Desperate Ch. 05

'Such a pretty lady!' I mean, only a few weeks earlier I had been thrown-over by a no-hoper like Leroy. Now, a really attractive guy was schmoozing me. Me!

"Why thank you," I said with a smile. "I'm just here to listen to the music, maybe talk to some interesting people, have a relaxing time. The week's nearly over and I like to wind down for the weekend."

"Is your boyfriend meeting you here?"

"Oh, I - I don't have a boyfriend - er - right at the moment." I caught sight of Leroy's reflection again and I knew just what to say. "In fact, the last guy was a bit of a sleazeball. He had the nerve to dump me by email if you can believe that."

"Oh my God! What an asshole! And what sort of man would even dream of dumping a smart, elegant lady like you - let alone by email?"

All the flattery was going to my head. I had never in my life been described as pretty, smart or elegant. My insides were fluttering. Of course, despite enjoying the flattery, I wasn't so dumb that I hadn't guessed that Jake would probably be hoping that at some stage during the evening, he might have the opportunity to insert his dick into me somewhere. And the fact that not only didn't the thought of that worry me, but that it actually appealed - after all, you can't rape a woman who really wants it - made me feel horny all over again.

"Yeah, like I said, he's a real sleazeball. Not even good looking. I don't know why I had anything to do with him." I glanced at Leroy's reflection. Even though he was sitting beside me, he still hadn't worked out who I was, or that I was talking about him.

"Say, Tori. How about we move to one of the tables over there? The band's gonna start up in maybe ten minutes and I guess you may want to order some food. And it would be good if we can get to know each other a little better."

That evening with Jake was literally the most fun I've ever had - at least, with my clothes on. It seems he had his own electrical business. His main specialism was illuminated signs, but he also fitted-out shops, hotels and some upscale houses. In his spare time, he played guitar. He said he wasn't as good as the guys who played at the bar, but he was trying to improve by listening to the experts. I liked his smile, and I felt like he treated me like a princess. No-one had ever done that before.

I explained that I was the personal assistant to the CEO of a small company, and that my main hobbies were reading and going to the gym. He ordered a burger and fries, I ordered a grilled snapper filet and salad, with dressing on the side. The band were good, and we had a delightful evening; he seemed to be really interested in me, which no guy had ever been before. Afterwards, he offered to drive me home, and I accepted; I'd have five, maybe six Margaritas, and I was in no fit state to go anywhere on my own. He drove a BMW, which impressed me. When we got to my place, I got him to park around the corner.

I'd spent a lot of time during that evening, thinking about what I'd do if Jake wanted sex. The insane thing was that I wanted sex with Jake - he was handsome, considerate and really seemed interested in me - but I knew I needed to wait at least until Mr. Rogers had claimed my virginity, which I felt was rightfully his. When Jake turned off the ignition and leaned across to kiss me, I responded, and it was glorious. Here was a man giving me a hot, sexy kiss because he wanted to - because I was a hot chick! That just made me even more aware of how much I owed Mr. Rogers.

After a minute of kissing, in which I was a very active participant, Jake put his hand on my thigh. I felt a little qualm as it moved upward, but then I thought "Why not? I won't let him go all the way, but it will be good to see how he reacts when he finds I'm not wearing panties." When his hand reached my stocking top, he broke the kiss, and we both smiled. Then he slid his hand higher, and I felt his fingers touch the smooth and by-now very wet skin of my pussy, coming to rest against my slit.

"Hey Tori, why don't we go inside where we can have some fun. Looks like you came prepared for something hot. It must be cooler under that dress without the panties."

"Jake, sweetie, I - I make it a rule not to - not to fuck on the first date, or to bring anyone home. Now maybe on the second date..." I let the suggestion hang in the air, trying to sound confident but trembling inside.

"O - K," he said slowly. "So can I take you out somewhere tomorrow?"

I was glad he wasn't trying to insist; partly because I wanted to keep my virginity for Mr. Rogers, and partly because, if he did, I wanted it so much that I might just say yes.

"I'm a bit tied up for the next few days. Give me your number and I'll see if - when I can - er, open up a slot for you." I giggled. I was so nervous, and I'd made a very sexy suggestion to a man I'd only known for a few hours. A very good-looking, sexy man...

"Baby, you're such a tease. You've got me so horny." He stroked his fingers over my wet outer lips, and I let out a little gasp. "I can tell you're horny too. Your pussy is so wet baby!"

He was right - I was very wet, and getting desperate for some relief. "Look, Jake baby." I kissed him again. "I said that I don't fuck on the first date. That doesn't mean we can't still fool around a little."

A minute or two later I was lying on the back seat of his car, my skirt around my waist with one of Jake's thick fingers inside my cunt while he devoured big mouthfuls of my clit and pussy lips. Now remember that a few weeks before, I couldn't get a boyfriend. Now I was having some very wild sexual experiences with, in effect, a handsome stranger who wanted me! It didn't take very long for Jake to make me come, really strongly.

Jake shimmied up my body and kissed me, and I could taste my juices on his mouth. "Are you sure about this rule of yours? It would feel good for both of us if you broke it."

"Hey Jake, just - just show me - show me your cock, please." I don't know whether I was still trembling from the orgasm he'd just given me or the sheer thrill of what I was doing, how I was behaving, but it was so deliciously weird I felt like laughing. With some difficulty, Jake managed to shimmy around and unzip his pants. He went to pull them down but I just slipped my hand inside, groped inside his jockeys and pulled out a hard and rather intimidating cock. He was a little bigger than Mr. Rogers, maybe even bigger than Mr. Zucchini Senior, and for a moment I wasn't sure what to do. Then he bent forward, and it came close to my face. There was nothing else for it - I opened wide and swallowed his pride, just as I'd done for Mr. Rogers earlier.

Like I said, Jake was pretty big, so I couldn't give him the sort of treatment I'd provided for Mr. Rogers, but I did the best I could. Judging by the noises he made, and the thick wad of sticky fluid he deposited in my mouth after a couple of minutes, I'd say Jake was reasonably pleased with it. This time I was readier for the finale, and I was able to swallow it all without choking.

Jake was really sweet - sweet, that is, for a guy that had just deposited half a pint of cum down my throat. He helped me clean up, kissed me a lot and said some things that made me tingle almost as much as the memory of the pussy-feast he'd indulged in. "Wow, Tori, you are one hot babe. That was one of the best blowjobs I've ever had, and I love it that you swallow. I thought you looked real cute when you came into the bar, but I had no idea how sexy you could be. I'd love to take you on another date, if you'll let me. How soon could we do that, please?"

I smiled - I really couldn't say anything, as my jaw ached and my throat was sore. After a few moments I managed to gasp "phone number."

He pulled out a business card. "This is my cell. Call or message me any time."

I wiped my mouth and pussy with some tissues, adjusted my clothing so that my skirt was once again covering my thighs, and then he got out and opened the door for me, like a gentleman. It wasn't easy for me to stand up without giving him another look at my thighs and my pussy, but as he'd just been dining down there, that wasn't really an issue, as there was no-one else in the street. He hugged and kissed me so nicely. "Thanks for an amazing evening, Tori. You're an incredible lady. I'd love to get to know you better."

"Jake, you were amazing. I loved our evening together, and I'll let you know soon when we can get together. Goodnight."

"Goodnight, babe!" he called after me as I sashayed, rather unsteadily, around the corner and into my block. When the door of my apartment closed behind me, I kinda fell back against it and just laughed. I don't know whether I was just getting hysterical or if it was just from pure joy. A guy had picked me up in a bar because I looked real cute, we'd had a really nice time and then we'd made out in his car! We'd made each other come, and he wanted to see me again! Less than four weeks ago I'd been feeling almost suicidal because no guys ever seemed interested in me. Now I'd met a guy who wanted me - wanted to fuck me, at least - and I was still, technically, a virgin.

I realized that that condition needed to be remedied urgently, because I was now eager to put that particular hole to good, or possibly naughty, use, as soon as possible. The memory of Jake's big cock was intimidating and thrilling in equal measure, and once I'd showered, I went into my bedroom and employed my trusty vibrator to get me off again while I fantasized about what it would feel like to have Jake fucking me.

The next day, I was in the office extra early. I wanted to make sure that everything that I could deal with was done, so that as much of Mr Rogers' attention as possible could be paid to my pussy, as soon as possible. I also used the laptop to order a few more sex toys online. The son (and now grandson) of Mr. Zucchini were wearing out too soon, and I needed something more realistically-sized to prepare my vagina - sorry, my cunt, as I kept reminding myself - for what I knew Jake was going to put into it. And I was absolutely certain that soon - just as soon as Mr. Rogers had claimed his prize - Jake's cock would most certainly be filling my cunt. I could hardly wait.

Having arrived early, I left early on the Friday evening. I collected some large boxes from the 7-11 down the street from my apartment, and piled up some old newspapers and magazines. I poured myself a vodka and low-cal tonic - wine, I'd discovered, was too full of calories - and then cast a critical eye over my apartment. The place was stuffed with ornaments and memorabilia of my parents. I thought about the impression this would give to Jake, or indeed any other eligible man who crossed the threshold with the intention of getting between my legs. (And I hoped that there might be a long line of them, going around the block). Looking as objectively as I could, I realized that the apartment screamed 'sad old maid'. So I went around, picking up everything in turn. If I thought it was an old piece of crap with no real financial or emotional value, I dropped it straight in the trash; and there was quite a lot of that. If it was something that was too precious to throw out, but too embarrassing to have on display, I carefully wrapped it in newspaper and put it in one of the boxes. Soon, the apartment was looking a lot more minimalist.

Next, I looked at the décor, and I was not impressed. I measured up the drapes, which had hung in my parents' home, and looked through some color charts I'd picked up at the local Home Depot. Saturday was spent repainting three rooms. I went to the store around nine am, and bought all the equipment and the right amount of paint. I opened all the windows, and when I finally stopped at eleven thirty pm, the lounge had been repainted in an off-white, with a feature wall in a deep blue, and my bedroom had been re-done in a pastel lilac. On Sunday, I bought new drapes in fashionable matching shades, a new duvet cover and some better-quality sheets than I'd ever had before, and some new lampshades. I couldn't do anything about the carpets, but I hoovered them and added a cheap but stylish rug I'd found. It had a soft pile, and I imagined lying on it while Jake or Mr. Rogers fucked me. I poured another vodka and diet tonic, got out my vibrator, and came very quickly.

I hadn't forgotten to go the gym on Friday and Sunday - Saturday had been rather full on - and when I weighed and measured myself, I'd made more progress. Amazon deliver on Sundays, so my new plastic friend arrived in time for me to celebrate my new sexiness, lying on the rug with my legs wide apart, the big, cock-shaped vibrator inside me and the little one on my clit. I couldn't wait for my plastic friends to be replaced - or at least augmented - by something more flesh and blood.