My sissy shemale ass needs a hard fucking

My sissy shemale ass needs a hard fucking
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Appreciating Bobby Hi I am 38 years of age,180 lbs, 5" 9 with a solid seven inches of sweet fuck muscle when fully erected.I love sex and I am open to explore all my fantasies and pleasures. My story begins with me coming home from my last day of work and into my 21 days long awaited vacation.I am a hard worker and have not had a proper vacation in years.My last day of work was a Thursday and my wife told me she had a surprise for me when I get home.

I love surprises and cold not wait.At dinner my wife gave me a envelope and what was inside made me feel special.It was an all paid 14 day vacation to the Caribbean just for me.

I was so excited that my wife and I had sex right on our kitchen island. Monday arrived and so I began my journey.Flight was good and arrived at destination on time and I loved the island at first sight since I have always wanted to go to The Bahamas. I then checked into my 4 star resort nestlled by the beach with lots of nearby trees and I was so sure that I will enjoy 14 days here.Now I went to the bar and decided that I'll get my holiday to a flier with some liquor.Next morning as I was taking in the sunrise I noticed my next door neighbour was doing the same.He was on vacation with his wife and son.

I intorduced myself and we had a good chat until eventually he introduced me to his wife and then his 12 year old son Bobby. For the next 3 days Tom, myself, his wife Tammy and Bobby spent some time together especially when we went on day trips and boat rides.We actually became friends.Day 5 and I was feeling a bit shaky like I was getting the Flu so I decided that I am not going anywhere.Tom rang me up to join him and his family to go on a Hiking trip and I quickly opted not to go and he was a little down but was supportive.Ten minutes later Tom rang me up and asked me if I can take care of Bobby while he and Tammy go on the trip of which he quielty whispered that it would be the perfect chance for them to get some alone time.

I had no problem with that since Babby seemed to be a well behaved kid.The time arrived and Tom came accross with Bobby and then left.Now Bobby and I had spoken a few times but mainly about his interestes and school. Bobby had brought his PS3 and went straight to gaming.I could not be bothered as long as he kept the volume down.

About an hour later I went to take a shower when Bobby came in to take a leak.I had a quick glance at his cock and it was small and soft and strangely I was getting aroused.Anyway he left and I finished and went to get some rest.I was feeling uncomfortable and a bit hot so I took off my shirt and was in my boxers alone. I could feel my body mucles starting to hurt a little.Eventually I went out to spend some time with Bobby since I myself was bored.I asked Bobby if I can sit and have a look at him gaming and he did not mind at all.About 10 minutes later I started to feel a little sleepy and dozed off on the sofa but i was not totally out but had my eyes slightly ajar.What I noticed next got my attention but I stayed calm.

I noticed Bobby watching at my body and would at times paused his game.Then as I was peeking at him I myslef was getting aroused.I felt a little bad at first but then the feeling was so nice of having an 11 year watching at my body.

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My cock started to bulge and I can see him just staring when I quietly asked Bobby "Do you like what you see?" He was embarassed and said he was sorry and I told him that it's ok.He can come closer and have a better look.Now my evil desires started to take control of my senses and I opened my eyes and invited him to come and sit next to me.

He did come next to me and I asked Bobby " What would you like me to do for you?" He paused a bit then said " Can I see your dick?" I was a bit surprised but said "ok".As I removed my boxer my cock was already semi hard and he was wowed.I told him to touch it and he slowly stretched his hand out and took hold of my muscle and the feeling was so nice.

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His hand was warm and soft.My cock went from semi to total hardness.I can see that he was loving the experience as well.

After about 5 minutes I told Bobby that I want to see his body now and he was so willing as if he knew what he wanted all along.As he removed his white shirt and brown short pants his beautiful tender body was exposed and I was now dripping with pre cum.

Then he removed his underwear and his little love meat was out and had some hairs around the base.I told him to sit next to me and I reached my hand out and held his 2 inch penis and it just sprang to life.It was now about 3 1/2 in lenght.AS I played with his penis he was enjoying every moment until I leaned down and took his young virgin cock in my mouth.

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Bobby's entire body was shaking and he just kept saying "It feels nice, please don't stop".I sucked his cock for about 5 miutes when He was starting to climax and he just blew his load in my mouth, It was not much but he loved it and so did I. When I was done I told him "my turn Bobby". He smiled and I told him to kneel down while I was sitting down.I guided his head and when my cock head entered his mouth it was heavenly.His mouth was so warm and soft. At first he did not know how to suck my cock but quickly figured it out.He was licking my tool and I loved it.He could only accommodate about 3 inches in his small mouth but I was grateful for it was making me feel much better.Eventually my body started to get more aroused I held his head and I shot my juices down his mouth and he gagged a bit but swallowed it all and then my cock popped out of is mouth.Surprisingly my cock was still hard and I had to ask Bobby.

Bobby can I fuck you in your ass? Bobby got quiet for a bit then said "Please don't tell my Daddy ok".

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I said "don't worry I won't". I took him to my bed and layed him down and grabbed my bottle of Petroleum Jelly and I started to grease up his anus.I could not help myself but to admire this young boy laying there all to myself.His ass was soft and as I lubed up his anus I realised that his entrance was a bit bigger than usual (I mean for a 11 year old I was expecing it to be more small).

I then pushed one finger in and started to massage his ass hole and he was loving it and was moving his ass around.I had to ask Bobby and so I did. "Bobby, have you ever taken anything up your ass before?". He did not answer, then I had to assure him that it's ok you can tell me.What Boby said next gave me spasms all over my body and a general go ahead and fuck that ass feeling.

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Bobby said " My Daddy does make love to me when ever my Mom is on business trips". I was amazed but was not ready to proceed.I then lowered my head and started to lick his hole and he was loving every moment. I then positioned myself behind him and placed my cock head at his entrance.I was a bit nervous but still proceeded. I pushed and 2" went in with little ease.His ass was so soft and warm inside.I pulled out and went back in all the way and he let out a sexy "awwwwwww".

I can literally feel his anal walls gripping my cock and we both were enjoying this sweet fuck.I then started to fuck Bobby's ass and boy oh boy did he take my entire 7" of muscle.I was in pure extasy and as I made love to this young boy I wanted this to last for a long time.I reached round his waist and grab his cock and it was wet with pre cum and I was buried deep in his love hole.I then pulled out and told him to get on top of me. I layed down and lowered him ontop my wet and hard cock.AS I entered Bobby once more he let out a mild "awwwwwwwwwwww" and then he started to bounce on my tool.I was amazed how well he fucked my cock.After a few minutes I was ready to cum again and I grabbed his waistline and was lifting and pulling him down on my cock harder and harder until finally I started to shoot loads and loads of my love juice deep up on his ass.It was so amazing.I made him sit on top me until my cock went limp and he slowly rolled off.

We layed in bed together then both hit the shower and cleaned up. I was felling so much better, no more flu like symptoms. Bobby went bcak to playing his games when about 2 hrs. later Tom and Tammy returned.

They picked up Bobby and went to their room. Later that evening at dinner Tom approached me and asked me to have a few drinks with him at the bar.I agreed and after 6 rounds Tom quickly asked me " What do you think about the idea of me and him fucking Bobby together?".

I was so embarassed but he quickly told me that Bobby told him about the great fuck we had today and that Bobby wants the two of us to Fuck him.I agreed and then Tom told me that we have to escape his wife and he will take another hike but this time just him, myself and Bobby. I knew I was gonna enjoy this vacation.