The Challenge

George kissed her, "Option one, I need to taste you. I could see how aroused you were when I was being dressed. I want to eat you until you can't cum no more. Once we're both sated we can enjoy slowly playing this new game."

He pulled her into a loving kiss and they headed to the bedroom. He stopped her going to clean herself up, "I want to taste you as you are." He stripped her clothing, kissing down her neck, spending a lot of time on her breasts and nipples. He felt her react as she had done when she came from just breast play. It seldom happened but sometimes there were triggers and it appeared today was one. He kept teasing, twisting, biting and caressing her breasts, becoming more forceful. Debbie was moaning, "George, this is great. I'm thinking of you and me in matching lingerie playing with each other. Our breasts together. I can feel your nipples. I'm going to cum!" She rose from the mattress offering him her boobs as she came.

George continued down to her bare pussy and began slowly teasing her lips, down and around her perineum and bum hole before going back up towards her clit. "George, this is amazing. We'll have to remove your hair for you to understand how this is affecting me. Your pantie clad pussy rubbing my pantie clad pussy will be sensational. I love you."

George couldn't reply as he was almost drowning. Very soon he saw Debbie's pussy change to the deeper red which showed she was cumming. Her breathing was becoming rapid and she was moaning in pleasure. Her hips snapped from the mattress and almost threw him off the bed as she came. He let her come down as he continued to lightly caress her not so sensitive parts.

She pulled him up, "I love you, you gorgeous man. I'll never tire of you eating me out but I need a good fucking."

George was only too happy to slip his cock into her. It was sizzling. She set the tempo starting at a brisk trot before speeding up to a gallop. Neither lasted long. They cuddled.

Debbie said, "Let's have lunch and then play with our new toys."

Soon they were back in bed. Debbie had helped George put on his suspenders. As she smoothed the pantie over his cock it swelled. He was surprised to feel his own nipples react as she played with the breast forms. He hadn't expected them to do that. When he was dressed, Debbie laid back and lifted her legs exposing her bum. George had the lube ready but still played with her to get her to relax. It took a few minutes but when he saw she was in a happy place, he eased the plug into her bum. He took it slowly watching her reaction. He saw her smile as she looked at him. Her pussy was awash. He stopped to lick it clean in case it interfered with the lube, at least he told himself that. Once it was fully inserted he began to attack her pussy with his tongue and fingers.

The more George tongued her the more vocal Debbie became. "George this is so good. I never expected this. I'm going to cum and cum. I feel full and wired up." She was breathing very hard. Her eyes were showing signs of glazing over. Her hips were lifting from the mattress. George just licked and licked. His fingers found her "G" spot and she came within moments. He kept on going giving her no respite so soon another one came over her. "George fuck me, I need you in me, hold me, love me."

He did as he was asked as his cock had been demanding it for some time. He felt the plug as he entered and was grateful for the advice. Debbie pussy was always tight but somehow it seemed smaller. He began a little gentle rocking motion until he was sure he wasn't hurting her. She did tell him by grabbing him and shouting, "Fuck me hard, I'm cumming!"

He did, he rode her hard through her orgasm and kept riding her hard as another overcame her. Soon he realised he was in trouble as his cock was expanding and erupted just as she came again. He collapsed onto her. Neither could talk as they gasped for breath.

Finally, they parted and George lay beside her. "Wow Debs, that was something else."

Debbie was cradling his face, "George, it was fantastic. I was so turned on by you dressed like that and the sensation in my bum and pussy were so extraordinary, I couldn't control my orgasms. They decided when they came. They were so powerful as was your cock. I could feel every millimetre of him. I'd love another go but I don't think I can, not today anyway.

"I love you so much. What a great husband you are, open to try new things with me. I only hope I can be there for you for more things."

George spoke softly, "This month and really since the pool party has been all I have ever desired. I'm sure we bounced well over our preconceived boundaries. I never imagined anything like this but it was amazing. We'll need to speak fully about those but that will probably have to wait until love month is over. I wouldn't trade you for anyone. I love you, my sexy soulmate!"

Debbie laughed, "You weren't tempted last night with any of the other girls?"

It was George's turn to laugh, "You told me the boundaries and I agree with you. I did cum when you told me about that bloody poker game with friends but while they are all lovely, it's you I love and who I want."

He kissed her and they fell asleep cuddled in a big wet patch.

Day 27; - Monday -Carole - Doctor

Ron arrived home from work. He was a bit sad that he had had to return to the office as that sexy secretary certainly made his day. He thought about this week. It was coming to the end of the month and if he were honest, he didn't think he could survive if Carole was as energetic as yesterday. He hoped tonight would be a single cumming, like Wednesday's had become.

As he entered he saw a note with instructions. He was to shower and use the provided robe, make his way to the second door on the right. He was to knock three times and wait to be called in.

Ron did as he was asked. He was surprised to find a red satin robe in his size. It came to his mid-thigh. The sensation on his skin was arousing. They had played with him wearing lingerie a couple of times in the past but this month, Carole had dressed him in bra, suspenders and panties a couple of times before fucking him senseless. He had loved the contrasting sensations on his skin.

He knocked on the door and was invited in. There was a red headed doctor whose breasts certainly filled her blue scrubs. The V showed very interesting breasts which had his cock was trying to get out from the robe to see for himself.

The doctor spoke, "Mr Evans or would you prefer I call you Ron? Your wife has informed us you were feeling slightly under the weather, muscle aches, lack of sleep, a bit less interested in sex with her. Is this true?"

Ron smiled, "Call me Ron, please. I wouldn't say it's not true but I wouldn't state it like that. I certainly have muscle aches but this month I have been involved in a lot of physical exertions. I accept my sleep pattern has been more difficult due to the physical exertions but I do sleep very soundly, maybe not eight hours but certainly between five and six if not more.

"My wife is the love of my life and our sex life is great. I suppose this month it's been restricted to a Saturday due to our work schedules but I'm not less interested, just the contrary, I want to make love to her more."

"I'm Doctor Venus. I'll examine you and attempt to find a cause for those symptoms. I know you say you don't have them but men are rarely honest about their health. Lie down on the examination couch, please."

Doctor Venus examined his eyes, his nose and his mouth. She said, "You don't have obvious signs of anaemia or any infection." She opened the robe as she listened to his heart. He jumped, she hadn't warmed the stethoscope. She used her fingers to examine his breasts and smiled, "While your heart rate is slightly up, there are no obvious signs of lumps in your breasts."

She continued to check his armpits and down his arms to check his nails. He had never had a doctor do that so lightly it caused his cock to expand. She checked his feet and moved up his legs until she was at his groin.

She smiled and licked her lips, "I can see your penis appears to be healthy but I do need to take a sample. I'll do that after I've examined your prostrate."

She put on latex gloves and added lube. She had him lie on his side facing away from her allowing access to his anus. He felt the lube and a finger entering his bum. Whatever it was doing, his cock was waving. The sensation almost causing him to cum. He moaned in pleasure.

Doctor Venus laughed, "Some men love a good prostrate exam and others are so scared. This will help me get a sample quicker. If you remove your robe and turn over, I'll start with a massage as you are very tense. This may be a symptom of whatever you have."

For the next thirty-five minutes Doctor Venus massaged his head, back and legs. She had him turn over and she did his face, chest, arms and legs. He felt some lube being used on his cock as she wanked him. From being so relaxed, he felt stiff. He could see down that V to those breasts. It certainly helped his erection. Her hands not only wanked him but the other one caressed his balls and bum. As his body began to rise to her, he felt a finger in his bum and that prostrate being rolled. He came and came. When he looked at her he saw she had collected it in a dish.

Doctor Venus cleaned him before saying, "It looks like you are not producing as much sperm as normal. It may be tiredness or diet. If you go home, I'll instruct your wife on a meal for you. I'd suggest an early night but no further sex today. Once I have the analysis, I'll let you know if we need to add any medication but I think it will improve over the next few weeks."

Ron left the doctor's room and sat in his living room. Soon he smelt his dinner being cooked. Carole shouted him through, "Ron, I've made you steak as Dr Venus suggested you needed more iron.. There is some spinach as well." She kissed him as she stroked his chest through his robe. His cock started to revive. Carole looked at him and said, "Dr Venus said you need a cuddle tonight. No sex so Mr Happy will have to wait until the right time."

Day 28 Tuesday - Babs - pegging (crossdressing alert)

Bob arrived home and was surprised not to find Babs there. As he went to the bedroom he was shocked to find a woman's outfit lying on the bed. He had agreed to wear some lingerie for Babs and they had both loved it. When they had gone shopping, he was blindsided when she took him into a lady's fashion store. He had not thought why until she asked an assistant to measure him. He now had three sets of lingerie in his size with some extra knickers. She had bought him some nighties and a couple of dresses. One was on the bed. There was an envelope lying on it. He read the instructions. This evening was going to take him well beyond his comfort zone. He knew Babs had breached hers many times this month, now it was his turn to fulfil one of her fantasies.

He entered the shower and prepared himself as directed. Once he was hair free, he washed and cleaned himself thoroughly. After drying himself, he dressed in the lingerie. He had to admit he loved the sensation against his skin. He put in the breast forms and was amazed at the cleavage he had. He pulled on the dress and struggled with the rear zip but eventually managed. Now he put on the wig. He almost didn't recognise himself as the blond hair was so different to his brown. It came to just beyond his shoulders. He finished putting on the red lipstick. He was a bit wobbly as he put the heels on. They had a two-and-a-half-inch heel. He waited in the living room for the next stage.

Right at the time which had been in the letter, there was a knock on the door. Bob or rather Roberta, answered it. She was faced by a butch woman who stood tall in high heels. She was wearing a man's suit but it couldn't contain those magnificent breasts. The hair was slicked back and parted like a man's. The blue eyes stared at her.

She smiled, "Hello Roberta, your photograph doesn't do you justice. Once I saw you on the site, I knew I had to have you. I love to play with lesbian virgins, not to ravish but to make love with so they will remember with enjoyment their first time. I'll make sure you love everything I do to turn you on. You'll be a fully-fledged lesbian when I've finished with you."

She/he came in and kissed Roberta passionately. Roberta melted in her arms she was so overcome by the kiss. She parted and smiled, "I see you have your strap-on on already. I love it. I'm sure you will too." Roberta eyes opened wide but all that did was to get her another kiss.

They were making out on the settee and Roberta was feeling conscious of how her breasts were reacting to another woman playing with them. It didn't stop her from experiencing those lovely breasts from her companion for the evening. The name in the reply to her advert was Eve. She had added, "It's not my real name but Eve was the first and I'll be your first!"

Roberta was shocked when the door went again. Eve stood up and said, "I've ordered a takeaway. You can't make love on an empty stomach." Roberta relaxed as Eve answered the door.

They ate the Chinese meal in the kitchen, offering each bits and kissing each other's lips to taste the sauce. Each time Eve had a comment which had Roberta's strap-on asking to be played with. They took their wine into the living room where they talked some more as Eve explored Roberta's body. Not that Roberta was reticent in playing with Eve's. She found that Eve had no underwear on. Her bare pussy was flooding.

Eventually Eve suggested they retire to the bedroom to make love. She was going to blow Roberta's mind. In the bedroom, Eve kissed Roberta softly but she could feel the passion. Roberta felt her dress being slowly unzipped. Eve's hand on her back sent goosebumps through her. Soon the dress was on the floor. Eve looked appreciatively at Roberta.

She held Roberta's face and kissed her again and again. "Roberta you look amazing. The black silk lingerie enhances you so much. I love you chose that for your first time. I'm loving the size of your strap-on. Lie on the bed and I'll show you me."

Roberta watched carefully as Eve took off her suit. She had many man mannerisms and when she was naked, she looked like a man about to ravage his prey. She leaned over, "Once I've sated myself on your strap-on, I'll show you how to please a woman." Eve kissed down Roberta's breasts to her panties before taking them off. She added, "I love a strap-on which has balls and can cum in me."

Eve took Roberta's strap-on into her mouth to lubricate it she said. Roberta did enjoy this. Before she knew it, Eve was on her strap-on and she was riding her so strongly, Roberta was soon bucking to join her as they raced to an orgasm. Eve won but only just. She sank onto Roberta. After recovering for a few minutes, she spoke, her awe, clear in her voice, "Wow! Roberta for your first time with a woman, you were amazing. Now I'll blow your mind. Let's lie together and I'll instruct as to how to please a woman."

Roberta moved onto her side, facing Eve. Eve said, "Just follow me, do what I do."

She kissed Roberta who reciprocated. Eve took her breasts and lightly caressed them in their bra. Roberta took Eve's breasts and lightly caressed them.. Both were moaning softly as their arousal started to rise. As Eve moved down Roberta she had her move down with her. As Roberta came to her pussy, Eve began kissing along the perineum and her pussy lips. Roberta gasped but did the same. She tasted their joint cum. Eve was moaning loudly now. Roberta was glad she was able to do this to another woman.

Roberta's eyes opened when she felt Eve rim her. She moved her head so her tongue was rimming Eve. Eve moved back to Roberta's lips and clit which elicited a loud moan of pleasure from Roberta.

Roberta felt Eve move and was surprised when Eve made her move onto her back. Eve moved until she was between Roberta's legs. She lifted her legs and said, "Now, it's your turn to experience a strap-on for the first time."

Roberta felt something against her "pussy" as it slowly penetrated her. Somehow Eve had put a strap-on on and lubed her while playing with her. Eve spoke softly, "I'm glad I brought a strap-on the same size as yours. It is more than a bit bigger than normal. I hope you like it."

Eve slowly rocked easing back and forth until Roberta was moaning in pleasure. Roberta spoke softly, her arousal evident, "I never expected this." Eve smiled and kissed her love passionately as she began to fuck her to an orgasm. Slowly she allowed Roberta to feel the power behind those thrusts. When Roberta started lifting her bum to help her plough deeper, she knew she had overcome her fear.

Eve was beginning to rise to her own orgasm as the dildo was in her pussy as well. She was trying to match Roberta's as she wanted her to cum first. She was anticipating their first ever mutual lesbian orgasm. She felt Roberta's strap-on twitching as it ran over her stomach. She loved the feel of Roberta's breasts on her. The black silk lingerie was driving her senses wild.

Roberta began to stammer, to moan incoherently as she approached her orgasm. Eve held herself still as Roberta came on the strap-on, fucking it hard. It sent her over the top and she lost control as she fucked Roberta through both their orgasms. She fell on top of Roberta. They cuddled and hugged each other.

Later Eve slowly removed the strap-on and made sure Roberta hadn't been hurt. She kissed her and made her way down her body, slowly licking all her love juice up. She laughed when she saw how much had reached the suspender belt. They cuddled again when she had finished.

Finally, Eve said, "I think we need to shower. How can men wear this gel stuff? Bob you looked so hot. I hope my fantasy didn't go beyond what you were comfortable with. I love you."

Bob spoke quietly, "I never expected this. It was all you envisaged. Once I started and relaxed it just seemed so natural. I suspected you may want to use my bum as your instructions said to prepare myself. I was so unsure. I like playing in your bum so I said to myself I would give it a chance, fairs fair. I couldn't believe I would orgasm. The whole thing was great because it was with you.

"We've gone beyond the boundaries we had so often but I guess this was what this love month was about. By experiencing more things our love life is so much better. Our sessions with Sharon showed us how to listen to each other. We still have much to learn but everything we have done has been done with love for the other. That will never change."

Once showered, they retired to bed, husband and wife.

Day 29 -Wednesday - Revelation 4 - Jessie

Ted was wondering if he could manage to restrain himself from cumming so quickly tonight. From the others he had learned they were talking about events from the love months. Jessie and he hadn't reached there. He was so amazed at her descriptions of how she learned to do those roleplays. How many more did she have to tell him about. He couldn't ask her to miss bits as it was so amazing. Jessie even speaking about it was more then he could have ever imagined just four months ago. Sharon had been so helpful.

Over their dinner Jessie was teasing him. He was laughing which caused her to laugh. She couldn't be wearing a bra as her breasts were laughing themselves. His cock was wanting out, that was one of its favourite sights.

Once over, Jessie told him to shower and she'd meet him in their bedroom. It was prepared. When he entered it, Jessie was there wearing a lovely deep blue silk and lace nightgown which showed her of to perfection. She twirled so he saw the matching tanga panties hugging and caressing her bum.

Jessie playfully swatted his bum and told him to assume the position. He lay down in the middle of the bed. His cock was happy as Jessie slid over his body to restrain his arms and legs. He loved the feel of silk over him.