"Backhander" by Lucy Roberts. If you like this story please let me know
Ian was busy at his desk. It had been quite a heavy Friday and now, mid afternoon there was still a bit to be done before the weekend but there was also the promise of the evening at home and weekend alone and all that that might mean.
He ran his hand down the front of his jumper and felt the slight swell. Today he had come to work wearing a bra as well as the panties he usually wore and he had added just a hint of padding in the bra. He felt good as his hand ran over the slight mound. His prick twitched in his panties.
"Day dreaming again Ian?" said a voice just behind him? It was Rob.
Rob was in his late 50's and had worked in Social Services for ages and often worked on cases with Ian. But, like everyone else, was totally unaware of Ian's other side and Ian wanted it kept that way.
Rob had come over to discuss a case and watched over Ian's shoulder as he brought up the file on the computer. They looked at it together and then as they parted Rob rested his hand on Ian's back, right on top of the catch on his bra. Ian froze but Rob said nothing and went back to his desk.
Ian sat there almost unable to move with panic. But Rob had said nothing and as the minutes passed by nothing was said. After about 15 minutes Ian decided to go to the toilet. He went into a stall and pulled his trousers and panties down. He sat there looking at his panties, they were black with a lace front edged in red and very sexy. The feel as he pulled them back up and tucked his penis under him to create a female front reassured him that, whatever the risk, he needed to wear these things. With a bit more confidence he stepped out of the stall to be met by Rob.
"Oh hi Rob," Ian spluttered, his confidence draining away.
"Hi," Rob replied. "Ian I think you have a little secret. Would you like to share it with me?"
"I don't know what you mean."
"Yes you do," said Rob. "You went white when I put my hand on your back and found something there that most men don't have. You are wearing a bra and I want to see it."
Ian gulped. What should he do?
"Don't worry, I haven't told anyone and don't intend to. Just lift your jumper and shirt and let me see."
Ian had no choice. He pulled his jumper and shirt up and let Rob see his bra. It was black and very lacy with just a little padding in. Rob reached out and touched it.
"Hmmm. Very nice Ian but your boobs are a bit small. Still you don't want people in the office noticing do you? I bet you're wearing panties as well aren't you?" Ian nodded.
"Well don't keep them to yourself drop your trousers."
Ian's stomach turned over. What if someone came in and saw and yet he could tell from the twitching of his penis that he was getting excited at this. He quickly undid his trousers and let them fall round his ankles and then pulled up his jumper and shirt again so Rob could see all his undies.
"Oh yes." said Rob. "Very sexy indeed." He ran his hands over Ian's bottom and then down the front of his panties.
"Very feminine Ian. I think we should talk about this. Meet me in the George after work."
With that he turned on his heel and left. Ian just stood there stunned with his trousers down and shirt up. He'd only just come back to earth and got rearranged when someone else came in. Ian hurried out and went back to his desk. But the chance of doing any work was small.
Two hours later found him and Rob sitting together in a corner of the local pub.
"Well this is a surprise. Who would have thought it of you Ian! But don't worry I'm not going to tell anyone. Does anyone else know about this?"
Ian said no.
"Well now I know. Has anyone every seen you dressed before?"
Again Ian said no.
"Look tell me all about it. I can be a very sympathetic listener and it might work out to your advantage."
Ian decided he had nothing to lose. He told Rob his story from the early days of wearing his mother's undies, through beginning to buy his own, to the luxury of having his own flat and being able to wear what he liked when he liked. Rob listened carefully. So carefully that he recognised what Ian had missed out.
"But how do you feel about this? How do you feel when you are dressed as a woman?" Rob asked.
"When I'm fully dressed as Lucy," this was the first time that Ian had let his femme name out, "I feel and act like a woman. For instance if I'm watching a film I identify with the woman."
Rob pounced on that remark. "So if the woman is being kissed," he said, "you identify with her?"
"Well yes I do," said Ian blushing.
"But no one has ever seen you dressed and so no one has ever kissed Lucy," Rob asked.
Ian shook his head.
"But would Lucy like that," Rob continued.
"I don't know," said Ian.
"Look," said Rob, "I've a suggestion. You don't have to agree and if you don't this won't go any further. There is no blackmail on offer here. But why don't you go home and get dressed and then in a couple of hours I'll come round and meet Lucy and we'll see how it goes from there?"
Ian didn't know what to think. He had set off this morning as normal with his secret very much a secret and now everything was on its head and that thought, which had been deep in his unexpressed feelings, of being with a man as Lucy was being offered to him. But did he want it and why was Rob doing this?
"But Rob," Ian said, "I'm a man."
"Yes I know and I'm bi-sexual and I have been with TV's before so don't worry. I know what I want but do you?" Ian wasn't sure but he couldn't think of a better or safer opportunity to find out.
"O.K." he said, "give me a couple of hours to get home and become Lucy and then come round."
Ian almost sprinted out of the pub to his car. On the way home his mind was racing with what to wear. He mentally went through his various outfits. All the time excitement was building but also a little fear of what might happen.
Once at home he stripped off, lingering for a moment over his bra and panties and trying to recall how it had felt when Rob had touched him. Ian stepped into the shower and washed and shaved off what little hair he had on his body.
Once he was dry he went into his bedroom. He took out a white suspender belt and clipped it round his waist. He opened a new packet of black stockings and sat on the bed and drew the stockings up his legs. They felt sooooo good against the freshly shaved skin! He stood up and took a pair of white panties with lace panels in the front and a lace bow , so pretty and so feminine. Just putting them on and tucking his penis out of the way made Ian feel so girly. He went to another drawer and found his favourite white bra. It was under wired and its tightness caused the flesh on his chest to be drawn together in the illusion of breasts so that he only needed slight enhancers to fill out the 'b' cups of his bra. He then put on his white slip. The feel of silk on silk over his bottom and legs was sensational.
He walked across to the dressing table and sat down. One of the joys of living alone was that he was able to leave his make up and things out so that his bedroom looked like a woman's. Now he went to work on his face with practiced skill. Never had he been out dressed but he liked to think that he could pass. Finally he was happy. He looked at his watch. Time had rushed on and Rob would be here in about fifteen minutes. Ian put on his wig and checked how he looked. Yes she was happy with how she looked. She sprayed herself with deodorant and went to the wardrobe. She had already decided on her black dress. It was quite plain, coming down to just above her knee with short sleeves, but it fitted her well and accentuated her feminine shape. She stepped into it, drew it up and zipped it up. Then she lifted the skirt and pulled her slip into place. She was almost ready. She stepped into her high heels. The last thing was to put on her jewelry, a ring on each hand, her watch and two bracelets, her ear rings and a nice gold necklace. Then just a dab of her favourite perfume on her wrists and neck and she was ready.
Or was she? As she looked at herself in her full length mirror she was happy with what she saw but inside her stomach was churning with the thought of someone else seeing her like this and that someone being a man who had already expressed sexual desires towards her!!
She went down stairs and got herself a gin and tonic. She sat down. What did she want? What would she let happen tonight? Kissing? Touching? Could she touch a man, touch his prick? Could she do more, kiss it suck it? Oh she knew what it was all about but was this what she wanted? Did she want him to make love to her? Her mind was a jumble.
She stopped and stood up and drew in several deep breaths.
"Get a grip," she said to herself. She walked over to the hall mirror.
"You are Lucy," she said to the reflection.
"You are a woman. In a moment a man is going to come in that door. It is no big deal. Be the woman you are and don't worry about what might or might not happen. Let it happen if you want or not if you don't. But don't miss this golden opportunity because of fear or panic."
Somewhat calmer she sat down again and began to relax. The doorbell went. Lucy stood up smoothed her dress down and went to the door.
Rob was dressed in an open neck shirt and casual trousers and a jacket. He came in and looked at Lucy.
"I am impressed," he said. "You could have walked passed me in the street and I wouldn't have recognized you. You look lovely."
"Well thank you kind sir," said Lucy. She led him into the lounge very conscious of two things. The first was that Rob's eyes were on her and the second was the sensual feel of her clothes and especially of the suspenders pulling on her stockings. She felt very much like a woman.
She sat Rob down and gave him a drink and returned to her own chair. They chatted for a while about the house and Lucy's life and interests. Lucy was aware that Rob's eyes were wandering over her and especially over her legs. She was careful to keep her skirt down and legs together as befitted a lady but she was also aware that she was enjoying the attention.
After a while Rob said, "have you ever been out dressed?"
Lucy said she hadn't.
"Well then," said Rob, "let's go."
To Lucy that was easier said than done and for a while she came up with plenty of reasons why she couldn't go out as she was. But gently Rob reassured her that all would be well and so it was that less than an hour after Rob had become the first person to see her as Lucy she was changing into flat heels, putting on her jacket, checking she had everything she needed in her handbag and stepping out of her front door for the first time as Lucy.
It was a warmish evening and quite dark, which helped Lucy. Rob took her hand in his which also helped. They headed towards the shopping area and talked easily as they went. Some people came towards them and Lucy's heart was in her mouth. Had she been on her own she might have turned and run or at least crossed the road but with Rob holding her hand she couldn't. But they passed and nothing happened and as others did the same Lucy began to relax and enjoy the experience.
She could hear the rustle of her clothes, her stockings against her slip and dress and the clack of her heels on the pavement. They came to the shops, where there were a few more people. They stopped outside one or two shops and Lucy rather than looking into the shop looked at her reflection in the window. She was beginning to enjoy this. One shop that she did look into as they stopped was the lingerie shop. Rob was full of ideas of what she might look good in and she gave him a playful punch and told him not to be so rude.
They wandered on and Rob suggested they go into a pub for a drink but Lucy felt that she had had enough time in public for one night and determined to go back to her house.
Back inside she slipped off her jacket and changed back into her high heel shoes. She was just getting them some more drinks when Rob came up behind her and put his arms round her. He kissed the side of her neck and he pulled her to him.
"You are one lovely girl Lucy," he said.
He turned her round and kissed her. Lucy opened her lips and allowed his tongue entry into her mouth. His skin was rough against hers. His tongue was firm and strong as she licked and sucked on it. His arms were round her and she could feel his prick against her tummy. Well here was the moment of truth. The moment when reality bit in. How did she feel? The answer was clear. She felt like a woman. The dressing, Rob's appreciation when he first arrived, the awareness of him watching her as he would any other woman, the walk and being seen as a woman, and now the arms of a man round her all totalled up to her feeling more like a woman than she ever had before and to really enjoying that feel.
She relaxed and let her hands go round Rob. He sensed her responding and allowed one hand to roam over her back and onto her bottom. He gently squeezed her cheeks as they continued kissing. Then he broke off and Lucy was surprised to find she was disappointed, but not for long. Rob led her to the settee and they sat together. He began to kiss her again. His hand went onto her leg and slowly began to go up under her skirt. Lucy had no intention of stopping him. Indeed she was enjoying it and happy for him to continue.
But Rob was treading carefully so he wasn't rushing it. They kissed and then he pulled away.
"O.K.?" he asked.
Lucy was breathless and simply murmured, "yes fine."
"Is it just like the films?" Rob asked.
"No," said Lucy, "this is much better!"
That was all the encouragement that Rob needed and he took Lucy in his arms to kiss her again. His hand this time reached up her skirt and found her stocking tops and began to gently touch the soft silky skin of her thigh. Lucy twisted a bit so he could reach her bottom. Lucy was having trouble containing herself. This was so good. Rob was gentle yet strong and he was making her feel so much a woman.
For a moment they stopped and Lucy looked down to see her dress rucked up and her stocking tops clearly on show.
"That is a lovely sight Lucy," Rob said following her eyes.
"You cheeky man," Lucy said. "a true gentleman would avert his eyes."
"Not a bit," Rod replied, " a true gentleman knows what a lady wants and how to treat a lady. I sense this lady wants to be appreciated as a lady and treated as the woman she is. Am I right?"
"I think you are," said Lucy.
"Then perhaps we should go to your bedroom," said Rob.
Lucy stood up and Rob knew he had read the signals right.
Lucy led the way upstairs with some difficulty as Rob had his hands up her skirt. She went into the bedroom and closed the door behind Rob.
"Well this is certainly a woman's bedroom," he said and took Lucy and kissed her.
There was no doubt that he was turned on from the hard bulge that pressed against Lucy. Rob took hold of the zip on her dress and slid it down. He edged the dress off her shoulders and kissed them gently and then eased the dress to the floor. Lucy stepped out of it as Rob stepped back to look at her.
"Oh so sexy and so desirable Lucy," he said.
He slowly unbuttoned his shirt and took it off. Then he undid his trousers and took them and his socks off. He stood there in just his pants.
"Come here Lucy," he said.
Again they kissed as Rob allowed his hands to feel the soft material of Lucy's slip and she in turn felt his strong back and chest.
"Now," he said. "I want you to take my pants off me."
When Lucy reached out to do it he said, "No kneel down and take them down."
Lucy knelt in front of him and grasped his pants. As she pulled them down his prick sprang out in Lucy's face as Rob knew it would. Lucy knew what Rob expected. She hesitated for a moment and then allowed her fingers with their red varnished nails to encompass his prick. It was hard and soft. She look up at him and with his eyes he encouraged her on.
She bent her head towards him and let the prick slide across her lipsticked lips and into her mouth. It didn't taste bad it didn't feel bad in fact to Lucy it felt fine, just right. She was a woman and she was sucking her man's prick. It was right. Her hand ran over her breasts down her front feeling her suspenders under her slip. Yes she was a woman, doing what women do and she felt wonderful and by the sounds that were coming from Rob he felt pretty good about it too.
Lucy allowed the prick as far into her mouth as she dared. She knew about deep throat but that was not in her scope. But she sucked and licked for all that she was worth and as Rob groaned it was clear she was worth quite a bit. She stood up and Rob led her over to the bed. They lay together arms and legs entwined as they kissed and touched each other.
"Lucy are you ready to make love," Rob asked after a time?
"Oh yes," said Lucy.
"Are you sure you want to?" he asked.
"I would be very disappointed if we didn't," was Lucy's reply.
Rob got her to kneel up on the bed and too the lube that Lucy gave him. He pushed up her slip onto her hips. Then for a moment did nothing.
"What are you doing?" she asked.
"Just looking at one of the most beautiful sights I'm ever likely to see," he said. "Your legs are so long and the stockings make them look so glamorous. Your hips and bottom have a lovely feminine shape and those panties are so sexy. You are so much more like a woman than most women I've seen."
Then he pulled her panties to one side.
"Oh yes," he said "and a shaven pussy to boot."
Lucy was pleased because she had taken great care to shave round her vagina.
Rob began to lube her. It felt cold but very nice as his finger pushed inside her.
"Oh Lucy you are very tight. I'm afraid this is going to hurt you a bit but it will be nice and tight for me."
"Typical," she replied, "we women get all the pain and you men all
the pleasure."
And to start with she was right. Rob slowly located her rosebud opening with his prick and gently began to push until he was in. It hurt! He stayed still for a few moments and then began to push further in. It hurt even more. Lucy wondered if she did want this. If it was just pain then she didn't. But slowly as Rob eased his way further into her cunt the pain began to subside. Now Lucy could feel him inside her and he began to pull out and then slowly, gently push back in and the whole feel changed.
No longer did it hurt now she began to enjoy it. His prick filled her and then emptied her as it pulled back. Though she didn't realise it, each time Rob pushed a bit deeper inside her. His hands were on her hips helping him to pull her onto his prick.
After a few minutes he stopped. "That's it," he whispered into her ear, "you've got all of me in you. How does that feel."
"Oh indescribable. It feels wonderful. Now fuck me please."
So he began to pump in and out. The lube did its work as his prick slid in and out of her wet hole. Rob moaned with pleasure as Lucy almost shrieked with the joy of it and urged him to fuck her.
Rob came to a stop and pulled out and for a moment Lucy thought that was it but he simply turned her over and pulled her legs up onto his shoulders and slipped his prick back inside her waiting cunt. He leant down and kissed her rubbing her breasts as he continued to plough into her.
After a few moments Lucy's legs slipped off his shoulders and came down round his waist where she could grip him and hold him inside her. Now locked together they moved as one until with a gasp Rob came.
Lucy could feel his cum shooting up inside her. It was a most amazing moment.
For a while they lay there and Lucy could sense his prick shrinking inside her.
"I'm afraid there is going to be some mess," he said.
Lucy lay still for a moment and then reached out to her bedside table. First she gave Rob a tissue from the box on top of her table. Then she reached in the draw and found a sanitary towel.
She gave Rob the tissue and as he pulled out and wiped himself she stuck the towel inside her panties.
While Rob went into the bathroom she walked over to her dressing table to repair her make up. As she did so she could feel his cum dripping out of her vagina and into her towel. Oh yes she was a woman all right.
Once Rob was back in bed she took a spare pair of panties and went into the bathroom.
Sitting on the loo she got rid of all Rob's seed. What a pity she couldn't become pregnant!
Then she cleaned herself up and put on her clean panties. She put the soiled ones to one side. Perhaps she would wash them or perhaps keep them as they were, a reminder of he night she lost her virginity.
She went back to join Rob in bed.
"How do you feel?" he asked.
"It is so hard to describe," Lucy said. "I feel so amazing. I feel so much like a woman. I feel I just want to run outside and tell everyone that I'm a woman and that a wonderful man has just made love to me. I didn't know sex could be that good or that I could feel so much like a woman."
"Lucy you are a woman. It was wonderful to make love to you and I'm glad that I was able to. Just one hand on a back has led to all this!"