May

Jack was in his last term at University before his finals at the end of May. Easter had been early this year. His mum, Jean, had asked her friend May if Jack could stay with her Monday to Friday for the last term as her Town House was a two-minute walk from the University. Jack had a fifty-minute drive to it then another fifty-minute drive home in the evening. Jack was comfortable with this as it gave him a lot of time for the critical revision he had to do. May and Jean were both doctors and had met at University. May's daughter Mags was also a doctor, but she was doing a year's internship in an American hospital.

Jack was staying with May and Tim, her husband. May was a lovely woman tall and curvy with a beautiful smile. Jack was not sure of Tim, he was a respected Architect and had won numerous awards. He was six inches smaller than May. Jean had told Jack that she found him a little effeminate which probably came from his artistic side. Jack was now in his second week at May's and had got himself into a routine. May served breakfast at eight. Tim left the house seven-thirty for his office. His secretary made breakfast for him. Dinner was served at six-thirty. After dinner, Tim went to his studio he had in the house where he would work. They had separate bedrooms.

After dinner in the early days, Jack went to his bedroom to study. There was an excellent Internet connection in the house, far faster than his connection at home. Every night he would Skype his mum. She was alone and didn't socialise much. His dad had died of cancer five years ago. He was a doctor too. He was a Urologist and had invented several medical instruments that were sold all over the world. He would spend ten minutes every day on Skype with his mum. She enjoyed chatting, and so did he. They talked about general things, and he would also look forward to his dinner on Friday night. Jean was an excellent cook.

Jack was staying in Mags room. May and he shared the same bathroom; there were connecting doors to each bedroom. Jack went to the bathroom just after ten one evening. May's connecting door was ajar. He could see May lying on top of her bed in the dressing room mirror. She was naked, and her legs were spread wide open. She had the perfect vulva that he had ever seen. Her cunt slit was perfect, swollen and smooth. She was fingering her cunt and easily taking four fingers. She had an orgasm then started to fist herself with a powerful rhythm. She was working her cunt. She said as she fisted herself, "Jack, I want your cock. I need your cock so much. I haven't had a cock for so long. Give it to me hard and deep in any hole that you want. I want to be your cum slut. Spray your spunk on my big tits, on my cunt and in my mouth. I need your spunk."

Jack couldn't believe what he was hearing. He had taken pictures and a short video on his phone of her playing. His massive cock was now rock hard. May then had a massive climax. She was shaking with it. The squelching sounds coming from her cunt were deafening. She regained her composure then lifted a pink thong from the floor and smelt it. She then smiled and used the thong to wipe her cunt juices from her cunt. A minute later the thong was dripping with her cunt juices. She then got her smartphone and called a preset number. She had the phone on speaker, she said, "My sissy husband is going to enjoy his supper tonight. I will now leave my soiled thong outside your bedroom door. I am getting very horny the more that I am around Jack."

Tim replied, "I would love to watch him fuck you. You know that this arouses me. Can you arrange this soon?"

May replied, "Do not rush me. I will do this in my time."

She hung up then took the dripping thong to his bedroom door. Jack then finished in the bathroom and went to his bedroom; he left his connecting bathroom door open. As he left the bathroom, he opened the laundry basket there were several pairs of pink silk thongs there. He took a pair then went to his bedroom. He studied the pictures and video he had taken. May had a magnificent body. Her tits were huge and didn't sag. She was the same age as his mum; he wondered if he could get any information from her. He then wanted and had a massive climax and filled the thong with hot cum. He took the drenched thong and left it not inside the laundry basket but on top of the lid. He was leaving a message.

He went back to his bed, leaving the connecting door open. He got into bed and left the bedside light on. He heard May going into the bathroom, he heard her peeing, then washing her hands. He heard her sniffing something then heard her say, "His cum is so sweet."

He pretended he was sleeping. May came into his bedroom and put his bedside light off. She left both the connecting doors open and went to her bed. In bed she phoned Tim on speaker phone, she said, "I hope that you enjoyed your supper. I want you to stay at your club for the next two nights. I want to spend time with Jack. Pack a suitcase for yourself, and I don't want to see you until Friday evening."

Tim replied, "I will pack the suitcase now. I will not contact you. I hope that you will be successful. I licked your thong clean tonight, thank you for thinking of me."

Jack's head was spinning, he had so many questions, and he needed answers. He was restless in bed but soon was in a deep sleep. He awoke the next morning just after seven. He heard May in the shower and was tempted to go into the bathroom but waited until she had finished showering. On entering the bathroom, the first thing that he noticed was that the thong was neatly placed on top of the laundry basket. There were several stains on it, but all his creamy cum had been licked off it. This aroused him. He shaved, showered and dressed then went downstairs to the kitchen.

May was preparing breakfast; she was wearing an apron to protect her blouse and skirt. She looked happy, and her voluptuous figure looked superb. Jack thought of the pictures he had of her from last night and would look at them later. When she saw Jack, she smiled warmly at him then came over and took him in her arms. Jack felt the weight of her massive breasts on his chest then push of her pussy against his leg. May said, "Thank you for the delicious supper that you left for me last night. I enjoyed every drop of it. I am looking forward to tasting more. I have arranged for my sissy husband to stay in his club until Friday, this will give us time to get to know each other. I woke up this morning with a craving for two things, firstly your cock and secondly a hot Indian curry. Would you like it, if tonight we stayed in and got to know each other and we ordered an Indian takeaway?"

They kissed passionately then Jack said, "I've no problem with what you suggest, I wanted to join you in the shower this morning, perhaps we can do that tomorrow morning. My last lecture finishes at three-thirty this afternoon, so I will be here shortly after that. What exactly do you mean when you call Tim your sissy husband?"

May laughed then said, "I'm more interested in getting to know you better. Tim is very effeminate, I have had to accept a lot from Tim. He lives in his world, and I live in mine, sometimes our paths cross. Tim is a cross-dresser, he loves to dress in lady's underwear. I gave him medication for breast enlargement, he has now a B cup, and this makes him very happy. He gets aroused when I humiliate him. The only thing that we both have in common is that we both are cum sluts. I so enjoyed tasting your sweet cum last night. Tim is my cuckold sissy cross-dressing husband. I am not a faithful wife. He loves to watch me being fucked then licking my cunt clean. Tim is unimportant to us at this moment. I will be prepared for you this afternoon."

They had breakfast. They kissed then Jack left for his first lecture. He had a free hour at eleven, so he went to the library to do some research. Just after eleven, his phone beeped, he had a message from his mum which read, "Darling, I am going shopping with Dot this afternoon. She is quite depressed as it was a year today that she lost her husband. She has invited me to her new apartment for dinner. I have decided to stay over with her as we will be drinking. She has discovered a new boutique which has some fabulous outfits and lingerie. I need to change my wardrobe as most of my clothes are over fifteen years old. Sadly, we won't be able to Skype this evening unless I take my laptop with me. I don't know how to do it on my phone. Hope all is going well with you. We can Skype on Thursday, and I will see you on Friday. All my love, mum xx."

Jack thought of Dot's looking glass figure. She was a doctor too and had studied with May and his mum. Jack then realised that he was now attracted to older mature women. He thought of Dot and his mum's big tits and smiled. Jack replied, "No problem, you should do that and buy lots of clothes. Dot has excellent taste, let her advise you on what to buy. You have a fantastic figure, and you should do more to show it off. Kay called Tim her sissy husband last night. There's something strange about him. After dinner, he goes straight to his room. Kay has her bedroom. I think that it's a strange marriage. Thinking about you too, all my love, Jack xx."

Jean's reply read, "Darling, thank you for the compliment; I will try and show my figure off more for you. Tim is funny; I believe that he likes to dress in women's clothes. When May was pregnant with Mags, she stopped having penetrative sex with Tim. She told me that he has a tiny cock and it did nothing for her. I believe that the only sex they have had for years is oral. I didn't have that problem as your father was a stallion. How I miss the kissing and touching. I can relate to how Dot's feeling and I agree with you that she has excellent taste, though sometimes it is a bit risqué. If I have any doubts about any clothing, then I will WhatsApp you some pictures of it. Don't worry about Tim; he is strange but harmless. All my love, mum xx."

He replied, "Mum, thank you for your honesty. I can't believe that we are having a frank conversation about sex, but I do believe that's the way it should be between us. I want to be honest with you. I think May wants to have sex with me. She was all over me this morning. She has told Tim to spend the next couple of nights at his club as she wants to spend some time getting to know me. I am staying with her because of your friendship with her, and I don't want to abuse that. I am attracted to her physically, and I believe that she is attracted to me. Are you comfortable if I fuck her? Your Jack xx."

Jean's reply read, "Darling, May loves to be fucked, in my heart of hearts I was hoping this would happen. May is quite complex sexually. She loves to be dominant with Tim, and she loves to be submissive when she is with someone she wants good sex with. She loves it in every hole, and she loves it deep and hard. Compliment her on her body; she has an excellent body. She has a massive clit; it is like a little cock. Suck on that as you finger fuck her then her cunt will soon be dripping. I want to be honest with you. I am bisexual though I haven't been with a man since your father died. I have been with May and Dot and a couple of other ladies."

"That's how I get my relief. Both May and Dot give excellent oral; I am looking forward to having Dot tonight. The beauty is that we are all clean, no nasty STDs are lurking around. My advice to you is be dominant with May, treat her like a slut, and she will give you a great fuck. I am thinking about you. I will send you some pictures of anything risqué that I may buy. I am looking forward to spending the weekend with you as I am sure a lot of nice things will happen. Message me tomorrow and let me know what happened tonight. I love you, mum xx."