The Guilt Trip

This story is a total fantasy. There is no under age sex or cruelty involved. I hope you like it.

*****

It was Tuesday morning. John Goode woke suddenly and heard his wife Jennifer downstairs cooking breakfast. He walked over to the window and peeped out. It was a beautiful day. He smiled as he saw a young squirrel shooting across the back lawn with a nut or something clutched in his claws.

He slipped into the shower and in a few minutes was out and dressed ready for the day to come. John padded downstairs just as Jenny was sorting his toast out and smiling "OK Love? It's a lovely day."

He kissed her on the side of her cheek "It certainly is Love, have you heard anything from the twins?"

She nodded "Yes, they have arrived safely with the rest of them in Bournemouth and are quite happy with the hotel facilities and looking forward to the scouts rally later on today. They are looking forward to everything that will happen this week. They really are remarkably confident for their age."

John smiled. Jennifer was quite right. The twins Billy and Brian were only 11 years old but were really self sufficient. Whenever he expressed this thought, his wife would always come back with "Just like their lovely father."

After breakfast he put on his tie and suit coat as he sorted his briefcase out. He had a few important meetings before noon and then he was relatively free. He always discussed his work with Jenny and she asked "I hope Molly will have everything ready for you. How is she now?"

John knew what she meant. Molly Bell, his secretary, was in her very early fifties and had lost her husband Bruce, 6 months earlier in a car crash and had been devastated. The two couples had been close friends for many years. Jenny and Molly would go shopping together at least once a week whilst John and Bruce really enjoyed playing darts in the local pub every Wednesday.

He said " It was hard for her during the first few months, but we all looked after her and she really appreciated your support. She's coping quite well now and I know she'll have all the papers ready for me when I need them."

Jenny nodded "She always reminds me of Mrs Kelly. She seems to manage any number of tasks without getting flustered and still finds the time to clean the church and sort out the flowers for the altar.

John murmured "Yes, she's a remarkable woman."

Jennifer continued "Not only Mrs Kelly, John. It is much the same with Mrs Shaw the Church Housekeeper. She's only supposed to look after the house but she is always helping Mrs Kelly sort the church out."

Her husband nodded "I suppose they really try to make it as easy as possible for Father Francis. He is a great priest but he's getting on a bit. I'm not sure that the next priest will be as good as him. We all have to help him."

Jennifer looked concerned "Well, you can't do any more John. You already look after all the Parish finances and assist Father Francis say Mass. You are a sort of unofficial curate. You have enough to do."

John smiled and looked at his loving wife. Sometimes he felt she was a bit over protective.

Jenny added "I think it is about time we invited Molly over for an evening John, we all enjoyed each other's company when Bruce was alive. I like to think we are all good friends."

John nodded. His wife was right. He was always amazed how his secretary managed to keep their friendship so separate from their business relationship. In the office she always referred to him as Mr Goode and never ever commented on anything personal. She really was the ideal secretary. He was even thinking of promoting her to his Personal Assistant but decided to wait a few months.

With these thoughts in his mind, he kissed his wife on the forehead and left to get in his car. He called back "I will probably be a bit late tonight, I have a few things to do before I get home."

When he arrived at work, Mrs Bell had already stacked up his business papers at the front of his desk. As he sat down she came bustling in with a steaming cup of coffee saying "Everything is ready for you Mr Goode but before you do anything, drink this coffee. We have to look after you."

John wanted to laugh. She acted like his mother. He knew she didn't want any sympathy these days. He looked at her gently "I don't know what I would without you Molly. You are a gem." Actually she looked so nice and plump, he did have some secret thoughts but he had too much respect for her to let them slip out.

She looked at him hesitantly before saying "I hope you don't mind, Mr Goode, but I have some important business to carry out this afternoon. Would it be acceptable to you if I left early. I will make up the time later in the week."

John laughed "Of course I don't mind, Molly. And don't worry about making up lost time. You do enough when you are here."

Mrs Bell blushed "Thank you Mr Goode." It always amazed John how is secretary would always refer to him as Mr Goode in the office. He would frequently tell her his name was John. She would have none of it. In the office he was Mr Goode, whilst in their personal life he was John. She would relent in one small way, in that, when he took her for occasional office lunches she would refer to him as John. It was a bit complicated.

John had a very satisfactory morning and saw the three important clients. As she wheeled them in at the appropriate times, Molly also brought some more coffee. This time she also added some nice custard cream biscuits which she knew were John's favourites.

When the last visitor had left, he sighed with relief and started to think about the secret events that the afternoon would bring. He was a little ashamed of his thoughts but the pressure had been building up over the last 5 or 6 days. He knew it was inevitable.

He told Mrs Bell he would also be leaving early. She simply nodded. She would never dream of asking for reasons. He was in charge.

Towards the end of the morning, John's thoughts were elsewhere. He felt guilty but he couldn't help it. As he left work he walked to the Executive Car Park where his distinctive limo was. He looked around. He could see no one so he opened the door and sat in the drivers seat. He waited there for five minutes and looked around. No one was watching.

He drove to the exit. He normally turned left to head for home which was only a short distance away. Today he turned right, feeling reassured that no one was watching.

After going through several villages he pulled into a small car park adjoining a rather seedy looking hotel. He gathered up a medium size bag of clothes from the boot and headed towards the front door.

Inside he saw the male receptionist wearing a grubby blue shirt. John wasn't surprised, he had seen him before. He simply said "I want to use Room 15 for one hour." and pushed £20 across the counter.

The man nodded and stuffed the money into his pocket. No books were signed. John took his bag and walked down the corridor to Room 15. He knew it well.

In Room 15 John emptied the bag onto the bed and changed. He packed his own clothes into the bag and walked back up the corridor, past the man without saying anything and out through the door and into his car.

He felt safe now to enjoy himself. He left the car door open for a few minutes and luxuriated in the feeling of his high heels on the tarmac floor and the black stockings and his patterned dress. He felt so excited he couldn't stop smiling knowing that he felt so attractive with his blond hairpiece and red lips.

He sat there for 5 minutes enjoying himself and to make sure no one was watching and then drove off. It was a fairly long drive until he came to a very affluent area and carefully drove down a long cul de sac with a lovely avenue of leafy trees. This was an rich district. You could almost smell the money.

Right at the end there was a lovely detached villa with quite a long driveway. He carefully entered the driveway and parked as near to the front porch as possible.

A tree from the garden had overhanging branches which sheltered the car from the warm sunlight and from any prying eyes.

John sighed heavily. He was excited. It was always like this. A long build up of tension and excitement. It was incredible. He knew it would get even more intense.

Before he would be allowed to enter he had to make a telephone call. This made him nervous. He wanted to delay.

It was still so quiet. He opened the door and pushed his high heels out onto the driveway. The luxury of it all took over again. He leaned back fully into the car so that his silk dress tightened into his lower area. He was getting bigger.

He gasped. It was so silky and shiny and satiny. He felt himself growing even more down there and he pressed himself. It sprung up so easily. Amazing.

He had to make the phone call on his mobile. It rang for so long, he thought she may be out. And then "Yes, who is it?"

He panted "Its John, Mrs Smith."

"John?"

"Yes John Goode. I hoped you could see me."

"I see. Do you really want to see me, John?"

"Yes please Mrs Smith. I have been thinking about you for several days now."

"You sound desperate John."

He felt so guilty. "I am Miss. I have dressed for you."

There was silence for over a minute. John was holding his breath. Surely she would agree to see him.

Then she broke the silence. "I assume you are pretty, John."

He was bursting to tell her "Yes, Miss. My shiny shoes and black silk stockings and nice silk dress."

She was speaking slower now and very relaxed but probing "But there must be more than that John?"

He panted now. He would tell her everything "Yes Miss, panties and bra and my suspenders."

She chuckled "You like your suspenders, don't you John. Makes you feel more girly?"

He felt ashamed and guilty at those words but he panted "Yes Miss."

"Do they excite you Joan?"

He blushed at the feminine name but felt very aroused "Yes Miss."

"And your brassiere. What colour, John?" She had reverted to his proper name. He felt so mixed up.

"Pink, Miss."

"Do they cover your Tits, John?"

He felt embarrassed. "Yes Miss."

"Tell me about your panties, John."

He was really excited now "They are lovely silk ones Miss. White silk panties." Even the words excited him.

"Where did you get them?"

Now he felt his face go red and he was so guilty. He mumbled something.

"Pardon John?" He mumbled again.

He heard her laugh and then "So you are wearing your wife's knickers, John? Jennifer's knickers?"

He wished she would stop teasing and open the door for him, but he had to answer "Yes Mrs Smith."

"John, wait a few minutes. I will unlock the front door. Open it and go into the hall and then upstairs. Go into the second bedroom on the left and lie on the bed. You can slip your panties off and play with it if you wish."

He gasped. At last. He waited the few minutes and then carefully opened the door and went into the house. Up the stairs and there was the bed.

He couldn't help himself. He slipped his wife's underwear off and started to touch himself under his silk dress.

It was such a wonderful feeling that he half closed his eyes.

Then a low husky voice murmured "My, my, what a pretty boy we are today Joanie. Beautiful dress, and stockings but no panties."

John felt so embarrassed at the words Mrs Smith was using, but he was even more intimidated by her manner of dress

She was standing at his bedside looking down at him in all his frillies, but she also had her skirt right up to display a large strap on penis. It was jet black and made his eyes water.

She murmured "Hold it Joan. You may as well get to know it now as you will be very familiar with it shortly. John raised his hand to grasp Mrs Smith's black penis.

It was a very erotic scene as his own penis was a vertical pillar. He felt lost, guilty, and ashamed but incredibly excited as he made a fist around her projection. He felt feminine.

"Do yo like it John. Is this what you have been thinking about all morning when you were with your wife and then later in your nice office with your lovely plump secretary?"

He felt helpless as he confessed "Yes Miss."

Even as he spoke she was crawling onto the bed with his head between her legs in a straddling fashion as she reached down and let her tongue circle the head of his penis.

He almost sobbed "Oh God!"

She was an expert. She wriggled over his face, first of all rubbing her vagina over his face and then moving down even lower so that she was more comfortably astride.

Her bottom cheeks were pushing into his face. Over his mouth. She knew his secret thoughts.

She murmured loudly "Nice strong buttocks John. You like my big buttocks don't you."

He mumbled his excitement. She wriggled again and she ordered him "Push your tongue out John, lick it."

He had waited for this so long. His guilt was forgotten as his tongue poked out.

She was enjoying it and teased "That's right John, lick it. I want you to lick my big strong arse."

He half sobbed as he followed her commands and her mouth enveloped his penis bringing him nearer and nearer to fruition, but not too near. She had more plans for this happily married man. She took him to the brink and then released him saying "We have a lot more to do today John. I need satisfaction as well as you."

John whimpered as she said "It will be time for Big Sam to have his pleasure shortly John."

He knew this would happen. It always did. He thought he would be tested first. He was right.

Mrs Smith told him "Turn over on the bed John, partly on your knees. We have to test you out with Mr Bluey first."

He did as instructed and felt her insert something between his buttocks.

He knew from experience that it was her favourite butt dildo. It was quite large and sky blue.

As, on previous times she pushed it up slowly and then slid it up and down a few times. Each time as it went up he couldn't suppress a huge sigh of satisfaction.

She whispered "I think you are ready now Joanie."

He whimpered "I am ready, Mrs Smith."

"Ready for what, Joanie?"

She was now using the more familiar girly name.

All shame and guilt were gone now "Ready to be fucked Mrs Smith."

She helped him up from the bed and led him over to the black easy chair in the corner of the room.

He knew the drill. He knelt up on the chair, silk dressed pulled up at the back and his bottom exposed.

She climbed up behind him and eased herself into his bum. He was being mounted.

As she thrust he gurgled with pleasure. She asked him, who do you think it is, Joanie?"

He panted "Is it Big Sam, Miss?"

She thrust up him again and giggled "You like Big Sam, don't you Joanie?"

She gave another little thrust as he gasped "I love Big Sam Miss."

For the next half hour Mrs Smith and Sam took John Goode to heaven. It was so wonderful and it seemed to get better each time he had this secret adventure.

Finally he was spent and simply flopped over the back of the chair as Mrs Smith stood back waiting for him to recover. She handed him the bag of clothes "You change back in the upstairs bathroom John. I will go to the downstairs bathroom. When you have finished come downstairs. Do you want a cup of tea?" She seemed so much more gentle now.

He looked subdued as he murmured "Yes please Mrs Smith."

Half an hour later he slowly made his way downstairs.

His wife had laid the table and was pouring a cup of tea for him. She smiled and handed the tea to him saying "Do you feel better now John. Did you enjoy it."

He looked at her gratefully "Thank you so much Jen, it was wonderful. Was it alright for you?"

Jennifer laughed "It was great John. I have been looking forward to it for the last three days. Its lovely when the twins are away."

He nodded "I thought about it all morning Jen. I felt a bit guilty. It was a good job that Mrs Bell had all my papers in such meticulous order, I couldn't go wrong."

Jennifer looked at her husband lovingly "First of all John, you have no reason to feel guilty. You are a good man and a loving husband and father. I know you love me."

John felt relieved "Thanks Jen. I suppose I need reassurance."

Jennifer laughed "I love you very much but you should know something else."

"Tell me Jen?"

She laughed again "Mrs Smith enjoys your visits very much John and so does Big Sam."

They were both giggling now and carried on discussing Mrs Bell."

Jennifer commented "She is a good secretary for you John. And a good friend to me, when we were in school together and later on. She was like an older sister and taught me a lot of things. You should make her your P. A."

John smiled "You must be a mind reader Jen. I have been thinking of doing just that for a while."

They were both so relaxed now as they settled down with a few biscuits.

Jennifer reverted to talking about Molly Bell. "You know she adores you John."

John smiled "She is gorgeous, Jen, but I cant really take advantage of her."

Jennifer spoke seriously "Why not? She is nice and plump and you always said you liked older women with some meat on them." She added with a giggle "And she is motherly which I know you like."

There was a photograph of Molly on the sideboard and Jennifer seemed determined to tease her husband. She picked up the picture and flashed it before her husband's eyes "Just look at her John. Be honest, you must fancy her. She's the ideal plump mother figure for you."

He looked at the image and growled "Don't keep on Jen or I'll tell you what I would like to do to her."

Jennifer was still feeling aroused after her Mrs Smith performance and pushed him further. "Go on John, tell me what you'd like to do to her."

John cracked "God, I could fuck her. I would really like to fuck her."

Realising what he had said, he started to apologise. Jennifer didn't want any apologies "Don't say sorry, John. It is exciting. I would like to watch you."

John was breathing heavily. "Watch me? How do you mean Jen, watch me?"

Jennifer was excited but much more in control than her husband "I'd like to see you fuck her, John. It would be exciting for me."

It was all becoming much more real now for both of them "It would be exciting Jen, as long as you don't mind."

She shook her head "No, John. I wouldn't mind. In fact, I'd like to do it as well."

John looked puzzled again "How do you mean Jen. Do it as well?"

Jen breathed heavily. She didn't hold back "I'd like to fuck her as well. As I said she was like an older sister to me and we did some juicy things together but it stopped when she married Bruce. She was devoted to him."

John looked dazed. They were talking about his dead friend's wife. She was also his secretary. She was so motherly. He should have felt guilty, but he didn't.

One of his fantasies was to watch to see what lesbians did to each other. Jennifer knew, and egged him on "I could fuck her in front of you John. You'd like that, wouldn't you."

"God, yes. I really would like it."

Then reality struck "But it wouldn't be possible. She wouldn't agree."

His wife was way ahead of him. She had clearly put a lot of thought into it.

"Of course she would agree, John. You know she adores you and Bruce was never up to it."

John knew what she meant. His friend was a small man and his manhood was tiny. It had embarrassed him. On occasions after a few pints Bruce had told him that he felt he wasn't worthy of his wife. She had always been a very 'full of life' person and he was letting her down.

John had always been sympathetic but his guilty thoughts always returned later on thinking and wishing that he could help his friend out.

He had discussed the situation at various times with Jennifer she told him that Molly had confided the same things to her and it was all very sad. Jennifer had hinted several times that it had been an exciting period for her before Molly had met Bruce.