Andie arrived at the hotel around 4:30 p.m. He had received an email invitation a week ago and since then had vacillated between great excitement and serious doubts about the wisdom of coming. Still, ultimately it was an opportunity he just could not pass up. As instructed, he went to the main desk and asked if there was a letter for Mr. Underhill. The desk clerk passed him a plain white envelope. He opened it immediately and read.
A room has been reserved for you, 704. Check in as Mr. Underhill. Someone will stop by and help you get ready.
Andie was too nervous to eat and was worried about missing the person who was going to stop by so he went straight to his room and waited. He flicked on the TV but there was nothing that kept his interest. He tried to read a book he brought but couldn't concentrate. After brushing his teeth for a second time Andie found himself staring in the mirror and wondering just how had a guy like him ended up were he was.
It had all started about a month ago when he had been in a different hotel for a very different purpose. After a long day of mundane but useful business meetings Andie had come back to his room. It was late and, thinking that he would be undisturbed for the rest of the night, Andie decided to indulge himself.
After a warm shower he took from his suitcase some very special clothes, pink satin panties, a matching bra, a white lace garter belt and white stockings. He checked to make sure the blinds were closed and the door was locked and then slowly slipped on the panties.
As he had slid the smooth material up his legs his cock began to stir. By the time he was positioning the panties on his hips his full erect cock was too big for them and protruded above the lace trim. He slowly put on the bra, then the garter belt and stocking. Relishing the process.
Once he was finished Andie stared at his image in the mirror. Andie did not have a feminine face or body; he could not pass, nor did he fantasies about doing so. He was happy to be a man. Andie felt he had the best of both worlds. He did not let societies prejudices stop him for enjoying a world of soft feminine finery; he just kept it to himself. Andie was a man in panties and he found the perversity of it a great turn-on.
There was a knock on the door. Taken by surprise, Andie's heart began to race. Guiltless though he was, Andie was nevertheless deathly afraid of being caught. In a calm moment he'd tell himself that the intrigue was part of the fun, but at that moment he was imagining the horror of public ridicule.
Quietly as he could he ran to the door and looked out the peephole. It was the women staying in the next room; he'd seen her in the hall the day before. Andie was relieved that it wasn't someone he knew but he wonder why she was knocking, surely he hadn't been making too much noise.
She knocked again. "Just a moment," he said and regretted the minute he said it. He could have just kept quite but there was something intriguing about this woman.
She was dark haired and stocky. She was wearing a gray skirt and a light green sweater. That all he could make out through the peephole but he remembered that when he's seen her before he'd though she was quite attractive.
He dashed into the bathroom and tore off his lingerie leaving it in a pile behind the door. He pulled on a pair of shorts and t-shirt, paused for a second to caught his breath and opened to door. "Hi."
There was a self-conscious moment, at least for Andie, while she silently studied him. Then as she stepped into the room she said, "I'm Rachael, I am staying next-door - we met yesterday, may I come in." Not waiting for an answer she crossed the room and sat in one of the two chairs the room provided.
Andie was stunned and would have though the behavior rude except that he was distracted by the thought that she really was very attractive.
She was not a skinny teenage. She was, he guessed, in her mid-thirties. Her body was solid and shapely, large breasts and curvy legs, very sexy. Her hair was pulled back in a long braided ponytail and her eyes were noticeably green. Her skirt looked like part of a business suit. The jacket was probably on the back of a chair next door. She wore black panty hose and black low heel pumps. Her jewelry was all pearls except for a silver ankle bracelet.
She surveyed the room and then, pointing to the other chair, said, as though it were her room and Andie was the visitor, "Please sit down." "I'm sorry what was your name?" said Andie as he sat down. As soon as had Andie sat down, Rachael got up and walk briskly across the room. "Rachael," she said as she entered the bathroom. A second later she came out with the pile of lingerie in her hands. "These yours?" she smiled.
Andie was mortified. It had all happened so quickly. Unable to speak he just sat staring at her. After what seemed like hours, he began to stammer, "They're, I, uh.." Rachael interrupted, "I know they're yours, it's ok, I like it." Her smile widened, she was obviously enjoying this, but she wasn't cruel. "Really it's ok, I think it's great. I won't tell anyone." She looked earnest. "Look, I noticed the other day, when I saw you in the hall you were wearing a bra under your sweat shirt, I could see the outline of the straps."
I was true that late yesterday evening Andie had gone to get some ice and not wanting to change out of his lingerie he'd just pulled on a pair of sweats. He hadn't thought he'd meet anyone anyway; it was just down the hall. On his way back he'd seen Rachael exiting her room as he entered his. It had only been a second and the possibility that she had noticed something out of the ordinary hadn't even crossed his mind.
She continued, "I had a boyfriend who was a cross-dresser so I notice these things." She paused for a moment and when Andie, still frozen, didn't respond, she gave him a soft, sad look and said, "If you want me to go, I will and it will be like I was never here, but
I'd really like to see you with these on." Later on Andie couldn't explain why he did it but, for whatever reason, he then slowly stood up and said in a whisper, "ok." Rachael beamed at him as he took the silky clothes and walked it to the bathroom.
Andie pictured a press core of cameras waiting for him on the other side of the door. She's probably with the vice squad he thought. But he continued to dress. Because if it were true that this beautiful woman really would be turned-on by a man in lingerie and if she would join his sexual fantasy and wouldn't tell anyone, well it was an opportunity to good to miss.
Besides, he was caught already and by saying ok and taking the lingerie, he'd admitted to it. All irrational worries and foolish rationalizations aside, he was, in truth, propelled by lurid fascination and by raw lust.
When he was dressed, he looked at himself in the mirror and saw what he already felt. His cock was bulging; its head was bright red. He was so hard it hurt.
He opened the door and peered around the corner. Rachael was sitting on the edge of the bed, hands on her knees, waiting with obvious anticipation. Andie slowly moved his body into view. To Andie, who was feeling very self-conscious, it seemed that she almost laughed. She didn't, she just grinned and said, "Very cute, turn around." He did as he was told and when he faced her again, she said, "Do you like to be submissive?" "I don't know, I've thought about it but I've never tried it," said Andie truthfully.
Rachael pulled her sweater over her head. Andie could see her hard pink nipples straining against the material of her white silk bra. Her tone turned stern. "Get down on your knees and lick my tits," she said. Andie dropped to his knees before her and she leaned forward so that her large breast hung in front of his face.
He kissed and licked the top of her breasts, exposed by her low cut bra, then licked along the lace trim down into her cleavage. Sliding his tongue under the silky material he could almost touch her nipples. Rachael just moaned as he slipped her bra straps off her shoulders.
He peeled the bra down and put his mouth around her left nipple. "Oooo... suck my tits you slut," moaned Rachael. Andie massaged her tits with his hands while he switched between nipples with his mouth.
After a few minutes Rachael pushed his head back, stood up, discarded her bra, pushed off her shoes and dropped her skirt. To Andie's delight she was wearing not pantyhose, but lace top stockings.
Her white panties were damp at the crotch and through the wet material Andie could see that she had a think black bush of pubic hair, a few hairs were curling out from under the lace trimmed leg holes.
"Get on the bed and keep sucking my tits, my sexy slave girl," said Rachael as she laid herself out on the bed. "And sit where I can see you panty clad cock." Andie gladly jumped on the bed a resumed sucking Rachael's tits.
Rachael meanwhile slipped one hand into her panties and began masturbating herself while with the other she pulled Andie's cock out of his panties and began stroking him. Andie wondered whether he should do more but figured Rachael wouldn't hesitate to tell him if she wanted something so he just keep sucking and kissing her big saliva soaked tits.
Soon Rachael was squirming. She dropped Andie's cock and slipped her second hand under her ass. A few seconds later, Rachael was bucking violently as she brought herself to a string of climaxes.
Afterwards she lay still for a moment to catch her breath. Then she sat up, grabbed Andie cock, pushed it back into his panties and gave it a light stroke. Andie exploded. Cum filled his panties and trickled down his legs. It was the most pleasurable climax he could remember.
Andie's insatiable desire to cross-dress was driven by lust and it normally left him soon after his sexual tension was release by an orgasm. Usually, once he came, his concern about get caught in a compromising situation became utmost in his mind and he rushed to undress, cleanup, hide things away and get back to the safety of male clothes. This time however was different.
First, Rachael, in nothing but her stockings and wet panties, was sitting in front of him and she looked very pleased. The site of her sexy body and happy face removed some of his fear and almost immediately revived his sex drive. Second, he did not want to rudely rush Rachael out and give the impression that now that he had climaxed he didn't care about her. She was, he thought, an amazing woman and he was already hoping that they would be able to this again. So he said, "thanks," got off the bed, sat in a chair and waited to see what Rachael would do next.
She got off the bed and started dressing but when Andie got up to do the same she said, "No, stay there
I want to look at you in your cum stained panties." So, Andie sat and watch her dress and cock rose again.
"Your quite a sexy slut aren't you," said Rachael as she finished dressing. "Stay just as you are till I come back," and she left the room.
Andie's heart leapt as she opened the room door, if someone were see him like this he'd die of embarrassment, but no one was in the hall and for reasons he could not comprehend, around Rachael he didn't feel embarrassed. He had known her for all of half-an-hour and yet despite her stern tone she had been playful and kind and Andie trusted her; she had enjoyed it as much as he had.
His cock was shrinking, his cum was starting to dry and Andie was beginning to wonder whether Rachael would be back, when she came in. Again his heart jumped as the door opened but when he saw it was Rachael he was relived and glad that she had returned.
She carried with her a large black bag. She sat down next to him and drew her chair up close, so that they were face to face.
"I really enjoyed that and I'd like to do it again sometime, but there are a few things I've got to check out. Are you married?"
Andie shook his head no.
"Not right now," said Andie.
"Good!" she said and from the black bag drew out a test tube and a needle. Later Andie thought this should have worried him more than it did but he had decided to trust her and was still being submissive.
"It's ok, I've done this many times before," said Rachael as she took his arm. With a smooth action she pricked his arm and blood filled the test tube. She put the tube in her bag and put a band-aid on his arm.
"I want to make sure you're healthy. Here's a number." She handed him a slip of paper with a phone number on it. "Do you have safe email?"
"Yes," said Andie.
"Good, if you want to, call that number in two weeks and leave me your email address. If everything's ok, I'll contact you and maybe we can do this again."
As she stood up she pulled something else out of her bag. It was her still damp, white silk panties. "A gift," she said, handing them to Andie. "If you want to do this, you will have to limit yourself to masturbations until we meet again, ok?"
"No problem," said Andie.
Rachael smiled her wonderfully reassuring smile. "I'm checking out tomorrow morning so I won't see you again unless you call that number, I hope you do 'cause men like you are rare." With that she left.
Andie sat stunned for ten minutes before he cleaned up. By the time he had showered and got ready for bed he was wondering whether it had all been a dream. It must have been real; he had the phone number.
Two weeks later he had called. It was voice mail so he left a message saying it was Andie and, because he wasn't sure if she knew his name, saying that he enjoyed meeting her at the hotel two-weeks ago and giving his email address. The next day Rachael's email had arrived.
I'll be in the same hotel the weekend of the 5th. If you want to meet me there let me know by replying to this email. Before checking in ask the desk for a letter for Mr. Underhill. I would like you to check in before 5 p.m. on Friday.
Andie replied simply.
I look forward to seeing you again. I am at your service.
Now he was waiting nervously in his room, very much looking forward to seeing Rachael again but still concerned that it was just to good to be true. He worried that he might be confronted with blackmail or that some other nasty reality would turn his dream into a nightmare. Despite this he knew that like an addict he would pursue the dream at least until the cost of doing so was undeniably ruinous.
There was a knock on the door and as calmly as he could Andie went to answer it. Before opening it he took a quick peep through the doors peephole. He saw a woman with short blonde hair dressed in blue. He opened the door and said, "Hi."
"Hi, are you Mr. Underhill?" she said.
Andie nodded and stepped back so she could enter. She looked like she was in her mid twenties. With her she had a small purple back bag, the kind students used to carry their books around in. She very cautiously stepped in and Andie shut the door.
She was wearing a long sleeved velvet top, a knee-length flower-print silk skirt and sandals. She wore no stockings but are bare legs were smooth, even toned and beautiful without them. Below a thin gold chain her v-neck blouse exposed some freckled cleavage. Her breasts were smaller that Rachael but on her slim body they still looked enticingly ample. She had soft blue eyes and a pretty face but she looked nervous.
She looked down and, in a voice that sounded like a frail attempt to be assertive, she squeaked, "Take off your pants."
She looked surprised when Andie immediately obeyed and her confidence grew when she saw that he was wearing white silk panties, the pair that Rachael had give him. He had worn and washed them many times in the few weeks he'd had them.
"Rachael will be please that you wore them, she thought you would. I'm Sarah, Rachael sent me to help you get ready. Now take off the rest of those ugly male clothes."
Seeing Andie in panties had obviously made her feel much more in command of the situation and she visibly relaxed.
Once he was standing before her wearing nothing but the panties, she told him to get down on his hands and knees. Then from out of the backpack she pulled two disposable enemas. He got down on the carpet beside the bed and Sarah pulled his panties down.
"Why?" Andie stammer out but Sarah interrupted him, "Rachael likes everyone to be clean."
Andie was a shocked by the enemas, it was not what he'd expected but it was too late to back-out now, he was going for the whole ride. He might not like everything that was going to happen but whatever it was he'd survive; the precautious taking of blood was now a source of comfort.
Sarah lubricated the long thin tip of the enema bottle, kneeled down behind him. At first touch the plastic tip felt uncomfortable, but as Sarah pushed it slowly in the lubrication spread and the gentle pressure in his ass became a pleasant sensation. Then she squeezed the bottle and Andie could feel his bowels filling with water.
"You'll need to hold onto that for at least ten minutes, in the meantime lets get you into the bat room, you need to shave your legs," said Sarah standing up and stepping over Andie.
Keeping his butt tightly clenched, Andie stood up and shuffled into the bathroom. The bathroom had a walk-in shower with sliding glass doors and a shelf large enough to sit on. Sarah had him sit on the shelf and, apparently not wanting to get wet or, thought Andie, take off her clothes and join him in the shower, she had him run water over his legs and then turned the shower off. She slid back the glass door, handed Andie some shaving cream and told him to spread it all over his legs. While he did this she sat on the toilet seat and watched.
"Have you shaved your legs before?" she asked.
"Yes," he replied, "once or twice but not very often." Taking this as proof of competency in the art of leg shaving she handed him a pink razor. Slowly and very carefully Andie began. Sarah watched in silence while Andie shaved.
Much to his surprise he manage to finish the job cut free. As he finished up Sarah asked, "Why do you want to be a woman?"
Andie stopped and looked up. "I don't want to be a woman, I just enjoy doing some feminine things; it turns me on."
This was not the answer she had expected. She had a look of doubt so Andie continued, "really, I like being a man and I don't want to change. I just like wearing lingerie and stuff."
"Are you gay," she asked.
Andie had thought that at some point Rachael would ask him questions like this but he had not expected to be questioned under these circumstances. Still, Sarah looked seriously interested and he had considered how he would answer a question of orientation.
He though that it should be obvious that he wasn't completely gay but maybe Rachael hadn't told Sarah much about their first meeting.
"I'm not gay, I like women." he pause then said, " I've had homoerotic fantasies but I've never actually had a homosexual encounter, so I guess I'm maybe bi." He couldn't be more honest than that.
This answer seem only to increase Sarah's curiosity and she continued, "Well what about wearing lingerie turns you on?"
"I don't know, I've always done it
I mean I have some theories but really I don't know," said Andie. "Uh, Sarah, it's been at least 10 minutes and I really need to go."
Sarah got up and left the bathroom while Andie relived the pressure in his ass. He washed himself off in the shower and putting a towel around his waist when out to see Sarah.
"Why so shy," said Sarah commenting on the towel. She came over and pulled it off. "I've got to give you another one of these anyway," she said and held up the second enema bottle. When Andie groaned she said, "Well now that I know you'll appreciate it maybe I'll make it a little more exciting," and with that she took of her top.
She was wearing a bra of shear material so that her nipples could be seen quite plainly. When Andie's cock started to raise Sarah smiled. This time she had Andie lie on his back with his legs propped up by the bed. She stepped over him so that as she applied the enema, Andie could look up her skirt.
While Andie tried to make out the folds of her pussy beneath her sheer panties, she lent over, dabbed a little lubrication on his ass, slipped the bottle's long tip in and squeezed. Water filled Andie again. Sarah pulled out the bottle, stepped back and asked, "So, how long have you been wearing women's clothes?"
Still lying on the floor Andie answered, "Since I was 10."
Sarah sat down on the edge of the bed. "Really?" She looked puzzled.
"Do you want me to tell you about it?" said Andie, this was a story he never got to tell, it might be fun to tell someone and Sarah already knew the worst of it; or the best of it, depending on your perspective.
"Yes, tell me." She lifted her feet onto the bed and stretched out, propping her head on one arm so that she see Andie lying below. Andie felt like he was at a very bizarre slumber party and that it was his turn to tell a story.
"As far back as I can remember I had dreams and day dreams of being made to wear girls clothes. In my earliest fantasies an attractive female teacher would, in front of the class, make me switch clothes with one of the girls. Then I'd be tied up and put on display. Sometimes I'd be made to lie on the floor while each of the girls in class would in turn come up and piss on me. I don't know why I had such fantasies and at the time I didn't question them but I did know enough to keep them to my self.
The first time I actually wore lingerie was as I said when I was about 10. I was alone in the house, which was not uncommon, when I noticed that hanging on the back of the door in the upstairs bathroom was a sexy negligee. It was baby blue silk with an outer layer of white lace and chiffon with ruffles alone the bottom edge. I was transfixed; I remember it well.
I locked the door, stripped of my clothes and slipped it over my shoulders. It felt wonderful. It made me feel warm all over, so soft and beautiful; at first it was very relaxing.
I looked at myself in the mirror and liked what I saw but then doubt creped in and I thought about how horrified my parents would be if they caught me this way. Then I was overcome with shame. I quickly pulled off the negligee, dressed and then anxiously tried to remember exactly how it had been lying against the door. I waned to arrange things as if nothing had happened.
The rest afternoon I nervously waited for my parent to come home. Later that day my mom went into the bathroom and I was sure she would notice something but of course she couldn't tell. They weren't particularly observant anyway but you know it would have taken a detective to notice anything. Still, for a while the fear kept me from doing it again but it had felt so great that eventually I did tried it again and I've been doing it ever since."
Andie had been looking at the ceiling while he'd been talking but now he looked at Sarah. She didn't look horrified. He had though about his cross-dressing story many times but had always pictured the telling as a confession of his sins. He'd pictured a jury getting increasing horrified as he went on and in the end condemning him as an incurable pervert and sentencing him to life long ridicule and banishment. Sarah didn't look condemning, just interested and since she didn't speak during the pause he went on. It felt good to actually talk about it, especially so because the reaction was not what he had feared.
"I don't know why it felt so good. I guess it doesn't really matter. But I have thought about it and, as I said before, I have a theory.
My Dad was, in his own way, a very macho guy. He had very ridged ideas about what a man should be like and as soon as I could talk he expected me to be a man. He didn't go in for expressing feelings and made it clear that he thought feelings were for women and babies. He was also a big war buff, not the John Wayne, good guy, bad guy stuff but brutal real war stuff. He would read to me books about World War I and show me documentaries about Stalingrad and the Holocaust, when I was like seven or eight years old. I think somewhere down the line I got the idea that it was a man's lot to go to war."
Andie paused and looked at Sarah. He noticed her raised eye browse and quickly added, "I know a lot of guys have Dad's like that and they don't go jumping into a dress but I think it was, at least a first, the way I coped. I think it kind of took the pressure off, you know, if I was a girl I wouldn't have to
" Andie trailed off.
Sarah had sat up and was looking at him in a funny way.
"Excuse me, I got to go to the bathroom," said Andie. He carefully stood up and went to the bathroom. Sarah still said nothing.
Andie released a stream of almost clear water into the toilet. Afterwards he jumped back in the shower and washed completely. Then he got out, dried off and looked in the mirror. He could see his face needed a touchup shave.
"I going to shave my face, ok?" he yelled.
"Sure," said Sarah.
When he was satisfied he came out, this time naked. Sarah was still lying on the bed and looked deep in thought. Andie was now worried that maybe he'd shared too much but felt compelled to continue because he didn't want to be misunderstood.
"It's just a theory, I haven't have seen much of my Dad for years and I still to it, so maybe that just an excuse."
"You don't need an excuse, it is a little strange but it's not against the law," said Sarah softly.
"That's what I think but it's still something that I wouldn't want everyone to know about. It's just another sex fetish, a lot of people have them but they keep them private, right." Andie sounded a little defensive.
"Sure," said Sarah nodding her head. Andie had something to get off his chest and Sarah seemed content to let him do it.
"It always felt kind of sexy but it wasn't a sex thing at first, I mean I didn't fantasies about having sex when I dressed up. Anyway, after getting over the fear of the first time, I began to borrow my mom's underwear on a fairly regular basis.
The lingerie that I was most attracted to was kept in a storage box in the back of her closet. It was stuff she must have worn when she was younger; it was smaller and sexier than her everyday underwear. By the time I was borrowing it, I doubt she ever used it; she didn't seem to miss anything or notice that anything had been moved.
When my parents were out I slip into a pair of panties and a bra or camisole.
As I got older I did it more often and it got to be more and more entwined with sexual fantasy.
One time, I must have been twelve; I'd pretended to be sick so that I could stay home from school. Both my parents worked so I had the whole day to myself. I was wearing a corset, panties and high heel shoes. I knew nothing about masturbation but I had a hard-on and it felt good to rub it, I thinking about a cheerleader that I found particular attractive when much to my surprise I had my first climax, got cum all over the carpet."
"I was a cheerleader," said Sarah.
I'm sorry, I'm going on."
"No its ok, I'm interested and Rachael did tell me to take sometime to get acquainted, so tell me more, did you every get caught?"
Andie who had been leaning against a dresser, sat down.
"I have never been caught in the act, so to speak, but looking back I think my parents must have known. As I got older I took more risks. Eventually I got tried of my mom's old stuff and started borrowing lingerie from the laundry room in the apartment building we lived in. We moved out of the house when I was eleven.
I'd steal a pair of panties or something and hide them my room until bedtime, then I'd put them on under the sheets. Most of the time I'd end up masturbating then I'd clean up and re-hide the stuff but more than once I fell sleep still dressed.
Maybe they knew, maybe they didn't, but I wouldn't put it past them to know and ignore it. They were very good at ignoring things.
I had a girl friend that knew. We were both sixteen. We used to play a lot of sex games, like strip poker and truth or dare, well I eventually steered things into switching underwear and it turned out she liked it.
We'd be out somewhere and we'd find a place to switch, it was great I'd put on her panties and could feel were she'd gotten them wet with anticipation. I took to wearing her panties whenever we had sex; she even bought especial sexy panties just for me to wear. Eventually we broke up, believe it or not her mom was pressing us to get more serious and I couldn't take it.
The next girl friend I had let me wear her panties when we had sex but it was an act of tolerance, she didn't like it, thought it was weird and when she broke up with me I always wondered whether it had anything to do with it. After that I decided I'd keep it to myself and told no one about it until Rachael came along."
"How did you meet Rachael?" asked Sarah
Surprise that she didn't already know, Andie told how he met Rachael. Then he felt that he had talked enough. He'd just told his darkest secret to a complete stranger and though it felt good he now wanted to know about her. It seemed only right that she should now share with him. So Andie said, "Well, that enough about me, what's your story Sarah?"
"You mean how I met Rachael"
Sarah pulled herself up so that she could lean her back on the headboard adjusted her skirt, smoothing out the blue silk, and when she was comfortable she began.
"Well when I was in college Rachael was my landlord. She owns the house I lived in. It was a three flat and I rented the garden apartment. At the time, this was a couple of years ago; Rachael lived in the main floor apartment. Well, on the same floor as my apartment was the washer and dryer that everyone shared, there were also some people who lived above Rachael. There was a door on the back of my apartment that leads right into the laundry room.
One day Rachael was doing some laundry and for some reason she decided to see if I was home. She said she'd knocked but I guess I didn't hear, I had music on, so she tried the door and I must have forgotten to lock it because she came right in. Well, I was, you know, having fun with myself." She looked at Andie sheepishly. Andie guessing what she meant but wanting her to be more explicit gave her questioning look.
There was an uncomfortable pause then, apparently deciding that she should be straightforward she said, "Ok, I was fucking myself with a vibrator." As soon as she said it Andie felt more relaxed. He also felt his cock coming to life. "I was completely naked, stretched out on the couch and I was looking at a Penthouse magazine. I'd always found beautiful women a turn-on but I'd never acted on it except in private. I also like guys and I'd had boy friends, I had one at the time, but every now and then I'd masturbate with pictures of women. Rachael saw everything; it was a small place only two rooms so she had the full view the minute she walked in. Of course I was surprised and tried to cover up and was apologizing and stuff. I didn't know what she'd think and I didn't want to get kicked out.
She took it in stride, like she was expecting it, she pick the magazine up, flipped through it and said "beautiful naked women turn me on." Then she looked at me and said, "mind if I join you?" I said no and she started taking her clothes off. It was so exciting. We looked at the pictures and at each other and finger fucked ourselves. She didn't want to do too much, as you know she's real careful, but it was ok with me, I'd never actually been with another woman and I didn't know how far I wanted to go anyway. She did let me suck her tits. When I saw her next she asked if I wanted to do it again. I said yes and that's when see took my blood, she's a doctor you know.
A couple of weeks after that, she called and asked if she could stop by, on the coming Friday night. I was very excited, I didn't know quite what to expect but I knew Rachael would lead me.
When she got there she was wearing a long coat and had a large bag. She asked me to relax on the couch while she used the bathroom. When she came out she was wearing all black, thigh high leather boots, a leather corset and a lace thong. The lace trim of her corset came to just below her nipples, the lace tops of her stockings rose a little higher than her boots." Andie noticed that Sarah's nipples looked like they had perked up and that, as she described Rachael, she was shifting her legs against each other; she was getting turned-on. Watching her, Andie's cock stiffened. "She was so beautiful and so powerful I did everything she asked and have been her devoted sex salve every since."
"We'd better get ready Rachael wants us to be there at 8 o'clock," said Sarah. She slipped of the bed and walk over the dresser. From the top draw she pulled out a camisole, matching panties and garter belt, and white stockings. "These are for you," she said and lay the carefully out on the bed. Andie picked up his panties. There were shiny blue satin and had a lace front panel. He pulled them on and when the silky material uncased his crotch his already semi-erect cock hardened so that it was barely contained by the bikini cut panties. Next pulled the garter belt around his waist and slipped the straps under his panties. The he pulled on the stocking and attached them to the garter straps.
All the while Sarah watch with fascination. When he looked up she was smiling at him. "It's strange to see a man in lingerie but its kind of sexy in a real kinky way." Andie, who was most certainly felt sexy in a real kinky way, took this for a compliment and said, "Thanks." He pulled the matching camisole over his head and sat down to enjoy being dressed and to watch Sarah dress.
Sarah slipped off her silk skirt. Her panties matched her bra and Andie could clearly see her blonde bush through the lace-trimmed chiffon. Realizing that Andie was enjoying watching her she held up her hands as if to say "Ta Da!" and he clapped. She reached behind her back and undid her bra and let it drop to the ground; then her swiftly pulled off her panties. She was quite beautiful, tan and health, her body firm and energetic. Andie thought that she must have spent time outside in the nude because she had no tan lines and he had the feeling she was not someone who would use a tanning salon.
Sarah lingerie was in the second draw. She pulled out a pair of white lace panties and slipped them on. Then she put on a satin white bustier, lace top stockings and a lace chemis that tied in the front with bows. As a finishing touch she put a white silk bow in her hair. Andie though she looked like a particularly hot bride on her honeymoon night.
"It's time to go," said Sarah and from the closet she produced two long coats. It occurred to Andie that even with a coat if someone saw him they would have to be two observant to notice that he was wearing stockings. "How far are we going," he asked.
"As far as Rachael what's to take us," said Sarah with a giggle, "but right now just down the hall."
Sarah checked the hallway. "All clear," she said and they both headed out. To Andie's relieve they had only a few feet to go and with a few seconds they were entering room 700, Sarah hadn't bothered to knock.
Room 700 was actually a spacious suite. The room they entered had a lounge set in front and a desk to one side and in the back surrounded by windows and on a raised platform a large in-ground whirlpool bath. The floor-to-ceiling windows were covered by long sheer drapes. In the middle of the lounge set was what looked like a wrestling matt cover by a velvet sheet. Rachael was sitting at the desk; she got up as they came in.
Rachael was wearing a silk dressing gown, black and decorated with dark red roses. Her long black hair was tied back in a loose braid. Around her neck was a diamond studded black leather choker and black leather high heel boots covered all of her legs that could be seen beneath the dressing gown.
"Take off your coats," she said with a mischievous smile, her green eyes glinting. Sarah and Andie took off their coats. Rachael put her hand on Sarah's chin, drew Sarah face to hers and gave Sarah a passionate kiss on the lips. "You look beautiful Sarah," she said. She turned to Andie and said, "I'm glad you came, you look deliciously sexy." Then she gave Andie a similar kiss, then drew back to take a longer look at Andie. She stroked her hand on the front of his panties, along the length of his hard cock and said with a sly simile, "This is going to be fun."
Stepping back she let her dressing gown fall to the ground. This reveled her large bare breasts. She was wearing a braless bustier made of the same material as the dressing gown and trimmed in black chiffon ruffles. She was also wearing, what Andie suspected were, crotch-less black lace panties.
"Come over here," said Rachael pointing to the mat as she sat down on the couch. Now Andie had no doubt that Rachael's panties were crotch-less, when she sat down she opened her legs and reveal her already glistening pussy.
"Andie kiss Sarah's legs."
Sarah stood in the middle of the matt. Andie drop to his knees in front of her and began by kissing her feet. He slowing worked his way up, switching between legs as he when. When he had almost reached the trim of Sarah's panties, Rachael suggested, "Pull her panties down and lick her cunt Andie." Andie pull them down to her feet and Sarah stepped out. Then she sat down on the mat and opened her legs. Andie took his time, teasing her before he buried he tongue into her.
"Sarah come over her and suck on my tits, Andie you keep licking her," commanded Rachael. So Sarah turned over and crawled to her. Once she was positioned on all fours sucking Rachael large tits, Andie came up behind her and began licking her clit.
Sarah kept switching between Rachael's tits and cunt and was squirming around so much that Andie so found him self with his nose in Sarah's ass. He could only breath through his mouth when he took a quick break from licking. Sarah seemed to be deliberately pushing her ass into his face. Apparently Rachael noticed this because she said, "go ahead lick her asshole, she loves it."
Andie used one hand to massage Sarah's cunt while with the other hand he spread her ass checks. He started by gently licking around her puckered hole. Then he put the tip of his tongue against her asshole. She pushed against his tongue so he pushed it into her hole. Soon he was flicking his tongue in and out of her, on the inward thrusts pushing as deep as he could go.
Meanwhile he was also giving Sarah a good finger fucking and after a few minute of this Sarah began to shudder. She stopped licking Rachael and let her head drop to the floor. While balancing with one hand she used the other to grab Andie's hand and push it more forcefully into her now streaming pussy. "Keep licking my ass," she moaned as bucked so violently that Andie had a hard time staying in place.
Eventually, after what Andie guessed must have been several orgasms, Sarah collapsed. When Sarah had pulled away from her, Rachael had grabbed a large purple dildo from a draw in the table next to the couch. While Sarah climaxed Rachael watched with excitement and fucked herself with the dildo.
Then Rachael beckoned Andie to her and moved down the couch out of Sarah's way; Sarah, breathing hard, her hand still on her wet bush, was recovering. "Come lick me, sexy slut," said Rachael to Andie. Andie licked Rachael till his tongue was aching with fatigue and was relived when she said, "Take you cock out of your panties, lets put your assets to use, girl."
Rachael slipped of the couch and positioned herself on all fours so that Andie could fuck her doggy style. Andie pulled his panties off and positioned his cock between the folds of Rachael's dripping pussy. Slowly he guided himself into Rachael, her tight warmth made his cock pulsate, and then he bent over her back and grabbed hold of her hanging tits. "Oooh yes, squeeze my tits and fuck me you sexy whore," yelled Rachael Andie pumped quickly a few time and then, feeling himself cumming, slowed down, he thought Rachael might be unhappy if he came so soon, but Rachael yelled, "faster, fuck me hard, you bitch." So Andie fucked her with his full force, bringing his cock almost out and then, pulling on her tits, driving in hard, so that his thighs smacked loudly on her ass and he could feel her juices splash onto his legs. It didn't take much of this before Andie reached the point of no return and tightly clutching Rachael he filled her pussy with cum.
After a pause to catch his breath Andie tried to start again but he had softened a little and he knew it wouldn't feel the same. Rachael pulled away and turned around but she didn't seem upset, rather she had a mischievous simile. "Lick my cunt," she said with a look like she was daring him to do it. Andie hesitated and Rachael said, "be a good girl and suck the cum out of my pussy." I want to do it thought Andie and the only reason I hesitate is I'm worried about what they'll think of me, but Rachael wants this and I am hers to command. Andie lower his head and licked Rachael's cum filled pussy. It tasted a little salty but pleasant. "Mmm, that's it, suck it all up" moaned Rachael. Soon Andie's face was covered in a mixture of Rachael's juices and his own cum, and his cock was hard again. "Sarah," said Rachael as she leaned back "get the blue dildo and put it in my ass - and get the pink plug for Andie."
Sarah pulled from the table draw a small pink but plug and a translucent blue dildo both made of soft flexible plastic. Sarah poured perfumed oil over both of them. First she pushed the butt plug into Andie's tight ass. She had to push hard and it hurt a little going in. Andie, who was trying to keep his tongue in Rachael, found his face being pushed hard into Rachael's crotch. Once it was in there was no pain and Andie found the pressure in his bowels stimulating. After placing a pillow under Rachael's hips so that she could access her ass while Andie continue to lick her, Sarah pushed the dildo into Rachael's asshole. It was the shape of several balls attached together on a long tube. "Aahh," exclaimed Rachael each time a ball penetrated her ass. "Give it to Andie and suck on my tits," breathed Rachael between moans. Sarah put the end of the dildo into Andie's hand and continued to slowly move it in and out of her ass while Sarah moved up so she could suck on Rachael's large heaving tits.
Rachael shuddered then she clamped her leather-clad legs around Andie's head and began rolling back and forth. Andie let go of the dildo, which was buried deeply in Rachael's ass, and was only just able to catch a breath as she used her legs to ground his face into her sopping crotch. Finally when both Andie and Rachael were completely out of breath Rachael came to a stop and fell limp.
Andie lifted his head and Sarah, now re-energized, kissed him, long and hard, on the lips and all over his face. Then she bent down and took his hard cock into her mouth. While she held his shaft with a firm hand she sucked hard on the dark pink head of his cock. Then she stood up, slipped off her chemise so that all she had left on was her satin bustier, and with Andie still kneeling mounted his aching cock. Andie pull the straps of Sarah's bustier off her shoulders and pulled the lacy white cups away from her breasts, the nipples on small firm tits were hard and pointy. While Sarah moved herself up and down on his cock Andie lowered his head a little so that he could lick Sarah tits and suck on her up turned nipples.
Sarah kept this up for quite a time but, either because her legs were tiring or because she just wanted a change of position, she rolled over on her back so that Andie could take a turn at the work. This he was glad to do, he was almost ready to cum again.
By this time Rachael had recovered and she moved herself over Sarah so that she was facing Andie and that her still oozing cunt was right over Sarah face, a glob of white dripped onto Sarah's lips. Sarah opened her lips to let it slide into her mouth and began shaking. "Don't cum inside her," said Rachael; correctly interpreting Andie's face, "I want you to cum on my tits." With no time to spare Andie pulled out of Sarah, who immediately replaced him with her fingers so that she could continue her climax, and pushed his cock towards Rachael's tits.
His first burst hit Rachael just below her neck, rolled down between her tits, over the chiffon ruffle of her bustier, down the front of her bustier, staining the black and red satin, and into her dark pubic hair. His second burst hit Rachael on her left nipple and dripped onto Sarah's stomach, staining Sarah's bustier. Then he let go of his cock and it snapped back onto his chest and oozed a final wad of cum onto his camisole. Andie had successful got cum on everyone, which surprised him because he rarely came that much on his first climax let alone his second.
Sarah was spent and Andie's cock had given all it could but Rachael was still hot. Knowing she would now get limited assistance she grabbed the large purple dildo, the blue dildo was still in her ass, and shoved deep into her cunt. "Suck my nipples," she commanded and while Andie sucked on her nipples she aggressively fucked herself. After had she brought herself through a wave of orgasms, she pulled out both toys, let Andie collapse and then she too came to rest.
They lay in silence for several minutes. Rachael was the first to speak. "Andie, please fill the bathtub halfway with cold water," she said. Andie was unsure why Rachael wanted this but by now he was ready to do anything Rachael asked for. He found the bathroom, just off a corridor leading to the bedroom, pulled the butt plug out of his ass and sat on the edge of the bath while it filled. A minute late he found out why she had wanted it. Rachael and Sarah stripped off and threw their soiled lingerie into the tub. "Throw your stuff in and join us in the whirlpool," said Rachael. Andie hurried to join them.
By the time Andie had stripped off and come out of the bathroom, Rachael and Sarah had both already gotten in and dipped their heads underwater, so they now sat relaxing, their hair wet and slicked back, the frothy water lapping at their chests. Andie found the water already hot and slowly eased himself in. Once in he quickly adjusted and, dipping his head underwater, rubbed off the residue of juices from their sex play. Then he too leaned back and relaxed.
"So, Andie are you glad you came," said Rachael.
"Yes I am," said Andie with gusto.
"And Sarah, are you glad Andie came."
Sarah paused and looked at Andie. Andie had sensed something like reluctances in Sarah when he'd first met her but there had been nothing reluctant about her since they'd been with Rachael. Maybe her enthusiastic performance had been an act for Rachael or maybe she had just been caught up in lust. For the first time he realized that this had also been an audition for Sarah and that if she was not comfortable with him he might not be invited back. His face must have reflected some of his concern because Sarah gave him a reassuring simile when she said, "I'm glad he came."
"Like I said, men who will wear panties are different," said Rachael to Sarah, "for some reason when a man puts on lingerie it deflates his ego and make him more willing to be lead by a woman. They also become less self-centered and sex for them is not so much about getting to a climax." Rachael turned to Andie and asked, "What do you think Andie?"
"I don't know," said Andie. "Maybe men who are willing to be led by women are more likely to want to wear lingerie than other men."
"Well either way, a willingness to cross-dress is an indication that a man is more likely to be willing to be led in sex play by a woman, at least that's been my experience," said Rachael.
"I think Andie's more than willing," said Sarah her simile appearing again; Andie was already becoming fond of her simile.
"I have always had a strong desire to cross-dress and have needed no encouragement to do it," said Andie.
There was a pause then Rachael said, "Maybe along with a desire to be personally adorned with symbols of femininity comes a respect for feminine power."
"In your more thoughtful cross-dresser," said Andie, nodding. At this both Sarah and Rachael laughed.
They sat in the whirlpool quite sometime, longer than recommended, the water jets were on a timer and Rachael renewed it twice. They talked about everything from sitcoms to impressionist painting, Andie reveling a preference for Degas and Sarah a dislike of Hollywood's avocation of skinniness. Andie agreed with Sarah's opinion on excessive skinniness but though it was odd that Sarah, who though not excessively skinny was quite trim, should be the one to express it, he thought it was something more likely to come from Rachael. Well, I guess I don't know them that well yet, thought Andie, but he was feeling like they were old friends.
When the timer ran out for the third time Rachael decided it was time to get out. There was a pile of towels next to the whirlpool and each took one and dried off before Rachael led them to the bedroom. The bedroom was large. In the middle of the room was single king-sized bed, covered in satin sheets and a satin comforter. A large mirror hung on the ceiling above the bed. That's the kind of ceiling that can be exciting in the evening and disturbing in the morning, thought Andie.
Rachael open one of the room closets and reveled three pastel-colored long satin night dresses. She handed the yellow one to Sarah and the blue one to Andie, hers was green and when she had slipped it on Andie noticed how it brought out her eyes. They were all lace trimmed but they were cut differently. Rachael's had more room for her large bust and a plunging neck line that showed off her cleavage. Sarah's was of shorter length, showing off her beautiful legs, it had spaghetti straps and the light yellow color accented freckles on her shoulders, very cute thought Andie. Andie's had a high neckline, though not so high that it was uncomfortable, and was obviously made for a women with very small breasts, which, as Andie had no breasts at all, worked well for him.
Rachael got into bed first, Sarah and Andie got in on either side of her. The satin on satin felt wonderful. Looking at the three of them in the overhead mirror Andie marveled at his situation, in bed with two incredibly sexy women and they were encouraging him to indulge his most secrete sexual desires. He realized that it had been over fifteen years since a woman had seen him in lingerie and that he had thought throughout that time, that if one ever did, their revulsion would be a source of unbearable humiliation and yet here he was experiencing not humiliation but joy. His head nestled against Rachael's bosom Andie quickly fell asleep.