Alan Takes OverbyQuietoldie©
Helen and David submit to her workmate
My wife, and I are in our late 40s and we married in our early 20s and started a family straight away. The kids have now completed their college courses and live away from home. Both of us are followers rather than leaders and have not progressed very far career wise. I think Helen may be suffering a bit of "empty nest" syndrome as she has been very restless lately. She had low paid part time work before to give her more time and energy for our two children. More recently she applied for and got a new full time job. She is enjoying the challenge but needed to learn quickly and she has been bringing her work home to help get up to speed. Her mentor at work, Alan is clearly doing all he can to help this process. I am not really the jealous type but noticed she mentioned Alan's name quite a lot when telling me about her work. He is a few years older than us and it is obvious he has made a deep impression on Helen.
We had built up quite a lot of debt helping the kids through college so I encouraged Helen to see if it was possible to find a scam at her work to help pay off what we owed. This appeared very easy as security at the firm was rather lax. Easy that is until Alan caught her red handed. Helen came home one night looking ashamed and explained that she had pleaded with him to keep it a secret if she stopped immediately. He told her he would agree provided she agreed to do what he wanted. Helen told me she had agreed almost immediately. I realised from her demeanour that the prospect of submitting to Alan excited her. To my surprise I found the idea arousing too. He said she had behaved like a naughty girl and he would make her work late the following Wednesday night when she would receive a bare bottom spanking. He said he would film the spanking and give her a copy of the film to show to me.
"He was always ordering me around in the office, getting me to do menial jobs like make the coffee", Helen said blushing. "I enjoyed it—it was a sexual thrill"
"I noticed him looking at my legs and cleavage" she said. "I began to wear lower cut tops and shorter skirts to give him more to see". "Are you angry with me David?"
Perhaps I should have been but for answer I took her in my arms and kissed her hard on the lips. We exchanged tongues and began to frantically strip our clothes off. I bent her over the arm of the sofa and plunged my hard cock up to the hilt in her wet and willing cunt. Helen is usually quiet when we fuck but this time she was the opposite squealing and moaning with gusto telling me to fuck her harder. We both agreed it had been our best fuck ever.
I was beginning to believe we might have got away with our stupid attempt at theft but feared Alan could still change his mind. I suggested Helen go out and buy a few more revealing tops and even shorter skirts and allow him glimpses up her skirt and down her cleavage. Helen was all in favour. We fucked every night over the next week and Helen told me she was masturbating in the toilets at work thinking about Wednesday night.
On the morning of the spanking Helen said as we kissed goodbye,
"Will you be mad if he fucks me tonight?"
"Do you want him to?" (knowing full well what her answer would be)
"Well—yes I do. I've never felt so turned on by anyone in the whole of my life".
I wasn't sure if I'd wanted such a full answer and Helen said she was sorry after noticing the look on my face.
Yes, it was humiliating to hear but I found my cock stiffening.
I told her I was looking forward to seeing the film of her first venture into adultery.
On Wednesday, Alan cornered her at the lunch break to privately ask her about their assignation.
As usual he was forceful with his questions. She blushed with shame but explained she had been masturbating about it. She said she and David had greatly increased their love making.
"I may decide to impose limits on that kind of thing. Please use the Anglo-Saxon words in future. Now-- what were you and David doing?
.....Quickly, answer me, slut"
"We-We were fucking sir"
"Good. Well I hope tonight comes up to expectations. I hope you realise you've been flashing your yellow panties at me for most of the morning."
"Yes sir" she answered guiltily.
"Take them off—I expect they're soaking aren't they?"
Helen removed her panties. "Yes sir".
"You can sit at your desk without them all afternoon. And I don't want any other members of staff catching sight of your hairy cunt. Next time I want it freshly shaved."
"David can help you with that can't he?"
Helen smiled. "Yes sir, thank you sir." She informed me later she was pleased that there would be a next time.
That evening he waited until all the other staff had gone then, after switching on the video camera he made her bend over his knee. He took his time pulling her skirt back over her back slowly and deliberately. Helen said she was trembling all over. She has a big bottom but it is in nice proportion to her large breasts.
"This is what happens to naughty girls."
He began to slowly and systematically slap her bottom making sure he spread the slaps over all the areas of both cheeks until they became red (I could see this plainly on film later).
Helen had not been spanked for some years but the pain and the warm feeling was having it's usual effect. She was very close to orgasm.
"Have you had enough?"
Her reply was inaudible.
"Speak up, slut."
"More please, harder, sir" She whispered. "Then finger my cunt"
She could detect his erection through his jeans and pretty soon she was enjoying a noisy and physically out of control orgasm as he plunged two fingers into her.
He pushed her off his knee and, standing, removed his jeans and underpants in one swift movement.
She stared in awe at his beautiful cock.
"You and David want me to fuck you don't you"
"Yes please sir. We both do."
He pointed to his cock and she crawled over and began to suck it as he stood there. He grabbed her head and began moving into her, fucking her mouth.
"That's it, take it like the slut you are. I want you to swallow it all down."
He erupted at this point and Helen gulped on the jets of semen squirting from his balls, her hands round his upper thighs holding him to her.
His aim was maximum humiliation as he ordered her to strip and beg him "To fuck his slut's cunt" (he made her say the words). He bent her over the desk whilst he lewdly mauled her breasts plunging his cock up to the hilt without further preamble. He drove into her for what seemed like an hour as she coasted from orgasm to orgasm pleading with him to fuck her harder. She told me afterwards that she had loved every minute of it.
After she had received a further injection of semen, this time into her cunt, he told her he had plans for both of us and would visit our home in two weeks time.
We had to obey him or he would tell Helen's boss about the theft. The company had a policy that the police were informed automatically in this situation.
Helen and I talked it through and we agreed to submit to him. He knows I encouraged Helen over the theft and will administer my spanking when he visits. He wants me to dress as a woman and suck his cock. Helen is really excited by this prospect and has been out buying me some pretty outfits. She already has me wearing her pink lacy panties under my clothes and I love it. We like the idea of a strong man in our lives. I will admit that I liked the look of his cock. I have mixed feelings about taking it in my mouth but think about it constantly. Fucking her before his visit is forbidden so we have been watching the video together whilst she tells me how much she loves Alan's bigger cock. This makes me spurt into a tissue whilst Helen looks on with a broad grin on her face. I have not been allowed to watch her masturbating (Alan's rules). She has been doing it whilst I am out walking the dog and whilst she watches the film on her own. She likes to press the pause button at interesting places. At work she is very submissive around Alan and continues to wear slutty clothes. He appears unmoved and orders her around as before.
Fourteen days after Helen first cuckolded me I answered the door to Alan in a pretty French maid's outfit. I have always worn my hair long and Helen had lent me her rollers and put my makeup on. Alan seemed to approve.
"Fetch me a gin and tonic and make it quick- maid"
"Yes sir, certainly sir." I obeyed him as fast as I could.
I was thinking about what was to come and my bottom had that strange "curling up" feeling.
He ordered Helen to strip naked and closely inspected her shaven pubic mound.
"Ah! good. Now for the maid's spanking."
He made me bend over the back of one of our sturdy dining room chairs. My face was against the seat and he got Helen to tie my wrists to the front chair legs and my ankles to the back chair legs.
"She's been a very naughty girl hasn't she Helen."
"Do you know what happens to naughty girls?"
"Yes sir, they deserve a good spanking sir."
"Pull down her knickers for me"
Helen hastily withdrew my skirt across my back and brought the pretty pink frilly panties down as far as my knees.
"I see she's been freshly shaved as well" Alan said.
"Yes sir, we shaved each other" Helen said.
Before the onslaught started I found I was highly aroused, the bondage and humiliating position, my naked bottom sticking up in the air, my sissy clothing all helped. This was something I had been dreading and yet kind of looking forward to. Alan was using the flat of his hand but able to take long backswings. He was relentless, covering every area of my rear. The pain was excruciating but I was trying not to cry out. He said if I did I would get more. I couldn't help making low moans. My erection had subsided at first but then I saw Helen lying on the floor below me, her legs lewdly splayed out wide fingering herself. She was turned on by my punishment. The spanking was heating my bottom and the heat spreading to my loins. My cock was as hard as ever again. Had I been able to touch it, it would have exploded with cum.
"I fear your slut of a husband is enjoying this too much. I'll give her 20 more and then stop." Alan said.
"Yes sir, thank you sir" I said answering for Helen who was orgasming loudly below me.
Finally I was untied and told to stand in the corner and watch a real man at work.
They sat on the couch and began kissing. He was still fully dressed. The contrast with her nakedness emphasised his control. I could see them exchanging tongues. A hand stroked her breasts whilst his other moved towards her cunt. Helen's arms were around him. They kissed some more as she writhed on his fingers.
"Follow us upstairs maid. I want to fuck her on the marriage bed."
Once there he made me undress him and draw back the duvet. I could not take my eyes off his cock and noticed Helen staring too. He was like a rampant bull. He placed her in a semi-kneeling position in the middle of the bed with two pillows under her waist.
"Are you ready for another fucking?"
"Yes sir, I can't wait to feel you inside me again. Please fuck me with your big cock."
"Maid, be a good girl and take it in your hand and position it against the mouth of her cunt. That's right, perfect."
I had to admire his technique. He appeared to enjoy taking her from behind but they tried various positions before he spurted his seed well up inside my wife's vagina. Her excitement made her quite noisy and she had orgasmed frequently. Watching them excited me too and I spurted into my frilly panties, hoping Alan had not noticed.
He stood up and I saw that his penis had softened. He beckoned me over to him.
"Can you help me with this? I expect you've sucked plenty of cocks in your time."
"No sir, I never have- but I'll give it a try."
I knelt before him and took it in my hand. I kissed it lovingly, then took it in my mouth. I could taste and smell his sperm and Helen's juices. It was not unpleasant. I sucked on it using my tongue. I could feel it hardening and began to relax into it.
"Hmm. Not bad for a virgin cocksucker. I'll make sure you get plenty of practice over the next few weeks"
"Would you like to taste a few more cocks?"
This took me by surprise and I hesitated but Helen answered for me.
"That's up to you sir. But I like to see him giving head. He'll suck pussy too if you ask him."
"And I'll do anything you say from now on." She added colouring.
"Will you now?" Alan said "Well let's get you back downstairs and tied over one of those dining chairs. I'd like to try out that virgin arse of yours."
Helen submitted to this indignity willingly. She told me afterwards that she enjoyed the different feeling it provided. In some ways similar to the spanking but as her anus became used to the intrusion and the pain subsided she got a wonderful feeling across her vaginal area and by stroking her cunt in time to his thrusts had yet another orgasm which was unlike her others that night.
Our next meeting with Alan was at an hotel. He is a Major in the Territorial Army and said he wanted to reward his troops after a difficult exercise which had involved a week under canvass.
" They've not seen their wives or had a wank for at least a week so they will be horny as hell "
" And by the way one of them is female, but she'll be wanting to fuck you Helen, not David. I expect you've shagged a woman before haven't you? "
Helen blushed. " Not properly. I had a bit of a thing with a girl at school. It lasted for a year. She used to spank my bum and make me lick her out. Then she found a boyfriend and she lost interest. "
" Well. Well. By the look on his face, David had no idea. Am I right? "
I nodded, making a mental note to question Helen about it later. I wondered what else she had done that I didn't know about.
" Be there at 10pm on the dot. David may wear one of his pretty outfits but I don't expect it will stay on for long "
Now that Helen had realised I was turned on by her sexual behaviour she wasted no time in telling me about her affair at school. The girl was the most popular in her year (she was a year above Helen). She was very attractive and was captain of the hockey team. Although the girl was a bully Helen became besotted with her. She followed her around despite being ridiculed and humiliated by her and her friends. After hockey the girl told her to wait behind and gave her a good spanking in the shower. They were both turned on by the spanking and Helen knelt in front of her and licked her to orgasm. After that they would meet outside school at least twice a week.
" She treated me like dirt but we both knew it was a game. I was very upset when it ended "
" Have you done anything else sexual over the years that I don't know about darling? " I asked, partly dreading another revelation but partly hoping for another sexy story.
" Well, the answer is Yes, but I'll keep you guessing at the moment. You can ask me the next time you want a wank. I wonder how many times I'll get fucked this weekend and how big the soldier's cocks will be. Don't be shy- show me that little sausage you've got. "
I was still not allowed to fuck Helen but she watched me as I pulled down my frilly pink panties and began tugging on my penis. It didn't take long for me to spurt.
When we arrived at the hotel Alan was there on his own. The group had been treated to a slap up meal and were due in a few minutes. Alan had had a special door fitted to a walk in wardrobe with a hole about shoulder height. It was big enough to get a hand and arm inside. Helen was instructed to strip off all her clothes and stand by the hole in the dark.
" They will all get a chance for a feel. Please do not move out of their way. " Helen was happy to comply.
This was a totally new experience for Helen. Time was limited to three minutes and no speaking was allowed. She counted about seven persons and assumed one of them was the lesbian-the one with the long finger nails? Two or three of them became so fascinated with her breasts that they ran out of time before reaching for her cunt. They were all careful not to be too rough. One reached down to her cunt straight away and began finger fucking her bringing her to a noisy orgasm. The others in the queue cheered. Helen was loving it and it got the evening off to a good start.
The men and the woman were all in their dress uniform looking very smart. As they entered the main room after feeling up Helen Alan introduced me to them as Helen's husband and I said;
" I am a panty wearing sissy who likes to watch real men fuck my wife. I am at your service for the night and hope you all have a lovely evening. "
I could see the bulges in their trousers and knew what had been the cause.
They all grinned or laughed out loud at my speech. Some kissed me on both cheeks or on the lips and I got a very nice hug from a couple of the men. The woman formally shook my hand but there was a twinkle in her eye.
They were ushered to a table in the middle of the room and they all sat down. The table had a heavy table cloth which hung down on all sides reaching beyond their knees.
As instructed Helen now came out wearing a barmaid's outfit to take orders for drinks. Her dress was so short on top that her nipples were on show. Her skirt was hardly long enough to cover her bottom and she did not have any panties on. Alan demonstrated to the others that she was happy to be touched. In fact she thanked anyone who tried and did not move away.
Alan signalled me to come over and remove my pink dress. He was at the head of the table and stood up so that I could crawl on all fours under the table in my underwear.
" David wants you all to fuck his wife tonight and to get you in the mood he will move amongst you and try to get you excited. Can all the men unzip your trousers and release your dicks but keep them hidden by the tablecloth." The woman, not wanting to be left out, stood up at this and quickly removed her knickers.
Alan nodded his approval.
"Let the game commence. We will all closely observe what is going on based on facial expressions. Try not to let on that he is paying attention to you when it happens."
All the group moved forward in their seats and they all sat open legged in readiness. It was a bit dark under there but I could see Helen's legs as she moved around the table and heard muffled moans as she opened her legs and allowed herself to be finger fucked by anyone who wanted to. I took hold of my first cock and moved my mouth towards it. To my surprise the cock shot a load of cum into my mouth before I had time to suck it. I swallowed it down and moved onto the next man. This happened two or three times as the young squaddies found it difficult to avoid ejaculation in such a sexually charged atmosphere. I came to two bare legs and began to lick on the woman's pussy. She was soaking wet and appeared to welcome my tongue. I moved on. Most of the cocks were bigger than mine. They were all chatting and laughing above me and the pretence of indifference made it especially humiliating for me. One man was particularly well endowed so I took a long time with him enjoying the feelings of inferiority towards such a superior specimen of manhood. Under cover of the tablecloth I pulled on my penis as I sucked his cock.
I came out from under the table to a round of applause and choruses of "Cocksucker. You're a cocksucker."
Helen told me later that three of the soldiers had blushed with embarrassment at accepting a man's mouth on their cocks, thus giving the game away. Three men were undetected and the woman.
"These four can fuck Helen before the rest." Alan said. " I think we'll let Bridget go first."