Losing my Sugar Baby virginity

It’s early August and I’m heading up to the big city of Truro to meet Hugo; my first ever paying customer. I’m wearing a short flowery summer dress with wedged heels, over my newest black panties and bra. I’m wearing what I’ve been told to wear and have already sent Hugo a photograph of myself in both my dress and my underwear for his approval. In return I’ve received a very dashing picture of him wearing a cravat and wide brimmed hat. It’s the first time I see his face, as the picture on his profile only shows his body; he’s got a handsome face though and is the very essence of an eccentric English gentleman. 

I could tell by his online profile that he’s a wealthy man, and his photo confirms it (only wealthy men or artists can get away with wearing a cravat). In his profile picture on the sugar daddy website, he’s wearing a very expensive looking suit, in what looks like a rather lavish house. Now, I’m not an expert on men’s clothing, but even I can tell the difference between a well-tailored suit and a cheap one; this guy is the real deal. 

I’ve arrived early and I’m feeling nervous; quietly asking myself why I’m doing this, why I’m parked in a supermarket carpark waiting to be picked up to have sex with a man I’ve never met before. This isn’t the first time in my life that I’ve questioned my actions, but this is probably one of the riskiest things I’ve ever done. As something to do, and to calm my nerves, I go into the shop to use their facilities and buy a drink; I’m worried that if I don’t, I’ll get a ticket for leaving my car there. Honestly, of all the things to worry about in that moment, it’s not whether this guy is going to be a crazy axe murderer, but whether I’m going to get a parking ticket, funny how the mind works… You may be thinking at this point (and rightfully so) that I’m either crazy or stupid (or perhaps both), and maybe I am; although in my defence, everything happened so quickly, he only messaged me yesterday, so I hadn’t really had time to think about it. Maybe if I had, I’d have decided against it, and I’d be relaxing in the garden with a nice cup of tea instead of waiting nervously in a supermarket carpark to be collected like some click and collect weekly shop. I’m impulsive and a risk taker though, bordering on irresponsible, so here I am, ready for collection.  

Hugo has come down to Cornwall on business, just a flying visit. He’s not staying the night, so going to take me (literally ‘take me’) outside somewhere. I have a picnic blanket in the back of the car, which he asked me to bring. I was so flustered when I left my house that I actually forgot, but thankfully my car is such a shithole that I had one in the boot anyway, along with buckets and spades, and a load of other crap. 

He’s told me what he’ll be driving and that he’ll be pulling a trailer; I anxiously watch every vehicle that drives into the carpark. Thankfully I’m not waiting long before I spot him pull in; taking a deep breath I get out of the car, grabbing my handbag and the blanket. A tall handsome man wearing mustard yellow trousers (another wealthy man wardrobe essential), and a striped shirt is walking towards me, holding out his hand to take mine. He tells me how beautiful I look, whilst he leads me over to his Range Rover. I ask what’s in the trailer, he opens a door to show me a very impressive and expensive looking vintage car.  

I climb into the passenger’s seat (and I mean climb, it’s a big vehicle), and he shuts the door behind me. I am now his; I have committed myself to him; the time to back out has passed. I feel butterflies in my stomach, although I’m not sure whether it’s because I’m nervous or excited. As Hugo walks around the car, I watch a family opposite us wheeling a cart full of shopping, thinking to myself, yes… whilst you go about your ordinary humdrum lives, I’m here being picked up to have sex for money. The thought excites me, and I feel a tingle between my legs. I’ve somehow slipped into some parallel universe, gone through the looking glass; and there’s no going back. 

As evident from his messages, Hugo is well educated and well spoken, the stereotypical public-school boy. I can imagine him at Oxford or Eten, fucking a pig or whatever they do to entertain themselves there. I tell him a bit about myself (not that there’s much to tell), and in return he tells me more about himself. He’s 59 years old, he’s married, and has two grown up children. The fact that he’s married does not bother me, and I’m quick to reassure him of this; not that he’s worried obviously, he probably does this all the time. He lives somewhere on the outskirts of London, but travels all over the world for work. He’s a dealer of expensive things: vintage cars, antiques, jewellery, anything really that is worth his time. I say ‘work’, because in reality, he’s probably inherited a lot of his wealth, and does this because he can, and it gives him something to do. Today he’s driven down to Cornwall to sell the vintage car in the trailer and is driving to Switzerland tomorrow to pick up another one. My mind boggles at how someone can talk so casually about driving there and back in a day just to pick something up, it’s a lot for a country girl like me who barely leaves Cornwall, let alone the country. He explains how he will take the car out of the trailer a couple of miles from the border, drive it over, and then go back for the other vehicle in order to avoid paying export tax. As I listen, I’m reminded as to how rich people stay rich by avoiding such costs.  

His hand is resting on my thigh as he talks and he’s admiring my long legs. He’s not entirely sure where he’s going, but heads out of town and down a maze of country lanes, until eventually he finds a large gateway big enough to park in. I think about how inconsiderate it is to block the farmer’s gateway (typical farmer’s daughter), and just hope that they don’t need access to their fields in the next hour or so; I don’t say anything to Hugo though. We climb the gate and head across the field till we reach a secluded spot. We are clearly trespassing on private property, another fact that doesn’t bother Hugo, and another observation I keep to myself. If we get caught, he can do the talking; he’s in charge. As we cross the field, he hands me an envelope, which I clumsily stuff into my handbag.  

The countryside is beautiful, and we find a spot looking out over the valley, towards a patchwork quilt of green and yellow fields; it’s the perfect setting. I spread the blanket on the grass and lay down in the sun. For a while he just sits there admiring me, before passionately kissing me and telling me again how beautiful I am. I remove my dress and underwear, feeling the heat from the sun warming my skin. His hands start to explore my body and I close my eyes, more than happy to let him touch and caress every inch of my naked flesh. Once he’s finished exploring my body, he stands over me, and carefully removes his clothes. He kneels on the blanket, and I take his cock in my mouth. He is dominant and takes control, telling me exactly what he wants. He has sensitive nipples and wants me to squeeze and twist them, he groans with pleasure, and I feel his cock throbbing in my mouth. When this becomes too much, he turns me around and takes me on all fours. After fucking my pussy for a while, he withdraws and repositions to take me up the ass, lubing me with saliva and priming my asshole with his fingers, before entering with his cock. I’m a little taken back, but I don’t fight it, I just relax and let him enter me. Thankfully I’m no stranger to anal, but I’m still surprised at how easily it happens, it’s not normally a first date thing for me, but then I guess this isn’t a normal first date. After a while he turns me over and climbs on top of me. He enters me from the front this time, which is how he finishes, coming deep inside me, kissing me as he does so. 

We lie in the sun for a while, composing ourselves before we dress and head back to the car. Thankfully there’s not a farmer in sight, we have gone unobserved. During the drive back Hugo takes a few work calls; one from the guy who’s buying the car. I can sense that his mind is on what needs to be done next; it’s back to business, and chasing money, playtime is over and very soon I will be but a distant memory. 

When I eventually get back to my car, I tear open the envelope to see how much money he has given me; how much my body is worth so to speak. We never agreed a fee before meeting (rookie error), although I wouldn’t have had a clue what to charge him anyway, so maybe that was just as well. The arrangement was that he would give me a ‘nice envelope’, and make sure that it was well worth my time; and apparently that was all the encouragement I needed… 

I take out a handful of crisp £50 notes, they look pristine and freshly pressed. I hold them up to my face and take a deep breath, they smell good! I count them out before carefully placing them back into the envelope and tucking the envelope safely into my bag. 

I feel adventurous and sexy, and like I can accomplish anything I set my mind to. I may be going back to dishes and dirty laundry, but I don’t care. As I tackle my housework I relive my eventful afternoon, smiling to myself at my naughty secret. My life has been changed forever, no longer normal and boring but full of excitement, danger and possibility; I feel alive for the first time in a while. 

It’s not the last time I see Hugo, although I have to wait quite a few months before I see him again, by which time I’ve seen several men and am a seasoned pro (in every sense). I haven’t seen or heard from Hugo recently, and the unfortunate truth is that I don’t know whether I will ever see him again; I don’t even know whether he’s still alive. Whatever the future holds though, he’ll always be special to me, having been my first; and I will never forget that beautiful sunny day lying naked next to him in a field in the middle of nowhere. 

Emily-Rose xxx