My Boyfriend Tells Me to Get Naked

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Girl meets man who help her with sexy fantasies.
15.4k words
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Author's Note

This story is a continuation of my story 'What would it be like', obviously it would be beneficial for you to read that story first but this story can also be read as a standalone story.

*****

I really love my boyfriend but he does get me to do the most embarrassing and humiliating things in public.

You see, shortly after I realised that I was really, really, totally, madly in love with him I promised him that I would always do whatever he asked me to do, and I'm one of those girls who always keeps a promise. I was, still am, so far into him that I would walk barefoot over red hot coals for him - if he told me to. He's a wonderful man who really looks after me, he buys me almost anything that I want, and some things that I would rather that he didn't buy for me, like see-through clothes, really, really short skirts and dresses and remote controlled vibrators that he can control from his mobile phone.

Maybe I should describe myself before I go any further. My name is Jenna and I am 20 years old, 4 foot 10 inches tall with long, blonde hair. I'm skinny and have a 32AA-23-30 figure with my little tits high up on my chest.

I met my boyfriend, Mason, just over a year ago.

Okay, my tits are small and I sometimes wish that they were bigger and Mason says that if I really want to get implants he will pay for them but he tells me that he likes them the way they are with their big nipples, that always seem to be hard, and small, dark areolas.

Mason says that he loves me the way that I am and doesn't want me to change any part of my body now that my labia minora have been reduced to nearly nothing. We both agreed that they were way too big and a couple of months ago he took me to a cosmetic surgeon to get them reduced to a nice, nearly non-existent size so that my pussy looks like just a slit until I open my legs. Mason says that I look about 10 years younger now that I've had that done. I was scared that it would hurt but it didn't, the worst part was the healing, we couldn't fuck for 2 whole weeks, but we've made up for it since.

So how does Mason embarrass me I hear you asking? Well it's in all sorts of ways. I suppose that it started when he started buying me very short skirts and dresses and asked me to wear them all the time. I haven't worn trousers or shorts since shortly after I met him. Knickers and bras were the next major thing to go. Although I always used to wear a thong, or go commando, having my pussy uncovered 24 x 7 was a big thing for me. It was shortly after I made the promise that he got me to stop wearing them all the time.

I hardly ever wore a bra because my little tits don't need any support. Mason says that that was one of the ways that he first noticed me, my hard nipples were poking at the front of my silk cami top that I was wearing to the pub with a couple of my girlfriends. Ella said that my poky nipples would get me laid that night, and they did, and Mason has been fucking me just about every day since that night.

I had to move out of my parents home when I got my first job in a different city and I was living in a little apartment with a couple of flat mates when I met Mason. It's a good job that I don't live at home anymore because my mum would go crazy if she saw what I was wearing, or not wearing, all the time these days.

The next thing that Mason got me to get rid of was my little landing strip. He prefers girls who are bald below the neck and I quickly promised to keep myself that way. He also paid for me to get rid of all my pubic hair permanently so that I never have to shave my pubic region again.

After all of the above, Mason's next thing that he told me to do was to stop crossing my legs when I sit down. Well this was a really big thing for me. It was bad enough wearing really short skirts without knickers but I could just about always manage to keep my modesty by crossing my legs and when Mason got me to stop doing that I really found it hard. My mother always drilled it in to me that a girl has to cross her legs when sitting and after going on for 10 years of doing it, it was really hard to break the habit. And that's even before I mention the embarrassment of my bare pussy being on display whenever I sit down. Okay it was usually just the front of my slit but I still shouldn't be displaying it for all the world to see.

When I asked Mason why he wanted my slit to be on display every time that I sit down he said that I have a beautiful pussy, one that I should be proud of, and that I should not be afraid or embarrassed to let the world see it. Well I like my pussy and I am proud that I have such a nice one, but to show it to the world every time that I sit down is something else, something that I'm still getting used to, and it doesn't help when someone stares at it or says something about it.

We go to the pub every Friday night with his mates and at first they stared at my slit a lot and the rest of my pussy when Mason told me to spread my legs so that they could get a better look. I'd soon got used to them staring at my nipples when I wore a tight top.

Then I had to get used to them staring at my tits that were only covered by see-through tops.

I remember one Friday night when they were staring at my bald pussy and I shuddered when I had a horrible thought that Mason might make me masturbate in front of them. Little did I know back then.

On another Friday night, when the pub was very busy and we were all stood in one corner, Mason told me to take my dress off and let his mates see me totally naked. Well, a promise has to be honoured, so I just did it. After about a minute of being totally naked I was happy when Mason told me to put my dress back on.

Having said all the above, yes it is embarrassing, and humiliating, but it does turn me on. I went from thinking about the embarrassment of them seeing my pussy to the embarrassment of them seeing my wet pussy and I was getting turned on thinking about Mason telling me to masturbate for his mates long before he actually did.

I remember the first time that Mason told me to masturbate for them and to actually cum for them while we were in the pub. At the time it was a wonderful feeling but straight afterwards I was soo humiliated that I just wanted to crawl into a corner and die.

One other thing that was been really hard for me to get used to is going to work dressed like I do now. You see I work in a large office and, although the only dress code that they have is that workers must be clean, body and clothes. Apparently, they brought that in when one of the girls there never washed and both her clothes and her body stank. Now I often get mistaken for a slut until I start talking then people soon realise that I just look like a slut.

When Mason left university he got a job in the city of London working in the financial markets and he made a shed load of money. The bad thing was that he had to work 16 hour days and most weekends. After 6 or 7 years he decided to go it alone as a money markets consultant. Now he works the hours and days that he wants.

After Mason and I had been an item for about 4 months he asked me to move in with him. He's 10 years older than me and lives in a big house all on his own. I'd been to his house quite a few times and observed that it was obvious that a woman had never lived with him.

The other big change around the same time was that Mason asked me if I wanted to quit my job and work for him. When I told him that I knew nothing about the money markets and hadn't even been to university, he told me that it didn't matter because all I would be doing was making the occasional cup of tea and keeping him happy.

I was a bit confused until he told me that employing me was a way for him to pay a lot less tax. I'd be his employee in name only. That sort of appealed to me and I left my job with the minimum of notice.

When I did move in Mason told me that it was pointless me wearing any clothes in his house and he told me to strip off every time that I arrived there. As there was only the 2 of us I was quite happy to go along with this. He'd seen me naked so many times that it just seemed natural.

What I hadn't thought about was all the delivery people, the gardener, the pool man and Mason's friends that pop round every few days. After running and hiding the first couple of times Mason told me to just act as if I had a burka on, which was easier said than done. It wasn't so bad with his mates because they'd seen my tits and pussy numerous times in the pub but it was the men that I'd never seen before that embarrassed me.

I mean opening the front door to a delivery guy whilst totally naked is so embarrassing. So is sunbathing naked by the pool when the gardener or pool man arrives to do their job. All Mason said when I mentioned that it was embarrassing was that it was no big deal and that I should be proud of my body.

Well I am proud of my body and I like the way that I look. What's more, I was starting to get aroused whenever men saw me naked which is also humiliating. Each time that it happens and I tell Mason he just grabs me and fucks me wherever we are at the time.

One time I was still lying on the sunbed by the pool with the pool man nearby. That was the first time that Mason fucked me with someone watching us and I have to admit that it was supper sexy. My orgasm was a really strong and loud one.

Afterwards Mason told me that he knew that I'd love the experience; and on reflection, I did.

After that Mason told me that if he wasn't there when the gardener or the pool man arrived I was to masturbate for them, either on a sunbed or in front of the nearest widow to them. I did / do, and yes it is a turn-on for me. I have great orgasms.

Mason has also got me to start taking tea and biscuits out to those men, naked of course, and I do it after they have watched me masturbate through a window.

The back yard is also overlooked by another house which has a couple of teenage boys living there. Their rooms are at the back of their house and I've spotted them watching me a few times. When I told Mason he just told me to ignore them, to imagine that his house was the only one for miles. Easier said than done and whenever I'm naked out the back I keep looking over towards their house. Mason's seen me doing this and he says that I want to see the teenagers watching me, that it will be a bit of a turn-on for me. He might just be right.

As well as Mason getting me to be naked at home all the time, he's started taking me out in his car without letting me put any clothes on. I was really scared the first few times and I nearly freaked out the first time we stopped at a stop light and a wagon pulled up alongside. The driver looked down and saw that I was naked and started taking photographs of me.

That gave Mason the idea of taking lots of photographs and videos of me while I was / am naked. I have to admit that I enjoyed modeling for him. It brought back memories of the time that I did some nude art modeling.

I enjoyed it right up until he said that he was going to put the photos and videos on the internet for the whole world to see. That almost freaked me out but at the same time I jumped on Mason and we fucked on the sunbed while the gardener watched, and I discovered that I like people watching me get fucked.

He did, and still does, put the photos and videos on the internet and he's shown me dozens of photos and videos of other girls doing similar things to what he makes me do so I'm no longer upset about him putting them there. In fact we sometimes watch similar videos so that Mason can get some fresh ideas as to what he can get me to do.

When he takes me out shopping or to dinner or to a pub I feel almost naked. He has me wear the shortest skirts and tops that are so thin that I can hardly feel them, and some of them are see-through so I really do feel like I'm walking around naked in public.

Where has Mason taken me when I'm totally naked? Well, the first few times were to the fast food restaurants drive-through. I was soo nervous when we pulled up alongside the little windows to pay or collect the food. The first window that we went to had a girl collecting the money and she stared passed Mason at me, but didn't say anything, not even a smile; but the next window had a young man and he really did stare at me. I was soo embarrassed.

After those first few times I had to get into Mason's car naked every time we went out. Thankfully, he lets me take a dress or skirt and top and I could put them on when we get to wherever, either when I got out of the car, if there was very few people about, or if it was a busy place, then I can put them on whilst still in the car.

This didn't always apply. You see Mason is into the outdoor life and early one Spring morning he told me to put on the hiking boots that he'd bought me and he drove us out onto the hills, to a very remote place with no sign of life anywhere. Then we set off on a hike up into the hills with me naked apart from my boots.

Mason promised me that we were going on a route that he's done before and never seen anyone else but I was as nervous as hell. We'd been walking for about an hour, and not seen another person, when all of a sudden there were 3 young men walking in the opposite direction. My heart started pounding and I begged Mason to give me his shirt but he wouldn't. He said that I was perfect the way that I was. Nice to hear, but it didn't help one little bit.

As the 3 young men got closer they realised what was walking towards them and out came their phones. I have no idea how many photos or videos they took of me before we actually reached them. When we got within hearing distance Mason said 'good morning' to them and they said the same back.

Then Mason stopped and asked them what the weather was like on the top of the hill that they'd just come down from. I had no choice other than to just stand there and let them stare at my naked body. I could have put my hands in the strategic places but Mason had already told me not to.

The thing was, whilst we were all stood there I felt my pussy get wet and by the time we parted, I could feel my juices leaking out of me. I was soo pleased that I could keep my legs together. The strange thing was that none of the 3 young men asked why I was naked.

When we were out of hearing distance I told Mason about my pussy and he stopped and put 2 fingers in me. When he pulled them out he held them in front of my face and said,

"So you are, open wide."

I opened my mouth and he put his finger in for me to taste myself and lick his fingers dry.

When we got to the top of the hill we had a short rest, well short enough for Mason to fuck me. Thankfully with no one else there to witness our copulation.

The hike back to the car was peaceful and I slowly realised that I liked naked hiking, just so long as we were on our own. Unfortunately, we weren't on our own when we got back to the car. There were 2 other cars there with people getting ready to go, of having finished, hiking. I wanted to hang back and hide until they'd gone but Mason took my hand and led me back to the car with all of the people watching me.

Mason has taken me on 3 more naked hikes since that first one, and on each one there are more and more people walking the same route as us. All in all I must have been seen naked by 30 + people, none of whom had anything derogatory to say about me being naked and I have had quite a few complimentary comments.

Mason always finds some place that he can fuck me out in the open and on 2 occasions we had an audience - of sheep.

Hiking isn't the only sporting activity that Mason likes. When the weather isn't good he takes me to a leisure centre in a nearby city to swim, play squash or badminton. He has bought me a bikini for when he takes me swimming. The bikini is made of very soft, thin, unlined, mesh material that is see-through. It clings to my body and you can easily see every little bulge and crevice, Mason loves my camel toe. The bikini is yellow so that at a distance you can't tell that it's see-through, which I like, but close up, and when it's wet, I may as well be naked.

Yes I know that Mason has a pool and that I swim naked there but he likes to take me somewhere where I can be seen by lots of people. The changing rooms at the pool he takes me to are unisex with lots of cubicles and Mason always leaves the door to the cubicle open so that anyone passing by can see me changing; and he insists that I stand around totally naked while I sort everything out.

The pool has slides and a wave machine and we have great fun. Mason keeps me busy so that I don't have time to get self-conscious or embarrassed but I have noticed people looking at me, especially as Mason doesn't fasten the strings tightly and it's not uncommon for the water to push the material to one side, uncovering one of my tits or my pussy lips. Mason usually takes me at a busy time so that the staff have a lot more to do than look at swimsuits to see if they are see-through or not covering what they should cover.

The showers at the pool are mixed as well but everyone wears their swimming costume to get showered. Because my bikini is see-through when close up or wet, I often have men showering near me and looking at me.

I'm starting to realise that I like that and I've often pleaded with Mason to fuck me when we've got back to our cubicle, even though he leaves the door open.

For the badminton and squash Mason has me wear a T-shirt tank top that is long enough to wear as a dress. Well Mason says that it is but I don't like it because it only just covers my butt and pussy - when I'm stood still. Of course both those games involve moving about a lot and both my butt and pussy are on full display quite a lot when we're playing.

The squash courts have a glass wall at the back with tiered rows of seats for people to watch the games and I'm sure that I must be giving the audience a great view of my butt and pussy, but Mason keeps things moving fast and I don't get much time to think about what I'm showing.

The badminton courts are in a big hall and the 4 courts are's usually occupied. There's seats all around the sides of the hall and there is usually a few people sat on them and the people near where we are playing get a great view as I always seem to have to reach up to get the high shots.

We usually have to wait for a court to become free and we spend that time in the little cafe. Mason has me sit the same as I always have to and I've lost count of the number of times that I've blushed when I've caught the eye of someone looking at my exposed pussy.

One Saturday a couple of months ago Mason took me to a football game. It was an away game and we went there by train. As usual, Mason told me to wear just a very short dress so I was pleased that it was an unusually warm day for the time of the year. Apart from all the comments about my legs and bulging nipples all the time, the train journey back was really embarrassing. Well it was when I woke up, you see I was sat next to the window with Mason sat opposite me, and there was no table for that group of 4 seats.

I was happy that Mason was opposite me because it meant that he was the only one who could see up my dress when I was just sat there, legs not crossed as normal. I even sat perched on the front of the seat with my knees apart just to tease Mason, but that backfired on me when he lifted my window side leg up and rested my foot on his leg.

That wasn't the problem, what was the problem was that I got bored and fell asleep. Mason realised that I was asleep and lifted my leg so that my foot was flat on his knee and my knee was up in the air. This meant that my dress was pushed up and all of my pussy was on display to the man sat next to Mason, and anyone walking down the aisle, and once 1 football fan knew, all of them knew, and lots of them walked up and down the aisle to see the pussy belonging to the sleeping girl.