Mrs. O'Grady's Boarding House

"Yes, it often is better than with a man because women know what to do and how to stimulate each part of their bodies while some men have no idea at all. Do you want to do it again some time?"

"Oh yes please. Maybe with some toys next time perhaps? How often can a woman cum like that? I know guys run out after a while and need recuperation time, but do women also?"

"My, aren't we full of questions! Toys next time will be great, my room tomorrow perhaps? Women can keep on cumming for a long time, they really have no physical limits but can get a bit sore after a while. The most I've had in one session is five; it was wonderful but exhausting."

"Hmmm, perhaps sometime we can push ourselves to the limit to see if we can break your record," suggested Jessie with a grin, "I know I'd like to try."

"Yeah, maybe," replied Melissa noncommittally. "Anyway, it's dinner time almost, time for a shower together."

They showered in Jessie's ensuite then dressed for dinner. Clothing around the boarding house was usually scant and sexy; after all, when people made a living from enticing others to have sex and when they were only going to take off their clothes again in a short time, it seemed pointless over-dressing. So they both put on skimpy bras and short wrap around skirts, staying naked beneath the skirts. They then went downstairs to the dining room arm in arm.

The other girls in the dining room recognized the change in both attitude and demeanor immediately.

"Well, guess who's hitched up with each other," said Candy loudly to attract the attention of the others to the happy couple.

Jessie blushed and looked down but Melissa had formed relationships with several of the girls so smiled at the others and walked over to the buffet with Jessie.

"It's all in fun and you'll get used to it. Now that they know you've been initiated into the girls club you're likely to get a few more propositions. Enjoy."

They helped themselves to the delicious dinner and sat at a table with several other girls, some of whom knew that Jessie had had her first trick that day. They discussed how things went and swapped stories with each other while Jessie listened intently to see what she still had to experience.

After dinner the group split up, some had tricks, some to relax in the recreation room, while some returned to their bedrooms. Trish approached Jessie as she was a little at a loss to know what to do.

"I understand you've had an interesting and successful day," she said, "Jake seemed very happy with his experience and has told me he'll be asking for you again soon, and I hear that you've been initiated into the girls club. Welcome aboard. Nearly everyone here is a member so if you want company in bed just ask someone who's off duty. It's rare for anyone to be turned down. Also I'm pleased to see you've adapted so quickly to wearing very little; some newbies take weeks to discard non-essential clothing."

"Well, thanks for the praise. I'll certainly look forward to meeting Jake again and I really enjoyed my experience with Melissa so am very open to propositions from other girls' club members. Melissa told me she'll be introducing me to toys sometime soon."

"Yes, she's an expert in using toys, both on women and men. You couldn't learn from anyone better."

"That's great. So are you busy right now?"

Trish laughed. "Are you propositioning me?"

"Yes, I guess I am," replied Jessie, wondering if she'd made a big faux pas.

"Thank you, I would be delighted to join you in either of our rooms. Yours or mine?"

"You choose," replied Jessie, relieved at Trish's acceptance.

"Right, mine it is. Do you need anything from your room?"

"No, I'm fine, let's go."

Trish grabbed Jessie's arm and together they walked the short distance to Trish's suite, which was very similar to Jessie's. Once they entered, Trish shut and locked the door, then began kissing and caressing Jessie as they shuffled their way towards the bed. Once they reached it they collapsed onto it, still kissing, and began stripping each other, not a long task due to the few items of clothing each wore. Once they were naked they broke their kiss and looked at each other.

"Don't they hurt?" asked Jessie as she touched Trish's nipple rings, moving them gently.

"Not usually. They did when they went in and for the first couple of weeks, but now they only hurt if I or someone else twists them or pulls them hard. It's sort of a nice hurt though; I'm quite into pain."

"Oh, so I can pull them and you don't mind?"

"Yes, go ahead and start pulling on them. I'll tell you when to stop."

Jessie pulled on them both at once, watching as Trish's nipples elongated and the holes became larger and oval. Trish closed her eyes and a smile came to her face.

"Harder, darling, pull them harder please."

Jessie obliged and was soon pulling quite hard while Trish's smile had changed to more of a grimace and she'd gritted her teeth. After a little more she told Jessie that was enough, and Jessie released the rings gently.

"Ooohh, that hurt so good," said Trish. "Did you like playing with them?"

"Yes, it was strange but kinda fun. The strange part was that I could so easily cause you pain and that you seemed to enjoy it."

"Mmmm, yes, I did. Do you want to try stretching another ringed part?"

"Yes please."

Trish spread her legs wide and Jessie could see a small ring through Trish's clit hood. She touched it gingerly, afraid of hurting that sensitive area.

"Go on, grab it and pull. I'll tell you when to stop."

Jessie did just that and soon had the clit hood extended far out while Trish lay on her back on the bed and rolled her head from side to side, moaning in a combination of pain and pleasure. After a few minutes of this she told Jessie to stop, and again she lowered the ring gently back to its normal place.

"That makes me so hot and really gets my pussy flowing. Put your fingers inside and have a feel."

Jessie fed first one, then two, then three and finally four fingers into Trish's very wet tunnel, moving them back and forth as she watched Trish's face. After a few strokes Trish was pushing herself against Jessie's hand, seeking more pressure, more pleasure. On a whim Jessie used her thumb to move the clit hood ring, pushing it upwards, surprised when it moved completely off her clit leaving this relatively large organ fully exposed and vulnerable.

"In the drawer, please, there's a red clip. Put it on my clit."

Jessie used her other hand to open the drawer and retrieve the clip, then pressed it open and placed it on Trish's exposed clit, allowing it to close slowly. As it closed more and more she saw Trish's face grimacing and smiling at the same time. She continued to finger fuck her and after only a few more strokes she was pressing upwards against her hand, panting and moaning. Then, with no further warning, she came hard, giving a shrill, short scream as she went rigid, gripped the bed cover with both fists and her body began to convulse.

Jessie didn't know what to do so she continued finger fucking her while using her other hand to pull her nipple rings alternately. After what seemed like hours, Trish's body relaxed and she began breathing more easily. Jessie slowed then stopped her hand movements and watched as her friend and lover slowly recuperated from her intense orgasm.

"Whew, that was amazing," she said eventually. "What a great lover you are, darling Jessie."

Jessie kissed her and thanked her for the compliment.

"Now," said Trish propping herself up, "Your turn to cum. But first please take the clip off my clit, it's painful without the sexual arousal to go with it."

Jessie obliged, then Trish pushed her onto her back on the bed cover, kneeling between her knees.

"I wonder how we should stimulate you," she mused, "You have no rings to pull and your clit hood is still attached to your clit. You could have that freed if you wished, you know. Perhaps a few clips to begin with."

Trish found several clips in her drawer and after arousing Jessie some more with kissing, nipple and breast stimulation and two fingers inside her very wet tunnel, she slipped them onto her nipples. At first Jessie drew in her breath sharply but then rapidly became accustomed to the pain and pressure. Trish selected another clip and enlarged her clit by pulling and massaging it before she fitted the new clip to it.

"Aaarrgghh," yelled Jessie, then quickly bit her arm to stay silent as the clip did its work of causing her clit to engorge and send sexual stimulation coursing through her body. She'd never felt like this before. All she wanted, needed, was to be fucked and fucked and fucked, again and again until she was completely comatose.

"Is that OK?" asked Trish.

"I guess so," replied Jessie. "It hurt at first but it slowly gets better."

"Good. Let's proceed. I can see you're just aching to cum."

Trish put two fingers in her slippery tunnel again and moved them around, pulling sideways, stretching, widening, then she added a third finger, repeating the process, then added a fourth finger, pushing in as far as she could. She wriggled her fingers inside, stimulating, stretching still further, then she pulled partly out and placed her thumb against the palm of her hand and slowly pressed inwards, watching as her hand disappeared inside Jessie, watching Jessie's face as the realization that she was taking Trish's whole hand sank in. She stopped when her finger tips touched the end.

"How's it feel?" asked Trish.

"Enormous. But it doesn't hurt, it just feels like I'm so big and it's really sexy and nasty. It's the nastiest thing I've ever done."

"Right, so I can continue, OK?"

"Yes, please do," replied Jessie wondering what was next.

Trish began slowly closing her hand into a fist. Jessie felt the finger tips leave the end of her vagina and slowly her vagina expanded as Trish's fist tightened.

"Still OK?"

"Yes, I think so."

"Good, nearly finished."

Once she had made a tight fist inside Jessie's vagina, Trish began pushing in further, further, slowly to allow her vagina to expand to accommodate the size of her fist, until her hand was fully inside and the vaginal entrance muscles closed around her wrist.

"Well done, have a look at what this looks like."

Jessie propped herself up and looked between her legs. She couldn't see Trish's hand, only her wrist projecting from her vaginal entrance.

"Omigod! You've got your entire fist inside me. I'll be totally slack in future; guys' cocks will simply flop around in there. What have you done?"

"Shhh, it's fine. Your vagina is very elastic and will quickly resume its normal size. After all, babies pass through there, so a fist is not large at all. Now, are you ready to cum?"

"Oh yes, darling, I need to cum so badly," she replied, thoughts of the future being replaced by a horniness she had never felt before.

Trish started moving her fist in and out, slowly at first then faster, while she rubbed Jessie's clit with her other hand, back and forth. Jessie relaxed on the bed then began pushing upwards in time with the thrusts, moaning gently from arousal, then louder, moving faster, rolling her head from side to side, then she was there. Her body bucked against Trish's fist, which pushed it further inside, pressing hard against the end while Trish's other hand squeezed and pulled her elongated clit as Jessie thrashed about on the bed, gasping for breath.

Jessie's orgasm lasted several minutes, after which she slumped onto the covers, panting, unmoving as she recovered. Trish eased her fist out and lay beside her, cuddling her, kissing her. Gradually Jessie came back to full waking consciousness.

"Wow, that was something else," she said eventually, opening her eyes and gazing lovingly at Trish. "Absolutely wonderful. Thank you, sweetheart, thank you so much. Geez, have I learnt a lot today."

"You looked so wonderful cumming on my fist, sweetheart, absolutely adorable. I'm tired; will you stay with me tonight, darling?"

"Yes, of course."

The two exhausted lovers curled up on the bed with just a sheet over them on the warm night and were soon sound asleep.

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

Over the course of the next few weeks Jessie 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, so, she reasoned, why was anything else necessary? She shared her bed with many of the women in the 'boarding house' and also shared the beds of many of her new friends. She quickly gained a reputation as a strong reliable young woman who could deal firmly and diplomatically with difficult clients.

Thus it was that Trish assigned her a person who would be thought to fall into the 'difficult client' category. He had given his name as Mr Fitzgerald and had asked for someone who would understand his special needs. Trish immediately thought of Jessie and called her down.

"Hello Jessie," Mr Fitzgerald greeted her when she was introduced to him by Trish.

"Hello Mr Fitzgerald. I am very pleased to meet you," she replied, noting his apparent interest in her short skirt and low cut top. "How can I help you today?"

"Well, that's a long story," he replied. "Many years ago . . . "

"Look, it's not easy to talk in the foyer," interrupted Jessie, "Would you like to get a drink and then we can go to my room. It will be far more comfortable and private."

"Thank you, my dear, that would be lovely. I'll have a scotch and water thanks."

Jessie took him to the bar and ordered for him, telling Stefan, the barman, to put it on her tab and that she'd have a soft drink; she didn't want her instincts dulled by alcohol. Then she escorted Mr Fitzgerald up the stairs to her room. Once inside, she locked the door and they sat in her comfortable chairs sipping their drinks.

"Now, you were saying?" she prompted.

"Oh, yes, it's a long story. My wife of nearly 50 years passed away about six months ago. I've always had a strong sex drive and for most of our married life she took good care of my sexual needs. You will maintain absolute discretion, won't you? I'd hate word of this to get out to everyone, especially these days when there's so much social media around."

"Yes," Jessie reassured her, "Everything you say and do here is strictly confidential."

Mr Fitzgerald breathed a sigh of relief and continued his story.

"During the last few years of her life she found sex painful so we mainly focused on mutual masturbation, which we both found perfectly satisfactory. But since she passed, God rest her soul, I have become increasing sexually frustrated and I got to wondering whether the right girl would be able to stimulate me so I could have a last erection and make love in the normal way. I must explain, after our normal sex ceased I became less able to achieve an erection, so most of my orgasms occurred when my penis was soft." He looked away and the hung his head. "It's so difficult talking about my sexual problems with anyone, but I think you are probably very sensitive and can understand them without writing me off as just another impotent old man."

Jessie placed her hand on his knee reassuringly. "While I've never grown old yet, I know that time will come and I would hope that someone will be able to treat me as a real person with real needs when that time does come. I know that you're not simply an impotent old man and I assure you that I will do my very best to meet whatever needs you have. Please continue with your story."

"Thank you, my dear," he replied, placing his hand on hers, "I am so grateful that you have the time to listen to this old man. That really is my story. All I want is for my penis to stiffen as it used to and to once again feel it sliding inside the slippery vagina of a woman. That's all I want. Can you help me to achieve this please?"

"I'll do my absolute best to enable you to achieve your goal," replied Jessica, wondering what exactly she could do for what was possibly chronic erectile dysfunction, "What is your first name please? If we're to be lovers, it would be easier to use that than call you Mr Fitzgerald all the time."

"My given name is Claude. Yes, please call me Claude."

"Thank you, Claude. When you were younger, what things really turned you on? What did your wife do that made you become really hard and sexy?"

Claude thought for a few moments. "Mainly I enjoyed feeling her pussy. I really liked to stroke it, stroke the hair on it, touch her labia and run my fingers through her slit, feeling her juices start to flow. I think that, more than her playing with my penis, was the greatest turn on."

"So would you like to do that with me?"

"Oh yes please. Would you let me do that?"

"Of course. I would really enjoy you doing that for me. I would also enjoy you stroking my clitoris and playing with my nipples until I come to orgasm. Would you like to do that too?"

"Oh yes please, sweetie. It reminds me of all the fun we had on our honeymoon and the years afterwards before we had children. Once you have children, you know, your sex life drops off because your wife becomes a mother and very often you feel lonely because she has to spend so much time with the children. Just remember that when you get married and have children. I used to really enjoy sex but I was also working hard and was often tired. My wife used to want sex but I would reject her because I was tired from work. Oh how I regret those days; what a waste."

Jessie knew that he was becoming morose and that she had to bring him back to his former sexual enthusiasm.

"Would you like to undress me, Claude?"

Claude returned to the present situation quickly, looking over towards her young, nubile body and wanting to see more.

"Yes please," he replied.

Jessie stood in front of him and went into a role play, playing his wife as she thought it may have been in those early years of marriage. "Please, dear, would you remove my top for me. I feel so sexy and hot for you."

A smile crossed Claude's face as he reached up and began slowly unfastening her buttons. Once they were all undone, he stood and eased the top off her shoulders, noticing that she wasn't wearing a bra.

"Where's your bra?" he asked.

"I felt so sexy for you that I left it off. You like that?"

"Oh yes, that's so hot, sweetheart. Can I rub my hands over your breasts please?"

"Of course, darling, rub my breasts and squeeze my nipples just as you know I like. I want you so much, darling, please make love to me."

Claude began massaging Jessie's breasts, tweaking and squeezing her nipples, almost believing that this was his dear wife that he was loving.

"Mmm, yes, like that, honey, that's so nice. Here, let me take your shirt off, honey."

Jessie removed his tie, undid the buttons of Claude's shirt then slipped it off his shoulders and down his arms, rubbing her hands over his weak, sunken chest, a mere shadow of the man he must have once been. He continued to massage her breasts and then, after a few minutes, he wrapped his arms around her and hugged her to him, pressing her nipples against his chest. Jessie tilted her head back and they kissed gently and sexily, exploring each other's mouth with their tongues while continuing to caress each other's upper body.

After nearly ten minutes of this Jessie reached down and undid his belt, then undid the clip and zip on his trousers and eased them down his legs until they were around his ankles. Wordlessly she encouraged him to lift each foot in turn until he was free of his trousers. She then resumed the kiss and caress.