A True Whore’s Diary Ch. 01

Hi! I will return to the saga of Anne-Marie soon, but in the meantime I thought I'd share another diary entry from when I was 22 and working in a high class spanking brothel. At another time I'll maybe share an entry from when I was working in a sleazy massage parlour at 21 or when during the Covid lockdowns, I returned to whoring myself out by making private visits to clients. Would you like to hear about that as well? I am still nervous about sharing these entries as it is one thing having your writing and fantasies being slagged off, it's another thing when it is genuine bit of autobiography. I regularly re-read my diaries from when I was student sex worker and this day is one I often go back to. Please keep in mind that the following is transcribed from a diary entry so doesn't read like a traditional story.

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Very grumpy when Geraldine showed me the bookings for the day. Whilst I was delighted to be so busy, I immediately spotted I had Rosalind I. down for a two-hour session and Peter B. down for an hour. Geraldine told me it was my own fault for being the only girl currently on the books willing to be spanked by and service women. She also pointed out that being prepared to indulge someone with an extreme kink like Peter B. meant I'd have a regular client for years if I wanted them. Geraldine offered to take the 'bi' bit off of my biography of the website and not take bookings from Peter B. in future. However, I apologised and said: "I am only letting off steam. I just hate that Rosalind is so vicious and I hate having to woof and eat biscuits as doggy treats for that terrible man."

Geraldine did make me laugh when she said: "We charge Peter an extra £50 for you saying woof and eating biscuits. It's straightforward money. Claire did watersports for an extra £50 yesterday. You've got it easy!"

I asked: "Was she giving or taking?" Turned out she was taking and feel a bit ashamed to record that thought turned me on a little, though I can't work out if it was thought of me being degraded by being pissed on or the thought of someone degrading Claire by peeing on her.

This might be why I told Geraldine: "I'll take pee, but only for £100."

Typical of me. I start out by complaining about my most regular female client and I get turned on by the thought of another girl being degraded. I whine about being made to bark and I end up agreeing to try out yet another extreme customer kink.

My first client was Dr. A.. At least he was relatively normal! I enquired about why when he visits me he is always wearing formal grey-stripe wedding trousers. He told me: "They aren't wedding trousers. I am a Freemason. It's part of the attire we wear. Every time after I've seen you I go to Freemason's Hall for my lodge meeting."

I like Dr. A. as a client. He's very friendly, very straightforward about what he wants. When I asked him what he wanted he was very clear: "Schoolgirl anal, but with use of your other holes first. Can we do the first round fairly quickly? If so, I should be ready to bugger you before my hour is up."

He then chose headmaster role play with me in the blue uniform of navy skirt, pale blue cotton blouse, blue blazer, blue and gold tie, white socks, black flats, white cotton bra and knickers with lace trim. He was grinning when I came into the room so I must have looked more than OK for him. He's quite a tubby man in his late 50s with curly grey hair and never seems quite severe enough to be a proper headmaster. However, that doesn't stop him from giving a firm spanking.

The role play was based around me being caught kissing both girls and boys behind the bike-shed and putting my hands down their knickers and trousers. Under threat of my parents being told/expulsion I was quickly pulled over his knee. He used one hand to hold my wrists behind my back while my skirt was pulled up and I got a vigorous over the knickers spanking. He then began to feel my sex through my knickers and I started to get very wet. This led to him calling me a: "Dirty little girl. A filthy little slapper."

A good spanking and verbal abuse like that always arouses me, so by the time he pulled my knickers to one side they were soaked and I was so wet he was able to slide two fingers into me quite easily. I begged him: "Please Sir, punish me more. Please Sir, finger-fuck my dirty schoolgirl pussy."

This really got him going. My knickers were pulled down to my thighs and I got six, stinging blows before he began to finger-bang me again. I was thinking about how he had bought me to spank me and fuck me as a schoolgirl and I felt so dirty I started to get close to an orgasm. I was pushed over the edge when with two fingers thrust deep in me he said: "Your the naughtiest little girl I know. You love having an old man's hand in your cunt don't you?"

I wasn't able to give him a proper answer as I was spasming around his hand and crying out God knows what. After my orgasm had stopped, he made me lick his fingers clean of my oceanic taste and then he had me kneel and suck his cock. After a couple of minutes of kissing, licking and sucking his five-inch circumcised penis with his belly resting on my head, it was very obvious he wasn't going to last long so I asked looking up at him coyly: "Do you want to fuck my dirty schoolgirl pussy now Sir?"

He nodded and I put the condom on him with my mouth. He then took me roughly in missionary. He kept trying to kiss me and I resisted. I didn't want to break the role play and explain kissing was an extra, so I eventually gave in and gave it him for free. This made me feel dirty and aroused as I was a kissing whore. He only last about five minutes fucking me before he gave a big grunt and came.

After I had taken the condom off of him and clean him with wet wipes I asked: "What would Sir like to do now?"

"Bugger you senseless! But first you need to get Sir hard again."

"How would Sir like me to do that?"

"Play with your dirty little pussy."

So I did, lying on the bed, leg spread wide, rubbing my clit and sliding the 10-inch smooth white vibe in and out. I asked him: "Please Sir, tell me what a naughty, dirty girl I am. Tell me I am a dirty little schoolgirl whore."

And he did. For about 10-minutes till I had a lovely orgasm while he was name-calling me whilst I was fucking and spanking my clit.

The show did the trick and he was soon hard and taking my bottom. Not the roughest or most vigorous anal, though nicely dominant with him turning my hair into a ponytail to pull my head back whilst spanking me. Arousing, but I couldn't quite manage a third orgasm. He lasted about 10 minutes this time.

He gave me a £20 tip and told me he would see me the next time he came up to town for a Masons' meeting and would I be amenable to doing: "A naughty uncle and niece role play."

I said I'd be happy to try that. Didn't have the heart to tell him I have several clients already that have asked for it.

Take -- £160 + £20 tip.

My next client was Roger. C., another regular. I wasn't surprised when he selected exactly the same as he had last time. He wanted me tied to the bed posts by wrists and ankles in the starfish position, with me wearing white lace bra and panties, white lace suspender belt and white fishnet stockings with red patent leather heels and a black leather collar. He never says much during a session except to give orders and there's no role play element at all. All I have to do is lie back and take it and I think he quite likes me to be relatively passive. Geraldine would describe him as not much work. Then again she isn't the one being tied up and used by him.

Once I was tied up he began to roughly fondle my breasts through the bra and feel my sex through the panties. Occasionally he would slap my breasts or sex and then force his fingers into my mouth to be sucked. He then pulled my bra down and put his hands down my knickers and forcefully explored me. I was a little aroused and damp, but not much by my standards. He didn't have any problems being aroused and soon put on a condom. He then undid one of the ankle cuffs, pulled down my knickers so they were down by my feet on one leg and then re-did the ankle cuff. He then forced himself into me. It was a bit of struggle as he has quite a thick and long cock -- probably near to eight inches. He didn't last long and I didn't enjoy it too much as it was a little painful. However, I was a little turned on by it feeling degrading and totally beyond my control.

Once he came he gave me some really awful oral -- I hate feel stubble on my lips and he wasn't hitting my spots, just slobbering on me and trying to push his tongue in. Things got a little better when he used the 10-inch vibe on me, alternating between holding it on my clit or fucking me with it. A few minutes of this was getting me close and I began to urge him to fuck me harder, to rub my clit with his hand. He said: "Beg. Beg me for it bitch."

So I did. I can't remember exactly what I said, but I knew amongst the begging I uttered the phrases: "Please Master, bring me off. Please Master make your slut come."

I eventually got my reward and had a low-key orgasm. This turned Roger C. on enough to straddle me and begin slapping my breasts and pulling and twisting my nipples. He began to push my breasts together and spat on them again and again. This bit of degradation was the best bit of the session for me. Eventually he crushed my breast together and used them for a tit-wank until he grunted to a come that landed mainly on my throat.

Then as usual, he dressed and left without untying me. The couple of minutes between him doing that and Geraldine coming in to release me is always a bit unsettling, but also a bit of a turn on. I think it is a mix of the humiliation of him not even acknowledging me and the whole loss of control.

Take: £160.

After she undid me, Geraldine made us both a cuppa while I had a shower and then we sat down and had it and some chocolate digestives before my next client turned up at 1.

My third client of the day was a new one for me, though he said he had been to the brothel before. We had a good five-minute chat before we started He gave the name Teddy and as he was so fat my instant nickname for him in my head was Tubby Teddy (should have been Obese Teddy as he was at least five-six stone overweight for his height of about 5' 9"). It emerged that what he wanted really wasn't spanking -- though he might give me few little spanks during sex -- but for me to wear my hair in pigtails, wear white cotton socks with black strappy shoes, call him Daddy and protest while he fucked me roughly.

I told him I could manage all that and to: "Be as rough and selfish as you want, I get turned on by being bought and having no choice about what you do." That put a smile on his face.

When I came back into the room with my hair in pigtails and wearing nothing but just-below knee socks and the black, strappy court heels with the peep-toe, he was already naked and on the bed stroking his cock. His stomach was huge and their was a strong, nasty whiff of sweat. I got an overwhelming sense of revulsion, which of course, given my screwed-up wiring, turned me on. This hideously fat man had paid for me and was going to fuck me while I called him Daddy and my tummy was doing flips and my sex was wet.

He called me over and asked me to put a condom on him as he said: "I need to fuck your cunt soon." I rolled it onto him. He was only about six-inches, but he did have a big crown and was quite thick with at least two inches of girth.

He ordered me to lie on the bed on my back with my bum right on the edge of it. He got up and forcefully pulled my legs wide apart. He ran his cock up and down the length of my lips several times and rubbed my hood with the tip of it for a bit. I was protesting: "No Daddy, please don't Daddy", but I also let out a few genuine moans.

He grabbed my legs and took them over his shoulders and then gripped my hips, violently pushing into me with a big, somewhat painful thrust. His big belly flopped over me and the revulsion factor of that excited me as he began to give me a hard fucking. All the time I was coyly sucking my thumb and protesting and getting progressively aroused. After three or four minutes of that he leaned over and began kissing and slobbering on my neck and shoulders, completely trapping me under his bulk and I felt so disgusted that I had a big orgasm, gripping the bedspread and shouting out: "NO DADDY! NO!" as I came.

After a couple more minutes in that position he spun me round onto all four sand savagely pounded me. I rubbed and rolled my hood as he fucked me while holding onto the heels of my shoes. His belly was resting on my back and his balls were making an obscene sound as they slapped against my sex with his thrusts. He put his hands on the top of my bum and dug his thumbs into my hips and roared: "I'm going to come in your cunt!"

This pushed me over the edge and when I began to orgasm he put one hand on the back of my neck and screamed liked he was in a horror film and emptied himself into to the condom shrieking: "YOU CUNT!"

Even though he had nearly half an hour of his hour, left, he cleaned up and dressed and went without saying much more than: "I really enjoyed that." Despite him being so repulsive, so did I in my own strange way.

Take: £160.

As my next appointment wasn't until 2:30 Geraldine and I had lunch (sent out for noodles). When my fourth client arrived I realised the George P. in the appointment book was actually the man I nickname Grandpa George as he is way more than 70 and always wants granddaughter role play.

Today he wanted me to wear a flannelette pale blue and white pyjama top, white cotton knickers and nothing else. He said he would come into the room and punish me, finger me and then fuck me with some hair-pulling. He also said there would be gagging with knickers and asked if I had any: "Already soiled with vaginal secretions?"

Luckily I had the pair Dr. A. had made me soak and gave those to him. That seemed to arouse him more than a little -- even more so when he gave them a good, unsettling sniff. He asked if I would take a canning and I refused. I didn't like to say no, but I was very aware what Rosalind I. would want later and I couldn't face two consecutive thrashings with the cane. He was understanding, about the refusal, but I did say: "You can give me the hardest hand spanking I've ever had and make me think you are the meanest grandpa in the world though."

He went out onto the landing and when I'd dressed, came back in in full demon grandfather mode. He sat on the bed and pulled me across his lap. He made me smell my soiled knickers and said they were proof I'd either been masturbating or having sex with my lesbian friends. Either way grandpa needed to punish me. I gagged with the gag of my soiled knickers when he stuffed it into my mouth -- I had a left a very strong taste and smell on them.

Grandpa George then gave me an absolutely stinging over-knicker spanking for a few minutes, before pulling off the knickers I was wearing, finding them just a little damp and substituting them for the original gag. The bare bottom spanking came next and it was exceptionally painful. I needed that gag because I would have been screaming from the blows. I was genuinely sobbing with real tears down the face when he began to roughly finger-fuck me and subject me a tirade of verbal abuse. He had two fingers curled deep into me and his thumb rubing my bum hole when I came to him calling me: "A filthy lesbian scrubber. A dirty little whore of a granddaughter."

He kept fingering me for a couple of minutes after I had shuddered and clenched around his hand during orgasm and then he put a condom on and took me on all fours. Not as vigorous as the previous punter, but very deep due to large cock and he kept a good pace for more than 10 minutes. I rubbed myself while he fucked me, feeling very controlled and dirty with my wet knickers gagging me and him pulling on my hair to force my head back. All this made me have another smaller orgasm.

After he came and had gone flaccid and plopped out of me, he then became 'nice' grandfather, telling me what a good girl I had been and rubbing ointment into my burning red cheeks. He eventually removed the knicker gag from my mouth and I thanked him for punishing me like: "The dirty little whore I am."

Take: £160.

Very conflicted about my last clients of the day and I got very nervous and irritated waiting for Rosalind I. to turn up for her two-hour booking at 4pm. She is one of those rare clients -- I mean she would be rare just be being a woman client, I've only had two others -- in knowing that I am aroused by being bought, aroused by being a whore and having to do what I am paid for. Sessions with her would be brilliant if she wasn't such a sadist.

I had tummy-flips because I know she will physically hurt me and push me further than I want to go when it comes to the humiliation aspects of what she wants in her time. I sometimes want to protest about the inequality of her having to pay £50 and hour more to hire me as a woman, but then I remember she is physically repulsive and that she would cane me till I passed out if she could and don't feel like raising the point with her.

She turned up on the dot, dressed in a very expensive business suit/skirt -- Ridley I think -- and very nice jewellery. I still don't think any woman in their late 50s/early 60s should use L'Eau d'Issey as a perfume, but that is just me being bitchy. As is the fact, that she can spend a fortune on a look and it's still clear she has severe weight issues. I also don't get how she can have all that money and still wear her hair in the sort of Mary Quant cut that went out of fashion in the 1960s.

She said she wanted: "Schoolgirl vs. headmistress for the first hour with a cane thrashing and slave vs. mistress with a cane thrashing for the second."

I then did something I rarely do with regular clients and said no. I explained she was too rough, it wasn't fair on the client that came after her and it wasn't fair on me because she hurts me so badly I might not be able to work for a fortnight. She got into a right huff and said there was no point having a session at all if she couldn't give me proper thrashings. I held my ground and eventually she calmed down. She said: "You are lucky there aren't many lesbian spanking whores available otherwise I would go elsewhere."

I protested that I wasn't a lesbian and she said: "When I am paying you are whatever I want and you are a lesbian for the next two hours." That got me aroused and completely re-established her dominance.

She wanted me in the grey school uniform, plain cotton bra and knickers, but with a suspender belt and black, seamed-stockings. She had me put my hair in a pigtails tail and I wore black leather flats.

When I entered the room she was already behind the desk bending the senior cane. Her role-play spiel was that I had been caught cavorting in the back room of a pub with old men who were stuffing £10 notes into my stocking-tops, knickers and bra. She said: "You are a whore. You've brought the school into disrepute whoring yourself out to men like that in your school uniform. You'll have to be severely punished."

Even though I knew I was going to get a painful thrashing, I was a little bit aroused.

She very quickly had me over the desk for an over-skirt spanking, then an over-knicker spanking. Both were delivered with a lot more force than my male clients from earlier. Then she pulled my knickers down and made me count out two set of six spanks that were so hard I began to genuinely sob. All the way through this she called me: "A dirty little girl. A dirty little schoolgirl slut. A dirty little schoolgirl whore."

When her hand eventually went to my sex it was soaking and she then forcefully fingered me til I came powerfully while she shouted: "Take it, take it you dirty little lesbian whore."