Ask a sugar baby - Alice
How does a teenage girl become a sugar baby?
Alice 19 is a sugar baby . “ I was working as an escort when I met my sugar daddy. He was a punter who became a regular client, he became infatuated with me, always asking why I was selling myself so cheaply as an escort. A lot of men feel that they want to rescue a working girl, so I just thought he was a guy who wanted to be a knight in shining armour to me. One day he offered to take me out to dinner, I accepted but told him that I charge by the hour for this service and that if he wanted sex after that would be extra. Little did I know at the time that he was taking me to the apartment that he had bought for me, I couldn’t believe it, I was a 19 years old teen escort and some regular punter had just bought an apartment for me.
Is being a sugar baby better than being an escort?
Well yes, I now only have sex with a few men every month but I can do whatever I want with the rest of my time, I no longer have to have sex with lots of different men every day as an escort .
How much money should a sugar daddy give you?
That really depends on how wealthy he is, I have a sugar daddy who is extremely wealthy, a multi-millionaire in fact. He gives me a monthly allowance, has bought me an apartment and pays for driving lessons, when I pass my driving test he will buy me a car. Being a sugar baby has really opened my eyes to how mature men behave towards young girls when they have a lot of money, they really like to lavish expensive presents, it makes them feel good, it also keeps their sugar baby interested in them.
How do you meet your sugar daddies?
There are various social media sites and specialist websites where younger women go to meet (hopefully) wealthy men who are looking for a girl to keep as a paramour, which is really what a sugar baby is.
Do you get lots of offers from men when you put your profile on these websites?
Loads! A lot of the guys just want a one night stand with a teen sugar baby, they promise you the earth but then don’t deliver. I have been caught-out in the past by men who just want to take me to dinner, then expect a quick fuck. But I soon learnt that you have to be patient and never have sex with a potential sugar daddy on the first, or even the second date. That way you get to see how committed he is. Once you have the right guy, you can then put all your energy and effort into seducing this one man.
Why do you think that men of a certain age want a sugar baby?
It’s a power- thing. It’s also a win- win for both parties. The man gets to feel that, in some ways, he owns you, he takes care of you. And in return, he gets the pleasures of a girl that he couldn't get if it wasn’t for the fact that he is wealthy. For the girl, she gets everything in life that a girl wants. Clothes, jewelry, apartments, cars, and she doesn’t have to work. The only thing she has to do is to make her sugar daddy feels he is the only man in her life, and to let him fuck her of course.
Ask a sugar baby - Jemima
How did you become a sugar baby?
Jemima is 21, a well-educated young socialite . “I first got into the sugaring scene when I was at Uni studying fashion 2 years ago. I was in a bar with a friend when a mature man, well into his 60’s asked if he could buy us a drink. We accepted and got chatting, to cut a long story short the next day he called me and offered to take me shopping. What girl could refuse! I was hooked. I am now a full time sugar baby with 3 different sugar daddies in tow, each one is a married man, they’re the best because there are no strings, they just want me when they are available, maybe once a fortnight and always bring me gifts, plus they keep me financially solvent, very solvent.
What do your friends think about your sugar daddies?
Some of my friends liken my activities with my sugar daddies as being nothing more than a prostitute, but as I tell them, being an escort or prostitute, I would have to visit lots of different men in their hotels and they would be in the driving seat. As a sugar baby, it is me that is in control. My sugar daddies are only too happy to keep me happy, so they go out of their way to make sure I am content with the relationship”.
Do many sugar babies have more than one sugar daddy?
“If they’re clever, yes! As I said earlier, the best sugar daddies are wealthy married men, they are not looking for any long-term commitment, there is no pressure, and any moment we spend together, whether in a hotel room or out shopping together is time that we both enjoy. That fact that he goes home to his wife is ok by me, and it gives me the freedom to see my other sugar daddies. It’s a win-win situation”.
How much money can a sugar baby make in a month?
“I don’t really look at the relationship in terms of finance, or how much they give me, but living in a two bedroom apartment costs a lot of money. My number one sugar daddy bought my apartment for me last year, and furnished it for me. He also gives me an allowance, I’m not telling how much, but he is a very generous man and I like him a lot. My other sugar daddy has just bought me a new car and also pays for the insurance. “I’m a lucky girl”.
Do your sugar daddies know that you see other men?
“God no! That would be a disaster”. Every sugar daddy has to think he is the only one.
Racheal is an upscale black escort. She won many beauty contests.
What made you become an escort?
As a black girl with no formal qualifications there aren’t that many opportunities for employment with any sizable income, so short of finding a rich boyfriend my only real option to make a decent living was to become a call girl or work as a massage girl .
How did you start?
Well, I started working the streets, prostitutes are always available 24/7 but the problems with punters and the police were making life difficult. And you have to know that I was only a young woman at the time and I knew very little about the escort agency girls and how much better it was to work in a more constructed environment.
Are black escorts popular with clients?
Yeah, especially with middle class white guys. Most of my regular clients are white married guys and nearly all of them have never even seen a black pussy before, let alone a black girls tits, they love it. Imagine being 50 years old, married to the same white woman for 25 years and then tasting your first ebony escorts pussy for the first time; heaven right!
Why do you think that is?
Most white guys never get the chance to sample the delights of a black girl in their normal life so if they have a penchant for a black girl their only real option is to hire black escorts . I’ve had lots of guys want to take me out for dinner, I think they get a big thrill by having a beautiful black girl on their arm and when we go to a fancy restaurant we do get lots of looks.
What is the most requested service that men want from call girls?
Oral without a condom is the number one. Number two is nearly all the clients that I see want to taste a black girl's pussy, I’ve lost count of how many white guys say that black pussy tastes different to white pussy. They also like to have a black escorts go down on them and they all want to cum in a black girl's mouth. Of course all men today want oral without, which is okay by me.
How has working as an escort changed your attitude towards men?
Not at all really, even though I’m still quite young, just 21, I’ve always known that boys and especially boyfriends will mess around with other girls if they get the chance. I don’t think it’s in men’s nature to be totally faithful to one girl. You only have to listen to a group of men talking in a bar to know that most of their conversations are about girls they’d like to fuck or women in their office they fancy. So it’s no surprise to me that married men hire escorts or visit massage parlors .
Do you think that married men who visit female escorts are cheating on their wives, or is it a harmless bit of sexual fun?
Well there are two answers to that question. If you ask the husband if he thinks hiring escorts is cheating he would probably say no, it’s just a bit of harmless pleasure. But if you asked his wife the same question she would probably say absolutely, he’s a dirty rotten stinking scum sucking piece of pond-life, and he go fuck himself if he thinks that he can get away with fucking prostitutes without any comebacks.
Do call girls have boyfriends?
It’s quite difficult to have a relationship with a normal working guy when he knows that his girlfriend is a visiting escort or giving hand relief and blowjobs to clients in massage parlors, I mean what do you talk about in the evening? How many guys did you have sex with today honey? It’s really not possible to have a traditional relationship with a boyfriend. I do know some escorts that have boyfriends, but they are few and far between. Most girls want to make as much money as they can and then try to live a normal life, once they have given up working as a sex worker.
My Night With A Thai Ladyboy
I am a very straight guy. I’ve never been turned on by a man in the slightest way. I have a couple of gay friends who I am completely comfortable around. But no matter how “good” they look when they’re all dressed up I never think anything other than, “how funny, he’s trying to be pretty, but he’s still an ugly man.” So my initial thought when my girlfriend suggested we go to see a ladyboy cabaret during our vacation in Thailand this summer was “what’s the harm”.
We showed up and a squadron of men in drag were lined off outside, in full costume like it was the Brazilian carnival, wooing customers for the show that was about to start. They were all obviously men, and no amount of makeup had changed that. I was neutrally surprised, since I had heard so many stories of the indistinguishable Thai ladyboys. Anyway, I knew the cabaret would be pretty mild and nothing like a sex show, so I didn’t really care.
We went in and the show started, with obviously manly participants. A couple were pretty and had feminine faces, but I always saw them as men. I started to become aware of the tiny details of femininity which were often a giveaway. Bony knees and ankles, large shoulder blades (or was it muscles?), and something about the cheekbones and the jaw. They pranced about onstage performing routines that would have been risqué in the 20’s. It was pretty good entertainment, and fairly harmless. At one point they were wearing thongs. The nudity gave me the kind of feeling that you get from seeing a muscle chart in a biology book. “Oh, buttocks”.
As the show went on, the waitress came over, a young thai girl with a pretty, round face. We ordered some (expensive) drinks and continued watching. As the show progressed I started to get confused. Some of the ladyboys had feminine figures, feminine faces and virtually no masculine features. Two were very pretty, and rather sexy. I found it funny that I thought so, and told my girlfriend which ones I liked.
Eventually, the show wound up. The DJ switched to party hits, and some rubes from the crowd got pulled on stage. The music was actually pretty good, and we started dancing too while we finished our third round of beers.
Eventually, everyone had left and it was just us dancing. The ladyboys who were still around came over to dance with us. One was older and one was fairly overweight, and one was the waitress I had thought was a girl. She said something to us in a soft, feminine voice. But there was no mistaking it - she was definitely a ladyboy. I found her so sexy that the realization threw me off. I actually felt somewhat repulsed, like she had fallen in attractiveness by this revelation. Not that it mattered, my girlfriend and I aren’t in an open relationship or anything.
After some more dancing, my girlfriend came over and told me the ladyboys had invited us to go out dancing somewhere new with them. That seemed like way more fun than the sterile cabaret, so off we went.
We all walked off and the older ones, in their very manly voices and broken English, basically said they were too old for this shit and were going to sleep. They left promptly, leaving us with the young waitress. She told us to come with her and we walked to a main street to find a tuk-tuk. As we walked and talked with her, I noticed she had somehow exposed more of her cleavage. She was overall extremely attractive. It confused me. It gave me an erection.
I have no idea why this turned me on so much. I have never been attracted to anything but a woman, and here was this very feminine, very sexy person who was neither woman nor man but some new category (which also made me think my girlfriend had no need to be jealous). Being so confused about what was happening to me only seemed to turn me on even more.
We reached the main street and hailed a tuktuk. A tuktuk is basically a motorbike with a two-person seat attached to the back, so it normally seats just two. We got in with my girlfriend on the right, me in the middle, and the ladyboy - Katy - on my left. Since it was a pretty tight fit, I had my arms up on the seat back. i was touching my girlfriend on one side, but not touching Katy on the other.
It occurred to me that I should have put my arm around Katy as well, just for fun. But it was kind of too late. I tried inching forward, but felt a little silly. I stopped. I still wasn’t touching, but I was close. Then I came up with a trick that I thought was clever. I leaned forward to look at something on my right, so that my left shoulder naturally came forward. I very lightly pressed against Katy. I felt kind of childish and was going to go back when I felt a small push back against my shoulder… So soft and feminine and shy, it really turned me on. When I leaned back again, Katy came with me and snuggled discreetly. But only two seconds later, we arrived at the bar.
I had thought we were going to meet her friends somewhere, but it ended up being just the three of us. I felt a little awkward, but we ordered some vodka mixers and took a table. My girlfriend and I sat down but Katy obviously wanted to dance so we stood back up, near to the table.
Both my girlfriend and I were fascinated by Katy, and we asked her about herself after some drinks. She had been taking hormones since nine and had had breast implants. That meant she hadn’t gone through puberty. Does that make her a girl? A girl with a history different from other girls? I was still grappling with how sexy I found this non-woman.
Did she even have a penis? While my girlfriend was in the bathroom, I drunkenly asked Katy this directly. She blushed and said yes. I had expected that. But I was confused that it didn’t turn me off. I was still convinced that Katy was a she, a very sexy she, just a special she. But she wasn’t a girl, so my girlfriend didn’t need to be jealous. I drunkenly touched Katy’s lower back. It felt unsatisfying, and a little too muscular. There wasn’t enough of that girly softness which I love. Soon after, my gf returned.
After the first touch, I was continually turned on, fascinated and confused. I wanted to experience this Ladyboy. I felt like my girlfriend had no reason to be jealous, since Katy wasn’t a girl. But like I said we weren’t really in an Open relationship. Still, every time my gf went to the bathroom I got as close as I could with Katy. I became more and more forward. The first time, I had just touched her lower back. The second time, I grabbed and squeezed her ass, and caressed the space between her skirt and shirt. I never doubted that she wanted me to do this, I don’t know why. With a girl I would have been almost certain that I would be called out, and I would never have risked it. Maybe because of the tuk tuk incident, I felt confident that my desire was reciprocated and confidential.
Also during the second time, we ended up dancing back to back with her ass against mine. I couldn’t actually feel her ass, she was wearing some kind of Robin-Hood-Men-in-Tights underwear that gave away less than normal jeans do. No idea what that was all about.
The third time my girlfriend went to the bathroom, I was still erect from my confused but powerful attraction. I moved close towards Katy and rubbed my cock against her thigh while murmuring something bold and obscene. She asked me if I had a six pack and put her hand inside my shirt, then suddenly pushed me off of her. I shrugged to myself and kept dancing. Then suddenly, my girlfriend was at my side only twenty seconds after she had left. Shit! She had definitely seen me.
“You didn’t give me enough change for the toilet.” (The toilet was public and had an attendant that you had to pay each time, as is common in Thailand.) I gave her more change and she went. This time I only talked to Katy and kept a safe distance.
When my girlfriend returned, she acted completely normal. Okay, so she wasn’t jealous. I began to drunkenly imagine that she was as attracted to Katy as I was, and that there was a possibility that we may all end up in bed together that night. So I didn’t worry about it but I thought I would probably get in trouble later…
We continued drinking, me partly fuelled by my sexual confusion and desire. With some more time and alcohol, I became convinced that my girlfriend hasn’t seen anything. So, I became more reckless.
The next time my gf went to the bathroom, I again made advances on Katy. Fully erect from the excitement of sexual confusion, I pressed my cock firmly against her, moved close to her ear, and declared, “I want you.” She moved slightly back, creating a gap between us. But she wasn’t rejecting me. She slipped a hand between us and squeezed my shaft for a full second. She released it and moved closer to the tip for a second full squeeze while repeating the same words more emphatically, pausing after each: “I want you.” I was utterly turned on. It was the first time anyone but my gf has touched me in years.
Eventually, the party wound down and we had to leave. We grabbed a tuk-tuk and piled in as before. I was now fully drunk and fully aware that my ridiculous idea of a threesome was not going to happen, and my excessive drinking would probably also not be repeated in the near future. But I was still overwhelmed with curiosity about this Katy creature and this was my last chance.
As we sat in the tuk-tuk, I put my arm right around Katy’s waist and on her outer leg. I moved to hold her hand briefly, it felt large and veined and manly and I drunkenly released it and put the thought out of my mind. I went back to her smooth, soft leg and noticed that her pretty large purse was making a wall between my hand and my girlfriend’s eyes. What a coincidence. I unashamedly began stroking Katy’s inner thighs, they were smooth and soft and had strange grooves between the hamstrings and the quads. It was an extremely exciting exploration of new sexual territories that had never before been explored.
After exploring her legs, I began to wonder about the space between them. I tried to push her panties aside. But they were literally inflexible. I cupped, and felt a vague warmth and nothing more. I threw caution to the wind, I moved my hand to the waistline, I pushed inside, I reached in to feel the smooth skin in the No Man’s Zone, I pushed deeper in search of the truth, finally, I came to a small area of softer flesh…. It was completely unidentifiable. It was probably the base of a small penis that was folded down under the legs, but it felt vaginal. I was confused, not turned on. All of a sudden we arrived at Katy’s house, and she got out, said goodbye normally and went in. The tuktuk carried on to take me and my girlfriend home. I passed out almost instantly. My dreams of a ladyboy threesome remained a fantasy. Maybe it’s better than she was wearing those impenetrable panties.
My shemale encounters
I'm a married man in my mid forties. I have an older disabled wife. We don't have any children. We have been married for a decade. Ever since she was disabled, we stopped having sex. She gets depressed occasionally and has been taking happy pills for years. Maybe that's why she lost her sex drive and I don't blame her.
We never discussed about sex. I assume she minds me having sex outside (every woman does), but I still have needs. So I steal a little fun as and when I have the chance, with total discretion. I can sense that I get her green light as long as our marriage remains the same status.
I travel for work sometimes. This is when I get to satisfy my sexual needs. I will go for a body massage when I get a happy ending, hire an escort, find a sex date online etc. I also have a little fun when I travel back to Southeast Asia when I visit my family. Massage is a must have when we visit Bangkok.
One year, my dad passed away suddenly and I flew back alone to attend his funeral on the next available flight. It was long and miserable, both the flight and the extended funeral.
When it was over, I contacted a senior of mine whom I hadn't met for years. He told me that he was actually organizing a farewell trip to Bangkok for a uni friend who had cancer, final stage and asked me whether I would like to join them. I jumped at the chance and joined them in Bangkok for a few days.
They were a friendly bunch, some even brought their teenage daughters. There was lots of food, shopping and of course massages. In the end, I decided to stay a few extra days on my own. I chose a different hotel far from the red light district, closer to a local housing district. The next day, I wandered around exploring the area by foot. I came across a few massage parlors near my hotel. As I was getting a bit tired under the scorching hot sun of Bangkok, I decided to treat myself with a massage. I simply walked into a massage parlor and I was greeted with a Thai woman. I told her that I would like a body massage. She then sat me down and took off my shoes and offered me a cup of tea, as she took an album out asking me to choose my masseur. In that album, they were a mixture of men and women to choose from. I flipped through the whole album and decided on a woman in her late 30s.
After that, I was led to a room with a shower upstairs with a double bed. I was a bit surprised but didn't bother to ask why. I saw there was a shirt and shorts on the bed, so I just took off my shirt and trousers and put them on. A few minutes later, there was a knock on the door. I opened the door and there she was, my masseur in her skin-tight t-shirt and hotpants. She was quite petite, about 5'2" but busty. She greeted me the Thai way and I reciprocated.
"Hi, my name is Natalie." Quite a sultry voice.
"Hi, mine is James."
"You want to put on the shorts we provide?"
As she can see that I put on the shirt they provided but not the shorts. I was naked waist down.
"I can't, because they gave me two shirts."
She gazed at my penis and smiled, "maybe we should have the massage this way."
I smiled back.
"What kind of massage do you want?"
"I would like to try the herbal massage and then Thai massage."
She then closed the door, asking me to take off my shirt. I was a bit embarrassed because I was totally naked in front of her. She checked out my naked body with a sweet smile. As if she agreed with what she saw. I guess years of dieting and working hard at the gym finally paid off.
She placed her hand on my shoulder and asked me to lay on my stomach. Her hand was so soft and electrifying. I felt my heart skip a beat and my cock started to react. She then put a towel on buttocks, I was a little disappointed but didn't protest.
She placed a warm bag filled with herbs all over my back, legs etc. It was quite nice and relaxing. She then asked me to turn over. By then, I had a massive hard-on. As she held the towel when I turned over, she had a good look at my throbbing cock and gave me an even bigger smile. When she out the towel on my groin, it was like a tent...
She continued with the bag of herbs on my shoulders, chest. My sensitive nipples felt so warm when she put the bag of herbs gently on them. I can't control myself any longer and grabbed her hand. By then, she could sense that I was very excited and wanted something more. I placed her hand on my lips and kissed it gently...
She put another hand of hers on my chest and massaged it gently and lovingly. I kissed her hand even more deeply. She then put the bag of herbs away and dimmed the light as she took off her tight t-shirt, exposing her glorious breasts. I sat up with my huge hard-on, admiring her beauty. She then walked slowly to me between my thighs. I gently caressed her hair and held her face in my hands. I kissed her luscious lips. Once I started, I just couldn't stop kissing her deeper and deeper. She seemed to enjoy this attention and reciprocated. Her wet little tongue ran wild in my mouth. And so were my hands. I searched her breasts and squeezed them. When I touched her nipples, I was amazed how soft and big they were. I ran my lips down her neck and then her chest. I lowered my head so that I could suck her wonderful nipples. I had never kissed and sucked such heavenly nipples in my life! I had so much pleasure playing with them. So was her. She moaned and groaned as she wrapped her arms around my neck.
After seemed forever, she started kissing my nipples and sucked them gently which totally drove me crazy. She then did something which sent me straight to heaven by holding my cock in her mouth, sucking it greedily. She gave such a wonderful blowjob. I had to stop her before I shot in her mouth.
I placed her in bed and tried to take her hotpants off only to discover that she had a cock! A tiny brown cock. Then only I realized that my masseur was a ladyboy. I knew they existed and never bothered at all but I had never thought having sex with one. I was so horny then and I wasn't going to let this put me off. After all, I had nothing against the third sex.
"Is it ok?" Natalie asked.
"Not a problem."
"Have you fucked a ladyboy before?"
"Can't say I have. Maybe you can show me how. "
She sighed with relief and pressed her marvelous breasts against my chest, which was sensational. My cock was dripping hard with pre-cum and I was dying to cum. She applied some lube on my cock and her ass. She was on her back, legs in the air. She then guided me to the gate of heaven. It was so tight and warm. I inched inside her and she sighed of great pleasure. I had never had sex with a ladyboy in my life. From the fact that I had the greatest pleasure I had never had so far. I was glad that I finally discovered this hidden guilty pleasure. I fucked her as deep and I could and we both moaned and groaned like two wild animals. As I fucked her hard and furiously, she wrapped her legs around my waist and her hands played with my nipples. I had never experienced such intense sex and after a few minutes, I shot the biggest load of my life inside her. I was totally exhausted and rested on her for a few minutes.
When we recovered, we showered together and got dressed. I paid her handsome tips. We exchanged numbers and I promised to contact her next time.
How I became an escort; Cheryl’s story.
How did you start as one of the escorts?
I was studying English at the University, living on campus. My parents are not wealthy by any means so I had to fund my own lifestyle, which was tough. I got a part-time job at a local bar, waiting on tables. One of the regular customers who visited the bar was the owner of a local escort agency . One evening we got talking and to cut a long story short he dropped his business card on the bar and said if I ever wanted to make some real money to give him a call, so I did. Even though I knew it could involve having sex with clients I thought, what the fuck!
So you took the plunge and started working as one of the escorts?
Yeah, I was getting deeper in debt, my credit cards were maxed-out, I couldn’t keep asking my parents to bail me out. I always knew that men were interested in me sexually because I had loads of offers for dates with older guys in the bar, which I always turned down, and glad that I did because a couple of my regular clients at the massage parlor were guys that I remembered from the jobs that I had in certain bars.
Do you remember your first booking as a call girl?
Like it was yesterday. The guy that hired me had seen my pictures on my profile page on the escort agencies website. He liked young blonde escorts to accompany him to dinner functions. I knew that he wanted to fuck me from the minute we meet, which was good because I knew that he would leave the boring function straight after the dinner.
Did you have any sex with with your first client, if so, how far did you go?
Absolutely, he told me I was one of the most beautiful escorts that he had ever been with. After the dinner we went back to his hotel room and I got paid $500 for an evening of erotic sex, which lasted just for two hours. I actually got paid $500 for sex, in fact the sexual intercourse part only lasted about 4 minutes the rest was kissing, letting him fondle my breasts and sucking his cock for a while. It really was the easiest money I have ever made. I would recommend working for escort agencies as a first step for any girl that wants to start in the sex worker business.
How did you feel after the first time you had sex for money, did you feel as though you are now one of the prostitutes?
I was buzzing on the thought that I had become one of the call girls and that I could make so much money for having sex with men. Before, I would let guys fuck me for nothing. Fucking for money was empowering. I realised that working as female escorts in was something that I enjoyed. I no longer had to suffer the despair of having no money, no nice clothes and as an added bonus I discovered that having sex with lots of different strangers is quite a turn-on.
Do you still enjoy sex with the clients?
More than ever. I don’t think that an escort, a call girl, or the girls that work in massage parlors could do the job if they didn’t like to have sex with lots of men. In fact, I would go one step further; I get quite disappointed if a client doesn’t want to end the booking without wanting to fuck me.
What is the most requested service that clientswant sexually?
Nearly all guys want a real girlfriend experience with escorts. They want to feel that the girl they are with, even if she is twenty years younger than him, is receptive to his charms and that she does fancy him So, with the GFE service there is lots of kissing, oral sex and full intercourse.
As a call girl, how many clients do you usually see in a week?
Like most young female escorts I am always in demand, I limit my days now to four days a week and I only see five clients maximum a day. But I can make three to four thousand dollars a week in that time frame.
Do you ever regret leaving university for a career as an escort ?
I sometimes think about what I would have become had I graduated. But the truth is I love my life as a call girl. I’ve met loads of nice guys and also the other girls at my escort agency have become my best friends. When you’re in this business you tend to stick to other working girls who understand the nature of the job. I can’t imagine what my old friends at school would think of me if they knew the career path I had chosen, that I was now working as prostitutes do, only by another name.
Holly is a beautiful blonde escort , she started working as an escort while at University. Not only does Holly work as a call girl, she also broadcasts as an adult webcam model.
My Crossdressing Story
It was the late seventies and I was 16. I had to move towns to complete my university entrance years (11 and 12). My parents found me lodgings with a divorcee, a lady in her 40's living alone in a large house in an up-market suburb. She was very kind although a little highly strung at times, testament to difficult times prior to separation I think.
Anyway, it all started with a box of clothes which had been placed in the hallway downstairs, outside my room. I had noticed it over a number of days, including the folded tweed skirt suit on the top. For some reason, I developed the desire to try it on and so, one night, after my landlady had retired upstairs, I grabbed the box and took it into my room. Donning the outfit, I had erotic sensations which included an emission. I felt immediate guilt and returned everything to its proper place, vowing never to repeat this episode.
The next evening during mealtime, my landlady asked me if I had touched the items in the box. It was so sudden, so unexpected that I froze, unable to choke out a response. This I think was taken as a confession. She quickly changed the subject and we talked about other things.
The next evening, whilst watching television, she asked me straight out whether I liked 'pretty things'. I stammered out some sort of reply, a guarded affirmative but non-committal. After a pause she told me to follow her. We ascended the stairs and entered her room, which I had hitherto never frequented. Bidding me to sit beside her on the bed, she asked whether I had ever dressed as a girl. I answered that I had not. She asked whether I had ever wondered what it would be like. I simply nodded. Without further ado, she said she would like to give me that opportunity. Sensing my agreement, indeed probably my excitement, she told me to go *****, shower and return in a pair of silky pink panties which she now placed in my hand.
At 16 I had little body hair and was pretty smooth and slender. Once clean, I found that the panties fitted me perfectly, barring the tell-tale and increasing bulge at the front. I returned to her room and she immediately fitted me with a matching bra, assisting me with the hook and adjusting the straps to fit. She inserted 'chicken filets' to give me some shape (her daughter's she said - who was currently working as a Nanny in Belgium) then helped me put on some pantyhose. I shivered as she rolled them up, explaining to me the method I should use when doing so myself.
Soon a white, lacy fronted blouse was passed to me. I struggled initially - the buttons being reversed! Then, to my surprise, she produced the gray 3 piece skirt suit from downstairs. The below the knee skirt fitted snuggly, although she noted a little bit more hip and tush wouldn't go astray, an issue she would address a few weeks later via a padded panty. We both laughed, easing some of the building tension that had become apparent. The waistcoat was next and fitted nicely over the top of the belt of the skirt.
All the time she fiddled and adjusted to get the best fit possible.
At this point, she sat me down and applied a tiny bit of eyeliner, mascara, blusher and lippy. Nothing extravagant, but enough to give me a girlish, feminine look. Looking into the mirror, I was surprised by the effect but even more so when she produced a small 'Bob' type wig and brushed it into place. A watch, a bracelet, small clip-on earrings and a matching necklace completed things before I stood and she helped me into the jacket.
The reflection in the full length mirror by the wardrobe was stunning. I simply couldn't get my head around what I had been transformed into. She guessed my surprise and hugged me from behind. She said that I had turned out far beyond what she had anticipated!
She pondered on footwear for a moment. At this point, I came out of my shell and admitted that I had always fancied high heeled knee high boots. I never understood the attraction, but it was very real. She smiled and nodded, saying they would be perfect. From the wardrobe she produced her own black knee highs with the stiletto heel!! And what a great fit!
The boots, once zippered up snuggly about my calves, disappeared beneath the skirt (to this day I love that effect and believe that boots are far sexier with longer rather than shorter skirts). Initially, I tottered about awkwardly but then soon adapted to the need for smaller, shorter steps. I loved the smooth sway of the hips that heels invoked.
She took me by the hand and led me downstairs; fixed us both a wine and led me out onto the balcony overlooking the river valley. I felt so snug, warm and feminine dressed like this. I finally found myself chatting openly and honestly with my landlady, reveling in the situation. She too seemed happier than I had hitherto known her - perhaps it was the loneliness of the past few years, but she now treated me like kin, gently offering hints, bestowing flattering comments and encouraging me to 'be myself completely'.
This went on for the remainder of my boarding time with her.
When I got home from college each day she would have an outfit laid out upon the bed, not necessarily glamorous (although there were times she saw fit to do so) but feminine and comfortable. Dresses, skirts, polar necked tops, blouses, shoes with 1 or 2 inch heels were standard. Correctly matching underwear with nylons were insisted upon. Thus attired, I would complete my homework and study until called for dinner.
She tutored me in doing my own makeup, hair and nails. Moreover, she insisted that about the house I 'do it properly'. She took great pride in her second 'daughter', the one that her ex had nothing to do with!!!
We had many small adventures together; she concocting a number of scenarios with us posing as mother and daughter in public. Several of them could easily be written up as stories within themselves! (Let me know if anyone thinks it's worth it. I don't want to bore you all).
When I finally graduated/completed my studies, she made a huge fuss by purchasing a lovely evening gown with all the trimmings. She took me to dinner at the best restaurant in town, accompanied by her sister (who had become an enthusiastic and - in a sexual sense - active party to the arrangement, although my landlady never knew). Anyway, It was a lovely evening; laughs were had, tears were shed and profuse thanks passed either way.
I still think of her and miss her dearly. She opened a door to a place which has produced so many many pleasant memories and I am so grateful.