Don’t Poke The Bear

Chapter 19 Jack Owen

POV Jack Owen

We lay there passionately kissing for while and it was loving and tender. In the past she had ran out of the coffee shop so many times for her family and here she was in my arms without a care in the world and I must admit I liked this new side of her. I had admired how mothering she had been to her whole family but part of the reason I didn’t want to be with her before was because I never thought she would ever be able to put me first but now she had told me that she wanted to be there with me, I could really see a future for us and it was the happiest I’d been in years.

We spent the next four weeks together in my hotel in New York. Everyday with her was an adventure. I had never known anybody so care free and uninhabited. We ate in gorgeous restaurants and f****d in the bathrooms. We danced in dance clubs and she would rub up against me and kiss me like nobody else was there. We sat close together in a jazz club and she would wank me under the table. We went to the opera and she sucked my c**k in the taxi on the way back to our hotel suite. I had spent a lot of time in New York before but she showed me another side to the city. We went to dive bars , speakeasy’s and baseball games. We stood at the top of the Empire State Building surrounded by tourists as she pulled her coat around us both to cover us as she played with my d**k until I came in her hand. There were days we stayed in our suite and made love for hours. I tried to take her shopping but she didn’t want anything from me. I knew she wasn’t a gold digger and it was a breath of fresh air compared to my past relationships, until I took her to a lingerie store and I spent an absolute fortune on sexy underwear for her. She said she only let me pay because the underwear was really for my own benefit. One night I was completely exhausted and I asked if she wouldn’t mind making me some of her delicious food because our suite had a small kitchen, she looked at me like I was nuts “f**k off, I’m not running a f*****g cafe Jack” she said as she lay down in front of me and started to finger herself. I watched her for a while before I mustered the energy to join in.

I woke up the next morning and she was standing beside the bed wearing a latex maid outfit that I had bought for her in the underwear store. Her enormous t**s were squeezed into the short white apron and her hair was piled up on top of her head. She was wearing black stockings and heels “good morning Mr Owen, reception sent me up to clean your room” she said and she was holding a tray. I sat up because I thought she had made me breakfast and although she looked good enough to eat I was still starving. I looked at the tray and instead of breakfast it had a c**k ring, a small silver smooth vibrator and a long double ended pink dildo with a bottle of strawberry flavoured lube and a can of wiped cream. “What’s all this? I thought you’d made me breakfast” I said but I couldn’t help but grin. “I’ll call down for some room service for you after” “after what?” I asked and although the double ended dildo terrified me I was intrigued where she was going with all of this. She placed the tray down, pulled back the sheet and I was still naked from the night before. The sight of her in her maid outfit had turned me on and I was at full mast. She took the lube and poured it into her hands and with a filthy grin she worked both of her hands over my hard on like an expert. I lay there totally at her mercy, her t**s bounced as she milked my throbbing c**k. I clenched my teeth as my c*m hit my stomach “Mr Owen what a mess, let me clean this up for you” she leaned forward and started to lick my c*m off my abs and it didn’t take long for my hard on to stir again. I loved when she was being extra filthy. She looked up at me and she was so pleased that I was hard again. She gently licked the tip of my c**k and ran small little kisses up and down my shaft and onto my balls. I watched as she started to deep throat me and although s*x with her was mind blowing my favourite was always when she gave me a blow job. Her mouth was out of this world. I’d asked her why her mouth felt like it was ribbed inside her lips and she had laughed and said it was my imagination. I was laying in our bed with the sexiest women alive sucking my d**k while wearing a sexy black and white latex maid outfit wondering how I’d got this lucky. Her head bobbed up and down before she suddenly stoped and sat up in front of me. I wanted to protest and ask her to keep going but I knew that she had a plan, and I was happy to go along for the ride. “So this tray of goodies.. what do you have planned for us this morning?” I said as she leaned forward and gently kissed me on the mouth “well” she said as she sat up and took the can of wiped cream and started to shake it before she squirted some onto my chest. “I thought I could put this in my p***y and put the other end in your ass” she lifted the double ended dildo with a huge smile. “Absolutely not” I snapped and she threw her head back and laughed and I couldn’t help but join in. “I knew you would say that. A big alpha male like you wouldn’t want to be dominated by anyone” she said as she licked the cream off my chest then she took some of the cream in her mouth and started to lick the dildo. I was mesmerised by her. I loved to watch her suck my d**k but the unbelievable feeling of being in her mouth would take over my whole body but watching her go to town on this dildo absolutely fascinated me. I hadn’t noticed that she had put lube on the other end. She lifted her little white maid apron and she was wearing the tiniest black lace thong. She pulled it to the side and started to rub the rubber head all over her c**t and then she smacked it hard against herself. When she finally inserted the lubed end of the dildo into her perfect tight smooth little p***y I was breathless just from watching her. I lay back and watched as she sucked one end and f****d herself with the other end. I couldn’t help but think I’d lived such a boring life before I met her. She was moaning and I ripped the front of her outfit to release her amazing t**s. I sat up and took the cream and put it on both her n*****s and roughly licked them clean as she continued with her dirty show. After a while I couldn’t take any more of this teasing, I wanted her. I grabbed the dildo out of her mouth and gently pulled it out of her p***y “take everything off for me, I want you naked” I demanded and she immediately did as she was told. She got off the bed and kicked off her shoes and removed her torn maids outfit. Then she put one leg on the bed at a time as she seductively rolled her stocking down and then threw them onto the bed. She was standing in front of me in nothing but a black thong and a little maids hat. I sat on the edge of the bed and pulled her by the hips towards me. I nudged her panties down until they hit the floor. Then I pulled her closer until her p***y was on my mouth. She squirmed and moaned as I teased her with my tongue and I could taste the strawberry lube. I looked up at her and she had her eyes closed and her head back and for some unknown reason I picked this exact moment to tell her that I loved her. I’d had plenty of opportunities before. There had been so many sweet tender moments between us but I’d always managed to hold myself back because we had only just started seeing each other. We hadn’t just spent that month screwing each other’s brains out, we had shared with each other. We had been vulnerable together but watching her beautiful face as I licked her clit.. I couldn’t hold back. “I love you” I said and I waited for her response. It took a moment because she was so lost in my touch but then she let out a little giggle and looked down at me. I felt like I was holding my breath waiting for her response “aww Jack, my p***y loves you too.” She said and she grabbed the back of my head and pushed herself onto my face. I lay back on our bed and she climbed onto my face and rubbed her c**t on my mouth. So declaring that I was in love with her hadn’t went exactly like I hoped it would have because she thought I was talking to her v****a. And although I loved her p***y, I mean, that went without saying, but I still felt a little defeated so I decided not to make the situation any more embarrassing by correcting her. She was on top of me riding my face and she was having the time of her life but I felt awful. I wanted to stop what we were doing and have a real talk with her about my feelings and I was desperate to know how she felt about me. This trip to New York with this beautiful, exciting woman was the best time of my life and I didn’t want it to end. But what if she would have told me that this was just a holiday romance. I would have been devastated. I wanted to know if we had a future back home in London. I was just about to pluck up the courage to ask her when she started to scream that she was going to c*m. I carried on licking her c**t until she cried out my name and I could taste her juices. “You are amazing Jack” she said as she climbed off my face. She always smiled after she orgasmed and it made me laugh every time because she looked so happy. Without missing a beat she said “now let’s see what else we have on this tray of goodies” she picked up the c**k ring and switched it on to vibrate. She took my hard d**k in her hand and put the ring over my shaft. It was a little tight but it felt good “are you okay?” She asked and I nodded my head. I was wrapped up in my own feelings and I had to pull myself out of it. She was like a s****l awakening and I was missing it because I was too concerned about how she felt about me. I finally snapped myself out of my own insecurity and pinned her to the bed. She squealed with excitement when I took her stockings and tied her hands one at a time to the headboard. She was so wet from her orgasm and covered in lube that I was inside her without any effort. I slowly thrust my d**k into her and she felt tight and wonderful. She pretended to squirm like she was trying to free her hands but I knew that it was just part of her game and I must admit it did turn me on. The c**k ring was buzzing away and it had two little rabbit ears that I had aligned with her c**t. Her face was flushed as I slowly rocked my hips back and forth. I was pulling my d**k out all the way out to the tip then bang my whole c**k back into her. This rhythm was driving us both wild. I felt around the bed trying to find the dildo. I could have easily just turned my head to look for it but I didn’t want to take my eyes off her for one moment. I finally found it and put the end of it up to her lips. She licked and sucked the pink plastic c**k as I slowly f****d her and I was in heaven. “You’re so f*****g sexy” I said over and over. She was like a dream come true until I could feel something cold at my ass hole. I looked down at her and I hadn’t noticed that one of her hands were free from the stockings. “What are you doing?” I asked but I didn’t stop slowly thrusting because she felt so good. “It’s the little silver vibrator, I’ve put lube on it already, it won’t hurt you’ll like it, just relax” I felt the smooth small cool steel enter my rectum and I must admit this was a first for me. She was incredibly slow and it let me get used to it. She switched on the vibration and although it was only a tiny little thing it really did pack a punch. I’d never even let her put her little finger near my ass before so I had no idea how good it could feel. I was lost for a moment because all of this pleasure at once was a little overwhelming. Then I opened my eyes when I heard her shake the can of wiped cream and spray it across her bare t**s. We both giggled at how incredibly horny she was before I started to lick the cream from her n*****s. She was softly rubbing my ass cheek and as I was grinding in to her I could feel the vibrator slipping out of my ass. It was completely smooth so there was nothing for me to clench on to. She very politely pushed it back in and I could feel that she was about to c*m. I felt her p***y spasm around my c**k and I increased my speed. By now all I could hear was my balls slapping off of her and the vibration from the c**k ring that was placed firmly on her c**t and her little silver toy that was now deeply inserted into my ass. She yelled out “FUUUUCKKKK JACK” as she came and I let go too. I felt my orgasm rip through my whole body as my iron hard d**k released a bucket full of c*m into her tortured little p***y. I lay on top of her until I’d softened and slipped out. There was c*m and lube and wiped cream all over the bed and I couldn’t help but worry what the real maids would have to say about all of this mess.