensations of his ecstatic release washed through him, causing him to stop, tense, feel his cock pulsing squirt after squirt of semen into Amy, then he relaxed, his arms weak at last, he collapsed onto Amy and lay there for a few seconds, recovering, then lifted himself once more as she began to show signs of distress from his weight.

The trio cleaned up and showered together, once Jessie had sucked Amy dry, then dressed and returned to the lounge, where they had a group hug.

"I do hope we can do that again," said Amy, "That was so much fun."

"Well, thank you both for that amazing experience," said Gary, "I just don't know what to say except thank you, thank you, thank you. I really never expected that at all; it was awesome."

"I certainly enjoyed it too. Thank you, Gary, you're a wonderful person and exceptional lover. Any woman who consented to be your partner would be very fortunate indeed," said Jessie.

"Thank you both again. I'll be back sometime; count on it," replied Gary as he turned and propelled himself to the door.

Three months passed before they heard from Gary again. The email that Jessie received said that news wasn't good and that he was confined to bed in a hospital.

'The news is all bad I'm sorry to say. The nerve damage has progressed quickly to above my hips now, so I'm on life support as my kidneys are no longer working. I have no feeling in my cock either, so that would be no use to you two lovely ladies. I doubt that I have long to live but for that brief period I will remember the afternoon we spent together with joy, love and gratitude. Go well in this life and enjoy it while you have it.

Love, Gary'

Two more weeks passed with no news and eventually Jessie phoned the hospital.

"Good afternoon, my name's Jessie and I'm friends with a guy by the name of Gary. Sorry, I don't know his family name. I do know he's suffering from a muscle wasting disease and he was on life support last I heard. I just wondered if he was able to have visitors please."

"I'm really sorry, Jessie. I do know the man you're talking about but he passed away a few days ago. You must have been one of the people he loved dearly and I'm so pleased you phoned because it solves a mystery for us, at least part of it. Do you know anyone by the name of Amy?"

"Yes, she's a friend of mine and also of Gary's," replied Jessie.

"That's great; the mystery is solved. Gary's last words to the nurses were 'Tell Jessie and Amy thank you and I love them both.' We had no idea how to try to find you so thank you for calling. Is there anything else I can help you with?"

"No. nothing thank you. Thank you very much for the message. It means a lot. Goodbye."

"Goodbye, Jessie."

Jessie found Amy and they went to Jessie's room, where it had all started. Jessie passed on Gary's last message and the two women hugged each other and wept tears of sadness for Gary's passing, tears of frustration that life can be so cruel as to take such wonderful people so early, and tears of joy and gratitude for having known Gary and for having been able to grant him one of his final wishes and help him experience life more fully and sensually.

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

Life progressed well for Jessie over the first year in the 'boarding house'. She found that she enjoyed almost all aspects of sexual activity with both men and women, her only reservation being anal sex as she found it almost impossible to relax sufficiently and she didn't enjoy the pain. She also saw no point in it; she had a perfectly good vagina for men to use, and women also if they used the right toys, why was anything else necessary, she reasoned. She shared her bed with many of the women in the 'boarding house' and also shared their beds on numerous occasions.

She easily met and usually exceeded her weekly quota of four men so she frequently received bonuses and was able to save for the first time in her life. She established a regular clientele, including a young guy named Jake, who revisited her from time to time, each time becoming more adventurous as the sex became more enjoyable. After several weeks as they lay on the bed in love's afterglow, she questioned him about his visits while he was obviously married, based on him wearing a wedding ring.

Jake was quiet for several minutes and closed his eyes as though in pain, then he looked Jessie in the eye.

"You've become a good friend and so you deserve the truth, as far as I know it myself. Yes, I am married, at least I hope I still am, to a beautiful, talented woman who I love dearly. Her name is Celia. She is or was, I don't know which, an award-winning free-lance photographer who went to the Middle East several years ago. To begin with she would email me daily but after a few weeks these emails stopped and mine to her went unanswered. I tried to contact her through various embassies but to no avail; nobody had heard from her or knew where she was. It was suggested that she could have been kidnapped and sold into slavery, but I have no idea if that happened and I don't even know if I hope it did and somewhere she's still alive, or whether I hope she was spared that fate. However, I am a man, still young, have needs and I have visited Mrs O'Gs regularly for the past eighteen months. Until you arrived, I was assigned to several different young women, but you're different, it seems, and I must confess that I feel that I've fallen in love with you. I hope you don't mind me telling you that."

"Oh you poor darling," said Jessie once he paused, stroking his head gently. "I do hope she's OK and will return to you when she can."

"No, I don't think she can and it's very likely that she'll never return, that I'll never see her again. According to the authorities, I have to wait another few months and then I am able to dissolve the marriage. I was going to wait till then before I mentioned this, but as you brought the subject up, I'll continue now. It's as good a time as any. Over the past few weeks I find I've fallen in love with you. In many ways you are similar to Celia both in looks, attitude and sexuality. It's uncanny really but these similarities are probably what's enabled me to fall for you so easily and completely. I want to be married to someone who's here, not gallivanting around the planet, but, of course, I don't want to limit my wife in what she chooses to do. I also want children, a desire which was the only sticking point in our otherwise perfect marriage as Celia was adamant that she didn't want to be tied down by kids. So once I was free to remarry, I was going to find out your attitude towards having children and then propose to you. But this has sort of pushed things along a little. So first question, do you want to have children?"

Now it was Jessie's turn to hesitate. After a few moments she replied. "I don't know; it's something I haven't thought about. I'm certainly willing to have children, with the right man of course, so yes, I guess I want children," she concluded, feeling her maternal instinct rising.

"Ok, so that's the first hurdle. I just wonder myself if I'm ready to remarry or whether Celia's ghost would come between us. Maybe what you could think about would be if I was to propose to you, would you accept? That way we could both know whether it was a possibility or just a dream."

Jessie could hardly believe her ears. Here was her client all but proposing marriage to his hooker. She tried to envisage life as a married woman, living in a suburban house, raising several children, her wanderlust, freedom, joie de vivre limited while her husband went off and enjoyed himself in the wide world beyond the back door. She couldn't picture herself in that scenario.

But then she saw herself many years from now, older, her beauty faded, her body wasted from too many lovers, too much sex, with nothing permanent to hold onto. She pictured herself alone in a world in which she no longer fitted, her friends gone. She didn't like this picture.

She had always enjoyed new experiences, some as they occurred, others in retrospect because that was one experience she could now choose not to have. Marriage; hmmm, she thought, another new experience, but one to which she knew she would feel committed. Commitment, hmmm, did she want that? Could she do commitment? Perhaps there was only one way to find out.

And then there would be expectations of children, no doubt. Did she want children? Horrible, messy, pooey brats, maybe, or cute, cuddly adorable little people. She realized again that it was her choice how she saw them. Did she have the parenting skills needed to raise responsible human beings in this troubled world? All she knew was how to be a hooker, how to please a man, hmmm, how to negotiate deals, how to make people feel great, how to encourage people to go higher, better. Maybe those skills were all transferable to parenting. She rolled around in her head the idea of being called 'Mommy' by sweet little voices from children she loved more than life itself. She wanted this, wanted the challenges, the joys and, yes she admitted to herself, the inevitable heartaches.

After a lengthy silence of contemplation of this possible radicle change in her situation, Jessie replied.

"I have never thought the thoughts I've just thought," she began, "But in the last few moments I've looked at my life, at my values, at what I really want in life, and the answer is 'yes' to everything. If Celia does not return and if you do get your marriage dissolved and you are free to remarry and you do want to marry me and have children, the answer will be 'yes', darling."

Jake took her in his arms, pressed his now sated body against hers and they kissed long and deeply, wordlessly. At length they broke their kiss and he looked at her, still silent, then replied.

"Thank you, Jessie. I'm suddenly a much happier man. I now have a future to look forward to instead of the emptiness and loneliness I had anticipated. I'll let you know what happens. I love you completely and want to spend as much time with you as possible so I'll keep booking you as regularly as I can."

Jessie was a little confused. Did he really think she was committed to living here? Why couldn't they live together now and get married later? Did he have some old fashioned idea about having to be married before they lived together, but it was fine to fuck hookers?