Time and Companionship Only

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First meeting with a new Whore.
2.2k words
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Part 1 of the 2 part series

Updated 06/11/2023
Created 10/14/2022
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I like fucking whores.

To be clear, I mean women that get paid to spend time with me, fully aware that the main purpose of that time is to fuck. The disclaimer given is of course that 'money exchanged is for time and companionship only', but everyone knows that outside all the niceties, there will be intimacy, there will be fucking, there will be satisfaction for the punter and hopefully also for the whore.

It's an odd thing to admit, a preference for whores, escorts, courtesans, working girls. But the reality is that for some men, like me, the craziness of life doesn't allow time for intimacy. Stress makes it hard to cultivate a more meaningful relationship. Whores allow us to feel the moments of intimacy during and after fucking, the need for that closeness, and then leave without the additional burdens of managing a proper relationship.

Oddly, over the years, I have almost felt in quasi-relationships with a couple of whores. Not because of any love, affection, or naivity about the nature of our relationship, but because my interactions with them were reliable, regular, and familiar, all of which added something very pleasant to the transactional nature of our fucking.

By far my favourite whore is Rosie. We have fucked for nearly 10 years, gone through patches of me not seeing her for months, and then suddenly seeing her a few times in a week. We have had quick short fucks, overnight stays, even the odd trip somewhere. Over the last 10 years, Rosie has been the closest thing I have had to a girlfriend, we can chat easily, meet, fuck, and when we arrange to meet up it is like fuck buddies arranging a hook up.

Of course, one of the times I remember most was our first fuck. She was fairly new to the scene and her new page popped up in my search. She was surprisingly local, looked perfect as a ssbbw, and her profile made all the right noises about loving fucking. A text message enquiring for a short hook up netted a relatively quick response, and before I knew it I had a fuck lined up for my commute home.

Pulling up outside the address Rosie had given me, I found a quiet neighbourhood, and a nicely discrete side door to a house extension. Everything to suggest this was Rosie's actual home, with her using the extension for 'work'. I knocked on the door and it was opened with her stood behind the door in a towel. After walking in and getting 'paperwork' out of the way, she gave me a thorough kiss which left no doubt that this was going to be a serious fucking.

A large double bed was set up in the room, to which Rosie immediately went. As she walked over I had a chance to take in the creature in front of me. She had a huge ass which bulged out nicely, tapering in with her hips to curve beautifully up to her shoulders. Her legs were large, well shaped, showing some of the bulges you expect from someone very overweight, but also smooth and with great skin. As she turned around she had a beautiful face, no visible make up in the way of a huge smile, and huge soft breasts flopping down on to her stomach. Her stomach was prominent, so much so that she had a towel resting on it as if on a table. At 5'6 Rosie was easily 25stone if not more, a superb super sized bbw with big soft tits for playing, and for the next hour she was mine. Rosie took the towel of her stomach, laid down on the bed with her legs wide open, and called out, 'are you coming then?'

Snapped out of my inspection of so much woman, I couldn't get my trousers off quickly enough, decided there would be time to lose the rest of my clothes later, and lay between her legs for a deep french kiss. Rosie's hands were all over me until one had hold of my cock which started to receive some persistent attention, and her other hand held by head in place on her lips so that our tongues could wrestle together. During a seriously thorough tonguing, my own hand had an opportunity to feel and press against Rosie's skin. While she was big in every possible way, she was also very satisfyingly firm and it started to be obvious that she enjoyed being very firmly held and squeezed down. To test the theory I reached up and confidently took her hand off of my head and firmly held it down it on the mattress next to her head, which had the immediately response of her trying to get her entire tongue in to my mouth and some very slow but hard pumping of my now achingly hard cock.

The sudden and urgent horniness of our first two minutes on the bed was having an immediate reaction on my cock. As things stood, I could easily be just a minute away from shooting a load all over her stomach and leaving quite a mess. The situation was made even more emphatic by Rosie starting to run the head of my cock in to her belly, which was so soft it was like the most luxurious tit wank imaginable. I filed this sensation away as something to experiment with another time, as fucking a really big girl's belly button had always been a fantasy, but it was not one I wanted to use up now.

To prevent the inevitable storm of cum which was not far away, I took Rosie's hand off of my cock, and then moved my own hand to her pussy. It was no surprise to find an extremely wet pussy, two fingers slipped in with barely any pressure. What was a surprise was finding out tight the inside of her felt, and I quickly realised that Rosie was already close to orgasm herself with the muscles inside her pussy starting to contract. Without a moment's thought I took my other hand and pressed firmly against her clit, which generated an immediate response. The noise from Rosie's mouth was a deep and long 'oooooooooooooh' as she slowly pushed out all the air from her large lungs. Her pussy started to swell inside, it became so tight inside her that she almost forced my fingers back out but I stubbornly kept them in place to feel her contractions pulse around my fingers. Rosie put her feet flat on the bed, reflexively pushing herself upwards in to her orgasm, at the same time her free hand came around and clamped itself to the back of my head to bring me in to a hard kiss, and I could feel her holding her breath to ride out the wave moving through her pussy in to her body. After what seemed like an eternity, but was likely only about 20seconds, her ass suddenly landed back on the bed, my lips were released as she took a deep breath, and Rosie relaxed underneath me.

My experience commonly with women is that after an orgasm like this they can become very sensitive and want a few moments before being touched again. Rosie, however, was different. Her pussy started to relax, allowing my fingers to move again, and as I started to slowly bring them out of her she started to move against them again. Clearly, a girl as large and horny as Rosie needed a lot of fucking. So I pushed my fingers back in, which received another appreciative moan from Rosie, and brought my mouth down towards her pussy. I pushed my tongue firmly on to her clit and began a hard and slow up and down pressure from the tip of her clit down to where my fingers were rhythmically moving back and forth inside her pussy, simulating a slow and persistent fucking inside her. Rosie started to become vocal again, no words came out of her, but the deep 'ooooh' started to come every time she breathed out. Keeping the licking at the same firm but slow pace, I felt her build her orgasm inside, my fingers feeling her pussy start to close up again as if a vacuum was holding them in place. Again, Rosie held her breath and her pussy shoved itself up in to my face demanding that her clit be abused so that she could go over the edge, which she gleefully did with another long and deep sound as she found breath again.

This time, rather than give her a rest, I kept the same rhythmic tongue on her pussy and fingers steadily back and forth in her opening. It didn't take Rosie long to start another orgasm, a matter of a few seconds, and again my fingers were being squeezed together by her pussy. Rosie rolled through several orgasms this way over the next few minutes. I know that many women claim to wet the bed with their pussy juices when they orgasm, but this was a new level. Every time Rosie came, her pussy gushed around my fingers and a little leaked out every time, which combined with the saliva I was placing on her pussy was creating a very wet mattress under her ass. I was sure that if I wanted to I could start adding extra fingers and eventually get my hand in to this woman's pussy, I definitely wanted to know what she would feel like orgasming with my whole hand there to squeeze, but again I filed this away for another time. Now, it was my turn to cum.

Bringing my fingers out, I crawled up Rosie's body and finally paid some attention to her tits. They were large, which is expected with such a fat woman, very soft, and with large nipples that were rock hard. As my mouth wrapped itself around one of the nipples, I rubbed underneath with my tongue, and a soft breath came from Rosie's mouth. Her hands came back around and gently ran through my hair as I played with her nipple, occasionally letting my teeth graze them. My other hand had found the button on her other breast, where I was quite firmly rolling her nipple between my finger and thumb, pulling it upwards as if stretching them. Rosie seemed to respond forcefully to any squeeze on her nipple, the harder the squeeze the more she wanted.

The way her hips were starting to push against my pelvis I knew she wanted to be fucked and feel my own hips land against her. I brought my mouth off her tits and up to her mouth, which triggered her immediate reflex of lifting her legs up slightly to give me access to her pussy. With no effort at all, my cock landed slightly below her opening and slide upwards inside in one smooth and hard push. My body was so full of the feel and smell of Rosie I wanted to be absorbed in to her large firm body and rock on top of her for hours, but I was sure this would not last long. The experience had been so intense this far, I was not likely to hold out.

I again held one of her arms on the bed and immediately felt another gush of liquid in her pussy to show that she wanted to be fucked more. My head came down towards hers, letting my teeth roll along her shoulder, and whispered in to her ear that she should play with herself while being fucked. Her free hand immediately went to her clit and started to rub at herself with persistence and the noises coming from her throat made it clear she was close to another intense orgasm. Taking my cue from Rosie, I started to increase my rhythm, pushing myself in to her with greater force each time, my mouth found her nipples again and started to squeeze them between my tongue and lips, all of which lead to Rosie saying the first clear words since I had climbed on top of her. 'OH, FUCK ME!' burst out of her mouth as her orgasm began, the pressure around my cock became immense and Rosie frantically pulled me down on to her body demanding that I join her. Without any control I felt my cum shoot through my cock and fill the condom.

This however wasn't the immediate end, I couldn't stop fucking this woman. In part, because Rosie was still holding me in to her and bucking in orgasm and also because my own orgasm was continuing as I felt her contracting pussy on my over-sensitised cock. I quickly recognised that Rosie was going to cum again and furiously continued fucking her. I had never been a repeat cummer and knew I wouldn't be this time, but I wanted to see and feel this orgasm which was beginning before her previous one had even ended. 'SHIT, SHIT, SHIT, SHIT' came out of her mouth, her arms slammed around me, crushing me down in to her tits, her body arched up as if in spasm, and Rosie was holding her breath while I felt the muscles underneath her fat stomach vibrate every few seconds. Suddenly Rosie took a huge breath and her body collapsed down, I landed on her, still inside her, breathing hard and willing to rest.

After a while, a few minutes of small talk ensued.

After my shower I found a glass of water given to me, which was gratefully accepted.

Rosie was a fucking great whore, exactly my type, I knew I would see her again, and hopefully soon.

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