Pretty Little Summer Dresses Ch. 02

Story Info
Bob gets a second date with Jess.
6k words
4.65
25.2k
21

Part 3 of the 11 part series

Updated 06/09/2023
Created 08/10/2018
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It was the weekend. Four days since my aborted date with Jess and I had been unable to think of little else. She hadn't been in contact again and when I checked my phone she had withheld her number, so I couldn't even call her. Every day since, I'd gone to that same coffee shop at the same time in the hope that she'd be there, but she never turned up.

When work was busy I often worked weekends, but business was slow at the moment. A number of my regular clients had gone bust, some owing me fairly substantial amounts of money; I really needed to either step up my game or consider seeking paid employment. I just hated the thought of not being my own boss; being at someone else's beck and call and having to do a regular nine-to-five.

I did myself some breakfast, nothing special - just a bacon sarny and then shaved and showered. I stayed in the shower a little longer than usual, letting the cool water spray over my body as I was thinking of my view up Jess's dress and what I had missed out on. I played with my cock a bit but the disappointment of what I had missed out on prevented a full erection and I gave up.

Once dried I put on a t-shirt and a pair of black jeans. I was at a loss as to what to do with myself; every time my mind was unoccupied it drifted to that evening in the wine bar and my missed opportunity. I had to find something to do.

I left my flat and walked towards town, not really knowing where I was heading. There were some pleasant distractions along the way; ladies wearing those dresses, causing Bob Junior to stir and I found myself following a couple of pairs of legs that were walking in unison. When I dragged my eyes away from the well-shaped calves and thighs, I managed to get a look at their profiles as they chatted to each other. The one on the left was younger, I'd say about early twenties, the other was probably twice that and I figured them to be mother and daughter out for a shopping trip. From the rear they both looked like they had trim figures and I started imagining them trying on outfits in a changing room; in my mind they were both wearing incredibly sexy lingerie which left little to the imagination.

I was surprised when they turned into the cinema entrance and I dithered briefly before deciding that a film would be a good way to get my mind off of Jess. I stood behind them in the queue looking at the films showing; it must be some sort of art week as none of the current blockbusters are showing and there are a number of films with foreign titles. I can't decide what to watch and listen to the older woman as she asks for two tickets for screen 4. Looking at the listings, I see this is a film called "Blue is the Warmest Color"; not knowing which screen I want I too decide to opt for screen 4. I get myself a large coke and follow the two sets of pins to the entrance; the younger woman smiles as she holds the door open for me and I take the opportunity to take in her figure, stunning! The two women, surprisingly, go to the back row up against the wall and I choose to sit about eight seats away on the aisle seat.

As the film starts I think "shit"; it's a foreign film with sub-titles. I hate sub-titles and I consider leaving. But the main actress is a pretty young thing that I've never heard of and I decide to stay to see how the plot develops. Wow, I'm watching a film about lesbians; two young lovers exploring each other's bodies and their sensuality. My hand is in my jeans caressing my cock when I suddenly wonder whether mother and daughter knew what they would be seeing. I look sideways to see their mouths glued together and the older woman's hand massaging the breasts of the younger woman. Hell, the action is hotter in the cinema that on the screen. I look around to see if anyone else is watching them and suddenly realise that, although the audience is sparse, from what I can make out there were just pairs of women - I seemed to be the only man. No wonder the counter lady had a bemused look on her face when I ordered my ticket.

Looking at the screen, the two lovers are in a bedroom scene; all hot young limbs entwined and mouths all over each other. Looking to my left I see a hand creeping up a thigh under the short hemline and, I can only imagine, playing with a steaming hot pussy. The two women are totally engrossed in each other and there is no-one else in the back row. I slowly unzip my flies and take out my cock, which I then proceed to stroke alternating between watching what is happening on the screen and what is happening eight seats away. As I turn my head back to the activity beside me, I notice the younger woman whisper something to her lover. The older woman turns her head and looks at me and then at my cock before returning her attention to her friend. The younger woman has now turned almost sideways in her seat and the "mother" gets to her knees and places her head between "daughters" parted thighs. Holy Cow, she is going to eat her pussy knowing I am watching. As I've been caught and there was no objection I decide to get a closer view and edge along so that I am just two seats away from them; the younger woman smiles at me as I do so before her face twists into one of absolute joy from the feeling of a tongue and several fingers on her snatch. I continue to stroke my cock vigorously, totally ignoring the film now; what I am seeing in real life is so much better. As the young woman nears orgasm, I reach the point of climax myself. With little option as to where to fire my load, I take the top off my half-drunk coke and fire several shots of cum into the dark brown liquid which forms a gooey white topping to the drink. I replace the lid, put the carton on the floor and tidy my cock away. As I get up, I smile at the young girl whose pussy is still being eaten.

Once outside the cinema I checked my watch, it was just after one and I decided to get some lunch. As usual I found myself constantly with views of those dresses, but they just kept bringing Jess back to my mind; it was like a constant reminder of my missed opportunity. I followed my latest pair of legs into "Lunchbox", ordered a chicken salad sandwich and sat at a table. As I was about to take my second bite my phone rang, I took it out of my pocket - number withheld - please let it be her I thought.

"Hello, Bob speaking," I said, instantly feeling like a fool; I never answer my phone like that.

"Hello Rob," came her sultry tones, "sorry I haven't been in touch, but Ashley only got out of hospital yesterday and I've been kinda busy."

"Not a problem Jess," I responded, "I've been very tied up with work myself," I lied.

"So," she began, "are you free for dinner tonight?"

"On one proviso," I replied, "you must promise me that you have no more friends that are going to get involved in car accidents."

She laughed. It was a sound that made my heart melt and my cock stir.

"I will ban all my friends from travelling in cars tonight if that's what you want," she answered.

"What I want isn't dinner; it's the dessert once we get back to my flat," I told her.

"Sounds cool," she said, "but I will need some protein inside me for the night I've got planned."

"Okay, when and where?" I asked.

"How about half seven at Geronimo's," she asked, "I've taken the liberty of already reserving a table."

My wallet jumped in my pocket; we had already been to the most expensive wine bar, now we were going to eat at one of the most expensive restaurants in town. Then I remembered the sight of her pussy under the table and my heart convinced me that it would be money well spent; well, either my heart or my cock, I'm not sure, probably the latter!

"Sounds good," I said, "I hear they do a good steak."

"They do a good everything," came back the voice of experience, "see you there."

I finished lunch in high spirits. She was still interested in me. I was still going to get my face and cock between those delectable thighs and sample the delights of heaven. God, it's been so long; my last fuck was with a prostitute on a drunken night about three months ago; I had been feeling down and given in to my carnal needs.

Leaving Lunchbox, I walked home with a permanent smile on my face. I reached my flat and showered for the second time that day; this time was different, I could manage an erection and my cum was flowing down the shower screen while I smiled at my memories of Jess's pussy.

Once out of the shower, I sat in my boxers watching afternoon TV and thinking about the evening ahead. Sure, the overdraft was going to take a hit, but that body was gonna be worth it. I alternated between recalling my view of her right tit and the view up her dress as I stroked Bob Junior through my underwear; before I knew it the inside of my boxers were covered in cum and I reclined on the sofa enjoying the feeling of the wetness in my groin.

I must have drifted off to sleep as I awoke with a start; it was six-thirty. I went to the bathroom to clean myself up; quick wash of the genitalia and a change of underwear.

Looking at my watch again, I think "Okay, plenty of time, Geronimo's is no more than ten minutes' walk away, now what to wear? Do I dress to impress or go casual like the youngsters of today? She knows I'm not a youngster, but she still wants to see me; dress your age, perhaps she's into older men." As the venue is Geronimo's I decided to wear a suit over a casual shirt, no tie. Looking at myself in the mirror I wasn't convinced, but I don't think I would have been no matter what I wore.

At seven fifteen I left my flat and walked the short distance to town. I entered Geronimo's rather furtively, feeling awkward and out of place. The maitre d' showed me to the table that Jess had reserved; it was secluded, and I started to feel at ease. I ordered a Scotch on the rocks without checking the price; big mistake I suddenly think. Shortly after my drink arrived so did Jess; she looked amazing in a knee length figure hugging sleeveless red dress. As she arrived at the table she bent down to give me a kiss and then took her seat opposite. She ordered a bottle of champagne (I broke into a sweat) and two glasses. When the bottle arrived and the glasses were poured she lifted hers up.

"Cheers," she said.

"What are we celebrating," I asked.

"We're celebrating Ashley being discharged from hospital and advance celebrating you bonking my brains out tonight," she answered, with a mischievous look in her eye.

"I'll certainly drink to that," I said, taking a deep swig of the champers.

We turned our attention to the menu and my heart skipped several beats. Jess saw the look on my face and laughed.

"No sweat," she said, "this is all going on my dad's account here. Order anything you like; in fact, order the most expensive of everything, he won't even check it."

I breathed a sigh of relief and looked at the menu with fresh eyes; this time concentrating on the food itself rather than looking for the cheapest options. I ordered a Porterhouse steak with fries and a side salad and Jess ordered a salmon pasta dish "plenty of protein" she said and winked. While we were waiting for the food to arrive, she was running her foot up and down my shin. She reached down and must have taken her shoe off as the next thing I knew her toes were getting friendly with my crutch. I reached down with my right hand and caressed her foot holding it against the growing bulge in my trousers. Her eyes were staring into mine as she took a sip from her glass and then licked her lips provocatively. Damn, I couldn't wait for this meal to be over and the real fun to start.

Between dinner and dessert, Jess excused herself and went to the ladies. My eyes were, once again, glued to her posterior as she glided across the floor looking like a mix between a gorgeous angel and the devil incarnate in that dress. When she returned, she walked up to me and dropped a red item into my lap; I knew instantly that this was her underwear and checked that no-one could see before I held them up to my nose and inhaled deeply; heavenly and slightly damp! I slipped them into my jacket pocket and occasionally would reach into it and feel them while Jess finished her cheesecake. This woman even ate sexually, and I swear she deliberately got some of the fresh cream on her lips so that she could reach up with a finger, collect the cream and poke it into her mouth. As she sucked the cream off her finger she looked into my eyes hungrily. My cock stirred as I thought of her taking my cream in her mouth.

After Jess had signed the bill to debit the cost to her father's account, we got up and left.

"I'm tempted to ask you to switch your phone off," I said, as we left the restaurant.

"I don't think we could be that unlucky," she responded, as she linked her arm with mine. "It's still bloody hot, even at this time of the evening. I can't wait to take some clothes off." With that she threw me a wicked grin.

"I'll be happy to help you with that," I offered.

She quickened her pace, "Come on let's get to your place. I wanna see what you've got hidden in your trousers."

As we entered my flat, I guided her to the living room while I went to the kitchen to get us a drink.

"Sorry," I called out, "I've only got Pinot Grigio in." I poured two glasses and turned towards the door.

"Fuck me," I said as I saw her standing in the doorway with her dress pooled around her feet. She still had her bra on but with her knickers in my jacket pocket she was, otherwise, naked.

"I was rather hoping it was going to be the other way round," she said with a smirk, "but if you've got a strap-on I'd be happy to oblige."

"Nooo", I said. As I took in the sight of her luscious body. Her pussy hair was merely a landing strip and she had a tattoo just above it. As I got closer I could see that it read "Cum into my parlour." I smiled at the invitation. "This way to the bedroom," I stated as I edged past her carrying the two glasses with me.

Once inside the bedroom I placed the glasses down and turned towards her. I took her in my arms and kissed her warmly on the lips; she opened her mouth and her tongue snaked out, seeking entry to my mouth. I opened up eagerly and her tongue was inside exploring my mouth and licking at my tongue. My hands dropped to her arse and I grabbed two lovely handfuls of soft, feminine flesh; I squeezed the mounds in my hands, revelling in how good she felt. I slowly released her cheeks and let my hands wander up to her bra; must be front-fastening I thought as I struggled to find a clasp. She seemed to be enjoying my struggles as I pulled away from her to get to the front of her bra, nothing! What the fuck, I thought. Jess laughed as she reached to a fastening at the goddamn side of the bra and whipped it off, her breasts were a sight to behold and my hands were soon helping themselves to the offering placed before me.

After allowing me a good fondle of her breasts, she pushed me back, up against the bed. She slipped my jacket off and then started on my shirt buttons, popping them open one at a time. She pulled the shirt tails out of my trousers, pulled it off and tossed it on the floor. Her hands were on my chest in an instant, seeking out my unimpressive pecs and playing with my nipples. She dropped her head and took them one at a time in her mouth bringing them to life like mini erections. She then reached down and undid the buckle of my belt, unfastened my trousers and unzipped my flies before letting my trousers slide to the ground. Her hand slipped inside my boxers, finding my erect penis which she extracted from my boxers. Her eyes widened as she viewed my cock in all its glory.

"That looks good enough to eat," she said, "but one thing at a time; I wanna feel that monster swimming inside me first."

She threw me back onto the bed and was astride me before I could catch my breath. With her smooth thighs either side of my waist, she slowly lowered her pussy onto my waiting member whilst staring into my eyes. I grabbed her waist as she slowly lowered herself, thinking what a lucky bastard I was. Recalling my last sex with the prossy I thought sure, the sex was good but there was something missing, call it a connection if you like and I hated feeling like I was on the bloody meter.

This was so much different. Jess, for whatever reason, wanted to be with me. Her eyes were shining with lust as she stared into mine, inching lower and lower onto my hard dick. The warm feeling of her pussy was making my nuts boil and I could almost feel my seed aching to explode into this lovely young woman's cock garage. I wanted to grab her, turn her over and take her roughly from behind but I could see she liked being in control and, hell, who was I to argue. I was about to get the fuck of my life and I was just gonna lie back and enjoy it.

When she bottomed out, a big smile spread across her face and she ground her pussy around in small circles, making almost purring sounds.

"I thought you'd have a big one," she said, "It feels so good inside me."

She began to lower her upper body towards me and I lifted my head and hungrily sucked on a nipple. She held my head to her breast as I coated her breast with my saliva whilst grabbing her butt with my free hand; kneading the soft, pliant flesh which, in turn, caused her pussy to move on my cock. She let out a low moan and then pushed me back on the bed as she started to ride me. She started slowly, all the time staring into my eyes.

"So, big boy," she said, "want is the age of the youngest woman you've ever fucked."

I looked at her, "Twenty- three?" I ventured, "Twenty-four?"

She laughed. "Not bad," she said. "I'll be twenty-three in two months. Now I want you to fuck the hell out of this twenty-two-year-old pussy. I want it red raw in the morning from the poundings you are going to give me, got that?"

I nodded eagerly and reached for her waist again as I sat myself up while keeping my cock in her heavenly hole. Now almost face to face I gently pushed her backwards so that she was lying on the bed and manoeuvred myself so that I was now on top of her. My cock slipped out, but I soon had it back inside her honey pot and slowly began to work it in and out of her, occasionally changing my angle of assault so that I was hitting different parts of her vagina. Her eyes never broke contact with mine; it was like she was trying to read me or to see through my eyes how much pleasure she was giving me. I could tell her if she wanted to know; the most pleasure I could ever remember having!

I began to increase the pace of my thrusts, causing her to grunt every time my balls slapped up against her perineum. My cock was slick with her juices as she became wetter and wetter, making it easier to thrust into her lovely tight pussy. I knew that as I hadn't had sex for so long there was no way I could make the first time last.

"I'm about to come," I told her, "where would you like it?"

"In my pussy," she responded, "I want to feel you explode inside me and then feel you leaking out."

I pumped harder and faster, but still trying to hold on to my load for as long as possible. Her gasps were adding to my excitement and I delivered a stream of my creamy goo into her honeypot. As I withdrew she said, "Bring that thing up here."

I did as she asked, and she opened her mouth and took my cock in, licking our combined juices off until it was clean.

"Now, lover boy, I want you to clean me up," she said.

I had never done anything like that before and my mind was in a state of flux. The thought of tasting my own cum did not appeal at all but I wanted to please Jess; I was in for a night of hot sex if I played my cards right and I couldn't afford to disappoint her. I put my head between her spread thighs and admired the view. Her pussy was as pretty as they come and normally it would give me tremendous pleasure to eat it out but I was about to swallow my own cum for the first time ever. I tentatively put my mouth up against her lips, which were coated in juices, and licked them. I was pleasantly surprised; not bad at all - no real taste just a thickish texture and slightly sticky. Having convinced myself that this was not going to be the awful experience I had dreaded I set about my task with renewed vigour. Lapping up the fluids coating the outside of Jess's snatch before probing my tongue into her where it met a large reservoir of cum. There was a distinct taste to her vagina, it was sweet, almost addictive and I would certainly be wanting to return to this honey pot again. My tongue worked away inside her, gathering all of the cum it could reach and I swallowed it manfully. When finished, I raised my head from between her thighs to see her beckoning me with her finger. As my face came close to hers she grabbed me and kissed me, forcing her tongue into my mouth and swirling it around.

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