I love feedback to my stories. Please email me at jacki_j@rocketmail and let me know what you think. Enjoy!! LOOSE ENDS 17
When you go to the horse races you always see women dressed in their best dress and big hat enjoying a day out in the sun. They always look so royal and fancy. Mary is one of those women. She is a middle age glamorous woman who always looks like she is on her way for a day at the races in her best dress and big hat. She turns up for work in her big hat and she'll attend a Sunday barbeque in her big hat. She always seems so proper and polite that she has to be considered the ideal role model for her children. So I thought.............
I had known Mary for a fair while ever since I did part time work in the mail room at the Law firm. She worked in the Finance department and she really did come across as the real proper and innocent finance person. That was until I saw drunken Mary at the company Christmas party. This was a REAL different Mary indeed.
I was standing at the bar talking to a few of my colleagues when Mary slotted in next to us. She was clearly drunk as was I, as were we all actually. The talk really did not centre on anything specific that I can remember but what was intriguing me was the focused looks that Mary was giving us both. It was seductive and piercing at the same time. It was a look to say that she was going to take us home and rape us both. I think my colleague got scared and he took off to the toilet soon enough leaving me alone with Mary. We talked some more and we both had another drink. She was clearly very drunk by now and said that she had better go home. Being the "Gentleman" that I was I offered to walk her to a taxi to get her home. She accepted the assistance and we made our way outside. Standing on the curb I hailed a taxi. As it pulled up I was preparing to say goodbye and she leant over for what I thought was a kiss on the cheek. To my surprise she panted one squarely on my lips and locked them there for several moments. The taxi pulled up and she waved it away.
"So I guess your not going home yet?" I said
"Not yet honey, not until I have sucked your cock dry"
Holy shit!!! I thought to myself. Is this the same Mary?!!!
"Aren't you married Mary?" I asked
" Yes, I'm married and so very horny. Since having the kids my husband hardly ever fucks me" She slurred drunkenly. " Jack will you fuck me?"
So I have been fucked by many older men before and only ever been with one older women when Bob and Irene has their way with Jacki but this was very, very different. But who was I to say no to this drunken but clearly in need of a good fuck middle age woman.
" How could I resist" I smiled back to her. " Where to?" I asked "Lets go to the Radisson and get a room" she said. The Radisson is like a 5 star hotel and would not be cheap but she clearly wanted to be laid in a classy environment so I did not argue.
We walked in and Mary requested a room. The lady at reception asked what type of room. Mary in her intoxicated manner didn't really try and hide why we were there and just told her to give us any room with at least a double bed in it.
We entered the room on the 7th floor. Within seconds she was all over me and my clothes were being ripped off. She threw me onto the bed and started kissing me ferociously. I was trying to get her clothes off but she was taking me down with such force it proved difficult.. She eventually stood up and started to strip for me. She was wearing quite a nice aqua blue evening gown and she slipped it off her shoulders to reveal a sexy blue lace bra. She lowered it down over her hips and that revealed some sexy and elegant lacy blue panties and to my pleasant surprise black suspender stockings. She was a classy old horn bag, make no mistakes about that. She was very soon back on top of me. She was quite passionate with the way she kissed me. It wasn't big sloppy tongue kisses but quite gentle kissing. She started kissing my neck and worked her way to my chest. She kissed me all over working her way down but stomach and soon stopped at the top of my pants. She undid the belt and button and started to slide them down my legs. I was wearing boy underwear on this night so no surprises yet. She lowered my underwear releasing my very hard and smooth cock from their pouch. She saw my lack of pubic hair and looked at me with a smile. I think she liked what she saw. I think this was evident when she quickly grabbed my throbbing cock and took it in her palm stroking it all so gently. Damn it felt nice, it felt even nicer when she lowered her head and took the tip in her bright red lips. As I'm not that largely endowed it didn't take her much to take my entire length in her mouth and she son was giving me a nice slow bow job. It was so very different to the sloppy and slutty blow jobs that Jacki likes to give but it felt amazing. She blew me for a decent length of time and it always had such elegance about it. Soon she lifted her head and stood up. She unclipped her bra and took it off exposing her quite large bosoms. They still had decent enough shape after two children. She then started lowering her panties soon exposing her quite hairy and apparently sexually neglected pussy. She moved over and laid on the bed next to me and turned her head towards me.
"Make love to me Jack" she asked all so delicately. Her drunken and horny demeanour had suddenly been replaced by an almost guilty and scared character knowing that she was about to cheat on her long time husband and the father of her children.
I paused for a moment wondering whether this was the right thing to do. It wasn't as though I would never see her again. I'd see her every time I walked into that office. "ok" I said softly.
She lay there looking up at me as I got in front of her. I looked down at her pussy. Harshly I thought to myself " NO chance in hell I am eating that pussy!"
I lowered my body down on top of her. She grabbed my cock in her hand and guided it towards her waiting pussy. I felt the moist and warm entrance against the head of my shaft and I pushed slowly in. She moaned softly as I entered her loving hole. Slowly I pushed in and out of her. She gave me such a loving look as I slowly gave her a long over due fucking. It went on for a long time as I slowly kept pushing as deep as I could in and out of her. She didn't seem to show any interest in changing positions. I think she was getting great pleasure out of a simple but joyful dicking. After seemingly for ever I know I was getting closer to coming. Then as I knew I was about to I withdrew and came all over her stomach. Yes I know it's fucking boring cumming on a stomach but I think this occasion called for it. She obviously wanted it to be a gentle love making session, which I must admit was quite contradictory to her earlier statement which I quote " Not yet honey, not until I have sucked your cock dry"
We laid in bed for a while longer. Obviously she had to get home to the family and eventually after a bit of chit chat she got up and showered. We were soon dressed and checking out of the hotel 2 hours after checking in. The look the guy at the concierge desk gave me was priceless. Son Mary was in a taxi home to her family and I made my way home as well. What an interesting night!
It was the week after next that I was in the office again. About half way through the morning I had to make a deliver towards Mary's bay. I felt a bit awkward as I approached. Our eyes met but this was proper and elegant Mary in the office. IN the most professional manner it was as though nothing had ever happened. Maybe she forgot I thought as she was very drunk. Our meeting not long after in the kitchen soon told me that she hadn't forgotten when I felt a pinch on the ass and turned around to see her there.
She slid me a note. " Meet me after staff drinks this Friday" I just nodded and went back to work with my water bottle.
I met Mary on that corresponding Friday night. We once again went to a hotel, though this time not quite as an expensive establishment. The experience was identical to our previous encounter. We "made love" slowly and I came on her stomach again. It was very uneventful sex. A few weeks later we met up again and had the same experience for the third time. It was on the bus ride home that I came to a conclusion. This was BOOOOOORRINNNNGG. I don't do this shit. I don't do slow love making, I do slutty hardcore fucking. If she wanted me to continue fucking her something had to change. I appreciate that I was fulfilling her middle age sexual crisis and all but I'm sure she could have found someone else to give her 47 year old pussy the slow dicking that it seemed to enjoy. I had a plan.....
I decided I'd give Mary one last chance ( I know, how nice of me). We did the deed again and laid in bed following it.
I asked " Do you have any fantasies Mary?"
"It's been a long time since I really fantasised Jack, well apart from fantasising about you dear that it" she said with a smile
" Well tell me what you used to fantasise about" I asked
" Well............. I was always intrigued about having a threesome" she said shyly "With 2 guys? or girls? or a mixture?" I asked probing.
I could see her getting uncomfortable talking like this but I wasn't about to let up as she said " I always wondered about being with another women and also the thought of being with two men."
" Interesting" I said " But it never came through did it?"
" No it didn't" she finished.
We organised to meet again and continue our affair. Though I had other plans for our next meeting. I had a few friends that I was going to invite including my very best friend Jacki. If it was to be possibly our last meeting I might as well make it one to remember.
I needed another man to invite and I had just the person. I wanted someone real assertive and old Michael was just the man. It had been a while since I say Michael but I had his number and gave him a call. When I asked him for some three way action with Jacki and another woman he was more than up for it.
That Friday I packed my bag with everything I needed that night before heading to work. I made sure that I locked my bag in a locker that day. I met Michael just near work and we made our way to the arrange hotel. Mary had sent me the room number by text message so we knocked on the door. Mary was not expecting two of us to arrive and was very shocked when the door opened.
" Mary, this is Michael and we're here to make your fantasy come true" I said as we walked in. Michael doesn't have the greatest people skills but he said hello adequately enough.
" Uhhh, Jack I'm not sure about this" Mary said almost scared
I moved close to her and touched her on the arm reassuringly " Mary, it's ok, you'll enjoy this"
Mary was very hesitant. I definitely would not make her do anything that she really didn't want to do but after we sat and had a few glasses of wine and talked a little while she started to loosen up a bit. and then Bob started to be his charming self.
" Why don't you show us what you have on under that dress" Bob demanded
Mary stood up and started doing a bit of a strip tease for us. She was wearing some pretty red lacey bra and panties on this night. Michael liked what he saw and as she was stripping he had pulled his big cock from his pants. He was already hard and all 9 inches were standing tall. he stroked himself and Mary looked at his rod with a look of shock.
"Come over here Mary" Michael told her and she obliged moving over next to him on the bed. He grabber her hand and placed it around his cock and she gently pulled. " Why don't you give it a suck" he said.
She lowered herself down and placed her lips around his head and started slowly sucking Michael big stick. I knew Michael would take the slow shit for long and soon had his hands on her head and started pushing her down lower and lower. I heard her gag a first time and then a second time. He pulled her up and let her breathe. She just looked at him with a look of despair on her face. He pushed her back down and she went deeper and deeper again and was gagging soon again.
" Relax Mary, just open up as much as you can and relax" I advised her being the expert blow job giver of big cocks that I am.
She did start relaxing and soon was working on his big cock.
" I'll be back in a moment" I said and grabbed my bag and went to the bathroom. I very quickly got changed into Jacki. Matching red bra and thong, fake boobs, black skirt and lack singlet finished off with black fishnet stockings. Finally I put on my wig and make-up and went back into the room. It was a very quick transformation tonight.
" Hi I'm Jacki" I announced as I walked in. Mary looked at me in disbelief.
Mary was stunned, " Uhh, hi Jacki" she replied
" I sure hope that Michael's being nice to you" I said. "He can get a little rough sometimes"
" So I have seen" Mary said back
" Can I join you on the bed?" I asked
Michael moved over and said " Yes you can" not really giving Mary any choice. I sat on the other side of Michael and said " Don't stop on behalf of me Mary" as Michael pushed her head back down to his shaft again. I watched her briefly and then grabbed the base of his shaft with my hand. He kept her head down there but I could see her look at me with shock once again as my hand choked his rod at the base. She really had no idea what I was capable of. She soon would though!
As Mary sucked the upper part of Michaels cock I stroked the lower part but I soon wanted some as well. "Does that taste nice Mary?" I asked. "Do you mind if I have a taste?"
Michael allowed her to release his rod from her mouth. " Be my guest sweetie" she said out of breath and still looking at me with uncertainty.
I moved in for my turn. I opened my lips and slid them as far down his shaft as I could. only fairly he grabbed my head and pushed me right down as well and I also gagged briefly before relaxing my throat. I started sucking real hard and was son sucking him ferociously up and down his entire length. Mmmmmm it tasted and felt real nice. Saliva was leaking from my mouth as I went to work savagely on him just as he likes.
Mary was starting to relax a little now and I heard her give me a satisfying Mmmmmm of approval. I moved away and motioned her back in. She sucked a bit harder this time taking my lead and we took turns in blowing Michael for a good 10 minutes or so.
While she was blowing him I said " Mary likes to be fucked slowly on her back Michael. Do you think you can oblige?"
" Of course" he said. Mary stopped sucking him and moved further up the bed and rolled onto her back. Michael positioned himself between her legs. This rod was about to test her a lot more than my tiny one did. He pushed the head into her pussy. She moaned quite loudly as he entered her. Soon he was pushing deep into her slowly just as she liked it but once again I knew that this would not last long. Within moments the tempo increased and soon he was giving her pussy a considerable pounding and her tits were wobbling in motion with each thrust. He kept pounding and her moaning got louder and faster. I leaned over and took a tit in my mouth sucking on her nipple and biting on it to make it real hard as he fucked her harder and harder.
Soon he stopped. " On all fours Mary" he demanded. She was clearly getting into it now and she quickly did as asked and rolled over and knelt as requested. He got in behind her again and soon was thrusting into her deep from behind. I moved around in front of Mary and pulled my tiny clitty from my panties and put it in Mary's face. She knew what to do and began sucking on my hard girly cock. I bet she wasn't expecting a big 9 inches in her pussy and a smaller girly cocking her mouth at once a few hours ago. We continued to spit roast her, he pounded her and I pushed as deep into her mouth as I could.
I was ready though, " Can I please have a turn Michael?" I asked nicely " Do you want a fucking Jacki?" he asked back
" Yes Please" I answered
"OK then" he said
I got onto all fours beside Mary. he pulled out of her and over behind me. Boy was I looking forward to this. I felt his tip push against my asshole and instantly he just shoved it in. " that prick!" I thought. he didn't even spit on my hole or anything and just shoved it in dry user her pussy juice as the only lube. It actually hurt a bit but I was soon in heaven. He really can be quite brutal as he was soon really fucking my ass so hard. Luckily I love it hard and the harder the better. Mary watched and I turned to look at her.
" God this feels good Mary" I said to her. " How does it look?" I asked
" I am totally in shock" she said
" Can you see his big cock burying deep into me" I asked
" I sure can Jacki. He sure is deep"
Michael continued pounding my slutty man cunt, really giving it to me. " Fuck me Michael, fuck my ass harder, HARDER" I demanded from him. " Mary make him fuck me harder, push him into me harder" I told her and he put her hand on his ass and pushed it in motion with him. " God I love a big cock in my ass Mary. It feels amazing" I said in pleasure as she watched Michael ravage my hole from behind.
Michael was puffing hard and was getting close but it was way too soon so I pulled away and he dropped out of me. " Mary" I said, " It's your turn".
"Ahh NO I don't think I can do that" she said
" Don't worry, I'll be your first. I wont let him near it" I tried to say to convince her. " Come on, why not give it a try"
" ummmm.......ok, but only if you do it" Mary hesitantly agreed. Mary got on all fours on the bed next to me and I moved out behind her. I grabbed some lube from my bag and squirted some onto her hairy asshole. I used my finger and rubbed it all around and then pushed one finger in. She moved a bit startled. I worked my one finger around a bit inside of her ass making it as wet and slippery as possible. Soon I thought she was ready. I wiped some lube onto my little prick and pushed it in towards her tight hole. She was very slippery and I slid in surprisingly easy. I just pushed it in and held it there. She moaned a bit and stayed very stationary. I pulled back and pushed in again to another moan. Jacki was breaking this middle age woman's ass in. Now this was different. I started to go a bit faster and a bit faster again and soon enough I was fucking her ass at a steady rate. She felt tight around my little cock as I fucked her even harder. She was moaning steadily now as I fucked her ass more and more. Michael was itching for a turn. I could see it in his face but was she ready. I gave her a real fast and hard 30 seconds or so really trying to loosen her asshole as much as my small sissy cock would allow it to. I then nodded at Michael is if to say " Your turn"
I moved out from behind her and Michael moved in. She look at me not sure about this. I told her to relax and just let her body adjust. I know how she must have felt when Michael just shoved himself in there though. I could see the look on her face as his 9 inches opened up her not so recently virgin asshole. I put a hand on her back as Michael too one thrust and then another and was son pounding her chubby middle age ass with his big cock. I was getting really turned on..
" Mmmmmmm Mary, I can see his big cock going deep into your ass. It looks amazing, does it feel good Mary?" I asked her cheekily. She stayed pretty silent and just kept moaning and had a look of pain and punishment on her face.
I was getting really worked up and nasty now. " Yeah give it to her Michael, drill that asshole." He did as I asked and was fucking her ass so hard. I don't know if she was crying or what but her face was real red and he fucked her so hard.
" Mmmmmm I want to taste her on you" I said and pulled his cock from her ass. I quickly shoved it in my mouth and I could taste her ass juices on his cock and it certainly had an aroma about it as well. I sucked him clean and he shoved it in her back door. I soon pulled him out again and cleaned him off. we kept going like this and I would clean off whatever came out with his cock and he would put it back in again.
I needed him inside me again. I laid on my back next to Mary and he moved in between my legs. " Hold his legs up Mary" Michael demanded. She grabbed my right leg and pulled it out and up and he grabbed my left leg. Opening me right up. He put his cock to my hole and rammed it in again and soon started fucking the shit out of me. it was awesome as he rammed me hard again like he does the best.
" Have a taste" he said to Mary grabbing her by the hair and pushing her down to his cock. She tried to hesitate but he gave her no choice as she took his cock deep in her mouth and cleaned my juices off him. He entered me again and then made her eat it again. I loved watching him pull his cock from my ass and put it straight in her mouth. She had to taste whatever was on there.
Soon it was Mary's turn again. " Ride him Mary" I told her and he laid on the bed. She straddled over his frame and I grabbed his cock. She sort of got into position to line her pussy up with it but I aimed it at her ass. She lowered down and I guided Michael cock ever so deep into Mary's asshole. He thrust up, she moaned, he thrust again she moaned again. it got faster and faster. I moved in behind her and grabbed her tits, squeezing them and her nipples as Michael driller her ass again. I really wanted to fucker her ass again but Michael was going berserk pounding her from below and I don't think she was up to a DAP yet. I lowered myself behind her ass and started licking Michaels cock as it thrust in and out of her tasting everything she had again. Michael breathing got faster, he was going to cum. he kept going and I didn't stop him and very soon I tensed and started shooting load upon load up her asshole and into her bowel. I pulled him out and sucked him dry and then quickly got in behind Mary and started eating her ass and licking and sucking everything out that I could ( Yes I can see the irony that I wouldn't eat her pussy but I'll eat her cum filled asshole) I could taste Michaels cum and whatever else as I licked and sucked and licked again.
When I'm Jacki I don't usually get to cum but fuck it. I wanted to come this time!!! I got on my knees and moved in behind her. I put my sissy cock in her ass and started pounding away again. I was pretty worked up and soon I was about to cum. I Pulled out and moved around in front of her shoving my cock in her mouth and soon I shot my little load deep in her throat. She gagged again but I wouldn't take it out.
" Swallow it!" Michael demanded and eventually I felt her gulp it down.
Poor Mary. She really enjoyed making slow love but we had just turned her into a right royal anal whore. Possibly for one night only but an anal whore none the less.
Michael cleaned up and pissed off quickly like he always does and I showered and got changed. She then showered and I waited for her.
She came out of the bathroom. " Are you ok?" I asked. " Sorry but Michael and I get a bit carried away"
" I certainly wasn't expecting that when I arrived this evening. If was definitely different. Oh, I enjoyed it but there was things that I would never do again and only did in the heat of the moment. Anyway, as you said before, you just have to give things a try."
We made our departure soon after. That was the last time I was ever with Mary. I think she certainly decided to be a family person after that night. Well I think so anyway. maybe she just found someone else to play with and if so good for her. Now when I saw her in the office it was as though we were strangers again. Not that it bothered me too much. I got plenty more people to play with.