Zeb’s First Time Experiences Ch. 02

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Anal

Just a recap to remind you of what happened in chapter one … I’m Zeb a nineteen year old architectural student. I have a girlfriend Ginny (Ginz) who is studying in another city. Ginny is both beautiful and smart … she also lost her legs years ago in a car accident and uses a wheelchair. I live alone but my life is far from dull. So far my first time sexual experiences have included a first blow job, first sex with Ginny, sex with another girl (with Ginny’s approval). I’ve also had a threesome and enjoyed anal. So let’s see what else I have to share in this chapter of my life.

Ginny had left to go back to college almost a week ago and I was curious as to how the seduction of her roommate, an Australian girl called Emma was progressing. Finally she called on Saturday evening and I could tell by the sound of her voice that something had happened.

“We did it, last night!” Ginny exclaimed!

“I take it things went well?”

“Oh you know just the run of the mill multi orgasmic experience … nothing out of the ordinary,” she replied trying to sound as though it was nothing special … but failing miserably.

“Way to go Ginz baby!”

“I know!” The elation was back in her voice. “It was so much better than I thought. All the tools of seduction Issy used on me I used on Emma and she responded just like I’d hoped. It was unbelievable!”

Ginny spent the next hour talking non-stop about her experience and I was so turned on by her intimate narrative that I masturbated the whole time. I could tell that Ginny had a hand down her pants as well … her speech highlighted at times by small moans of pleasure!

I felt no jealousy in regard to her liaison with Emma, just as Ginny hadn’t when I told her about Issy. Just knowing she was enjoying her sexual freedom made me happy and excited for her. We had already agreed that we were both free to explore new sexual experiences while apart

.

The next day I meet Issy for lunch … she’d also received a call to thank her for all the practical advice she’d given. We both laughed at how ecstatic Ginny had sounded at her newfound powers of seduction.

For the next two months life carried on as usual. Issy spent the night once a week and it always resulted in our sweat covered bodies gasping for air after a torrid session between the sheets. It never ceased to amaze me how Issy always introduced something new each time to spice things up … sometimes it was a new position or maybe a toy from her collection. On one occasion she turned up wearing a strap-on dildo under her clothes. It wasn’t until we were lying on the bed kissing that I felt a bump between us … I knew it wasn’t me as I was still soft and just starting to grow. Issy smiled as she saw the look of confusion on my face.

“Time for me to introduce you to my new friend,” she smirked. “I call him Rod!”

“And just exactly what do you think you’re going to do with your friend Rod?” I questioned in reply.

“Well he’s all new and shiny and has never been up a virgin ass before so maybe today is going to be his lucky day.” Issy pushed her hips into me so I could feel more of her rigid new friend.

“I don’t know about that.” My voice sounded a little unsure

.

“Come on Zeb baby, you’ve had my ass numerous times. I think you need to reciprocate and feel the pleasure it brings.” Her smile widened as she continued to rub against my groin.

“Pleasure to you or me?” I responded.

“Both baby,” she purred in my ear seductively. “I’ll be gentle with you … I promise.”

Issy stripped off my shorts, t-shirt and underwear. She then stood and did a slow strip tease finally revealing the five inch black dildo attached to her waist by thin leather straps. She played with the false cock, licking her hand and pretending to wank while moving her hips alluringly.

I have to admit by the time she approached the bed my cock was standing to full attention and I was ready for playtime!

Issy covered the dildo with lube that I kept in the bedside drawer and then used her fingers to grease up my butt hole. I was on my back with my legs up over her shoulders and she kept eye contact with me the whole time … a sly smile on her lips.

On a few occasions in the past I’d had a finger up my ass both by Issy and Ginny. But this was a whole different ballgame.

“Ready for Mr Rod?”

“Fuck! Lets do this!” I uttered and smiled.

Issy slowly pushed against my lubed hole and the dildo popped inside. To my surprise it didn’t feel too bad. Slowly the whole thing disappeared up my butt and after a few moments of discomfort it actually felt okay. Issy grabbed my cock and started to wank me as she began to fuck my ass. The sensation of movement on my prostate was strange but exciting and before long I was asking her to go faster with both hand and dildo.

“Fuck! I’m going to cum!” I announced as my hands gripped the sheets and my hips rose up off the bed.

I then had one of the most sensational orgasms I’d ever had, the feeling was amazing. Rope after rope ankara escort bayanlar of jizz shot from my cock in unison with Issy’s stokes against my prostate. I don’t think I’d spurted more than maybe five times before but at least eight jets of my sticky white liquid erupted out landing on Issy’s stomach and boobs

.

The surprising thing was I stayed rock hard afterwards and was able to satisfy Issy over the next half hour. I even strapped the dildo onto myself and double penetrated her. The dildo was definitely something we would both enjoy again!

I still had a lot of time on my hands during the week, I was cruising through the architectural course and had also finished the decoration of my new home. My prospective boss Doug wasn’t really allowed to give me work in the first year of my course … but he did come up with a solution to keep me occupied. He knew I liked photography, so I was presented with a top of the line digital camera and told to spend time photographing architectural styles around town. ‘Look, appreciate and learn’ were Doug’s words of encouragement as he sent me out on a mission of discovery. And discover I did … but it wasn’t quite what Doug or even I could have ever imagined!

I was down in the old town dock area early one morning snapping photos of porticos and façade’s from places built in the late eighteen hundreds. Mostly old bank and merchant buildings that had some stunning features and workmanship … styles that were literally forgotten in today’s modern glass and concrete structures. One façade in particular fascinated me … it was a smaller building only about twenty feet wide sandwiched between two larger buildings of the same era. The frontage was a pale yellow stone block with small weathered green double doors in front flanked by tall thin windows. The three story façade looked like it hadn’t been updated since it’s conception. The construction date of 1835 was engraved into the stone above the door, as was the original tenants occupation … ‘J. P. Small – Cobblers’. I suppose not a lot of room was needed for shoe making and repairs in those days. The second floor had an old hoist above wooden shutters that were once used for the access of supplies, the old-rusted wheel still hanging under the gantry. The shutters were now permanently open and revealed a large casement window. The third floor had a center window with an ornate wrought iron juliet balcony in front, probably fronting the old cobblers accommodations.

The building was now a small café. The only signage was a small board outside on the pavement proclaiming ‘Cobblers Café – best coffee in town’, written in a cursive old English style font. The sign must have had some truth to it as I had to wait numerous times for people to enter and exit between photos.

I was surprised when during a close up I spotted someone staring back at me from the third story window. I waved at the person but didn’t receive a reciprocating gesture … in fact I got a rather stern look back and then they flicked me the bird! I was a bit stunned and my overactive imagination flew to the conclusion that it was perhaps someone who was there for a forbidden liaison and they’d taken me for a private eye hired by their better half … well, maybe not! More likely simply someone who didn’t appreciate being in my photo.

I’d spent an hour outside taking pictures and making notes before deciding I was now obliged to at least buy a coffee to repay the owner for the use of their building in my research.

I entered to a rather busy café. Being so small there was only five tables to sit at and they were all occupied by a mixture of cliental … from business suits to dock workers. Old pictures of cobblers at work adorned the walls and wooden crates with old shoes and shoe making paraphernalia were dotted around in little nooks and crannies, the smell of fresh coffee beans hung in the air … it was a nice cosy set up.

I waited in line and ordered a flat white, the barista told me that there were tables upstairs and they’d bring my drink up to me.

I climbed the narrow wooden staircase and found myself in a large open room that covered the whole second floor. Rows of old shoes hung from the walls and I felt like I’d been transported back to a 1920’s shoe shop. I was the only person in the area and so I took a seat at the table in front of the open window. My coffee arrived a few minutes later and it lived up to the advertised signage … best I’d tasted in town. While enjoying my java I decided to take a look at some of the images I had captured. I was abruptly interrupted.

“We don’t care what they offer, we’re not selling. So you can fuck off back to your ivory tower and tell them that!”

I looked up shocked at the angry tirade, the girl had thrown at me . “I think you’ve got me confused with someone else!” I replied.

“Fuck off! I saw you. I know you’re planning what you’ll do with the site … taking pictures, making notes. We know there may be some … what do you call it ‘structural integrity’ ankara esmer escortlar problems … but we’re going to fix them ourselves so you can’t tear it down. So you can just piss off!”

The fiery young girl was wearing a loose fitting smock with paint all over it, and a very worn Yankee’s baseball cap. She stood with her hands on her hips … and if looks could kill I would be well and truly dead!

“I actually think this building probably has reasonably good structural integrity and why the hell would anyone want to tear it down?” I replied calmly trying to diffuse the situation

“What! Who the fuck are you?”

“Who the fuck are you?” I retorted.

“I’m Millie Drake and I own this place … well my sister does. Anyway aren’t you working for that bastard McMillian who wants to buy the whole block?”

“Case of mistaken identity I’m afraid. Names Zeb and I’m an architectural student who happens to think this building is magnificent.”

“Oh shit! Sorry, I just thought … fuck, I’m an idiot. I apologize.”

“I’d be upset if I knew someone wanted to tear this place down too … and apology accepted.” I smiled.

“Look let me get you another coffee to make it up to you.”

“Only if you join me Millie and tell me why you think this building might be structurally unsound? Maybe I can help.”

“Ah, okay.” Millie seemed a little taken aback by my offer. “I’ll be back in a minute.”

As she turned to walk away I noticed her long blonde hair pony tailed out the back of the cap, the last few inches were dyed a light blue color.

While Millie was away I took a quick look around the room at the beamed ceiling structure and the condition of the brick walls. There did seem to be some cracks and things but nothing was too out of whack.

Millie returned with two cups of fresh coffee … and a totally different look. Gone was the oversized paint stained smock and the cap. Her new appearance was stunning. Khaki shorts and a tight fitting black tank top revealed long tanned limbs and a nice, toned body, her waist length hair was loosely hanging around her shoulders. I couldn’t help but stare.

“What! Have I got paint on my face?” Millie asked in response to my fixated look.

“Ah, n ..no.” I stammered taking the cup from her outstretched hand. “You just look quite different from before.”

“What you prefer my tit’s in a tight top rather than my painting gear?” She asked with an impish grin.

I blushed at being caught staring.

“Hey just messing with you.” Millie continued smiling as she sat opposite. “Cute that you blushed though.” She giggled and sipped her coffee.

Now I really reddened up and could feel my cheeks start to burn.

“Sorry, I can be a little inappropriate at times. Warped sense of humor,” she said seeing my uncomfortable situation.

I smiled back and hoped my face was returning to normal color. There was a long pause as we both sipped from our cups.

“So you said you might be able to help. How?” She broke the awkward silence.

“Well first off, who and why does someone want to pull this place down?” I asked.

Millie related the story of her sister owning the building and the pressure that had been put on her to sell due to a consortium of investors wanting to renovate the whole street and install upscale apartments for cash rich city dwellers. The historic society had waded in and claimed that the buildings were of heritage value. The only way that they could now be renovated was if the façades were kept intact but the rest of the building could be gutted and rebuilt. The developers were now trying to prove that the structures behind were old and unsafe. They were hoping that most of the current owners couldn’t afford to do remedial work so would have to sell out. Millie’s sister Grace had received an estimate of seventy-five thousand dollars to fix things plus engineering and design costs but was struggling to find the money. The developers were trying to find more faults to make it even harder for her to afford the repairs.

“How much does she have? If you don’t mind me asking?” I queried.

“Grace has ten thousand cash, can get a donation from the historic society for another thirty thousand, plus the bank will lend her a maximum of twenty grand. So we’re fifteen short, and that’s only if there is no more hidden costs. I don’t even want to think about what an engineer and a designer would cost on top of that.

“Fifteen grand isn’t too much more to raise and I might be able to help out with the other areas.”

“We only have two weeks to confirm with the council that we’ve got it all covered!” Millie sighed. “To top it all off Grace has been ordered to bed rest for the remainder of her pregnancy due to high blood pressure. She’s not able to help at all and I’m in charge of the sinking ship.”

“I’m sure you could find someone to borrow the money from.” I encouraged.

“Grace won’t borrow another cent and she gets really upset when I even mention it. It took a lot of persuasion sincan grup yapan escortlar for her to even accept the money from the Historic Society guys. I think she’s given up on her dream of keeping the place … too much stress and she can’t handle it at the moment.”

“Okay, well like I said I think I can help with the design and engineering.”

“Wow. Thanks for the offer but I don’t really know you. Why would you help?”

“Call me a sucker for a tight black top.” I quipped.

It was now Millie’s turn to blush. I smiled.

“Actually I can talk to my boss about it. He would hate to see these buildings developed the wrong way, he’s got an architectural firm and loves this part of town. I’m sure he would want to know what’s happening here and I think he’d offer help.”

“I don’t know what to say. Thanks. But I still have to get fifteen grand, and it can’t be gifted or borrowed.”

“Any ideas?”

“Well I have a meeting in half an hour with a couple who want their wedding day recorded and I will make six grand from that.”

“Wow, six grand, you must be good. So what, you’re a café boss and a painter, plus moonlighting as a wedding photographer in the weekends?

“Actually I have a small production company. Just one employee at the moment, me! I work from upstairs. As for the painting I’m doing the walls upstairs to make it brighter. I normally don’t run the café, that’s Grace’s job I’m just helping in the crisis.

“Okay. Well at least you’ve got six grand toward that crisis … only a bit more to go.”

“My, my aren’t we Mr positive. It’s actually nine grand to go … a tad more than a bit!” Her tone was slightly cynical.

“Sorry, I didn’t mean to be flippant.” I apologized.

“No, I’m sorry. You’re only trying to help. I could actually be making ten grand from the wedding day if the photographer I use hadn’t up and left to work for a newspaper up north.” Millie lamented.

“Ten grand. What just for taping and photographing a wedding ceremony and reception?”

“Actually the fee is higher because they also want the wedding night taped!”

“You are joking! You mean they want you to tape them bonking?” I shook my head in amazement.

“Bonking! Who the hell uses that word anymore.” Millie laughed. “But yes, they want the bonking as well.”

“That’s kind of weird don’t you think … kinky?”

“They seem a nice couple. He’s a merchant banker and she’s a high school teacher. They’re older, in their forties and it’s the first marriage for both of them. I guess they are a bit kinky wanting that part of the day taped but hell it’s added a lot to my normal cost.”

“What you just set up the camera on a tripod or do you stay and move around doing close ups watching them do it all night?” I was intrigued at the thought.

“That’s what we are going to talk about at the meeting. But I have a feeling they might want to cancel now I don’t have someone to help with the photography at the ceremony and reception. Unless you want to help out, how good are you with that camera?”

“Not that good. I mean I’ve always had an eye for a good picture but posing people for family wedding shots, I don’t think so.”

“Let’s see.” Millie took my camera from the table and began scrolling through the pics I had taken over the last week.

“Not great eh.” I shrugged as she continued looking.

“Some of these are amazing!” She declared talking more to herself than me. “These shots of the girl with the tattoos are really good.”

I had forgotten I still had shots of Issy on there. I quickly tried to jog my memory regarding how revealing they were … she was nude in some but I don’t think any were what you’d class as pornographic.

“That’s a friend … her body is … quite unique.”

“Shit yeah. I’d love to know who her tat artist is, that’s really good work.” Millie looked up at me. “I’ve got a few tats myself … they’re kind’a hidden away,” she added with a smile.

I smiled back and sipped my coffee while she finished with the camera.

“You’re definitely good enough for the wedding and reception pics and I could do the family posing stuff. It would just mean snapping as many pics as you can and then I’ll edit them later. So what do you say? I could pay for your time.”

Millie sat staring at me waiting for my answer.

“Are you serious?”

“Yep. I mean you have an eye for it, I can tell. So are you in or out?”

“You do realize you only meet me less than fifteen minutes ago?”

“What can I say, I’m a good judge of character … and I’m desperate.”

I deliberated for a few moments as she stared at me with pleading eyes. “Okay, what the hell, I’m in. But you don’t need to pay me, put all the money into the building.”

“Excellent!” Millie held out her hand to shake. I smiled and shrugged before extending my own hand.

We then raised our cups and toasted the deal.

The kinky couple arrived ten minutes later and I was surprised to find they were reasonably normal. David was about six foot, slightly greying hair and looked fit and trim in a grey work suit. Kelly was a real looker … strawberry blonde hair, pretty face with deep emerald green eyes, she was a little overweight but her curves looked good in a thigh high blue dress. For a couple in their mid-forties they looked pretty good.

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