My Sissy Beginning
It started when i was a young boy,the youngest with two older sisters.I would always sneak into my oldest sisters room and steal her panties.She always wore the cute string bikini silky style.I would wait till the evening time when everyone was in bed and try them on. I just loved the way they felt,the silky smooth material against my naked skin.
As i got older,threw my teens and twenties I always tried on my girlfriends panties,my cock would get so hard from the look and feel.I would always curious about what it would be like being with another man,while i was wearing cute girly cloths.Well..that day came when i was 23 years old.I thought it was going to be a typical day.Before i left for work i decided to grab a black lace thong that i kept from my ex girlfriend,stuffed it in my jacket and off to work i went.
Lunch time rolled up and i left to go to the river where i usually ate lunch.I didnt bother eating and started walking around looking for a nice hiding spot to get undressed and slide the cute lace thong on and rub my cock for a while. As i was looking i heard somthing behind me,i quickly turned around and there before me was an older man on a mountain bike. He spoke in a soft voice and said “Oh..hi there”. with i quick reply i said “How ya doin today?” he sits down on a small dirt mound and says “Oh..im just out looking”.. being more than curious i asked ” So…what are you looking for?” he said “Just looking for a little fun” and reached down and released the button and zipper on his pants and pulled his half hard cock out stoking it a couple times. I was in shock that this older man pulled his cock out!
The shock wore off a bit and i couldn’t take my eyes off of his cock. At that point i knew i was going to have sex with this man.I looked at him and with a shakey voice ” I think we can have some fun here”. he smiled and i quickly looked around and i spotted a nice over grown area.I said “lets go over there” i headed for the area and he followed just behind me. I pulled off my jacket and turned around to face him and he already had his shoes off and was removing his pants. his nice cock was bouncing around and it looked so good. I told him i had a surprise. and with a smile he said “ok” I kicked my boots off and and pulled my pants off,my cock was already hard and leaking precum.I grabbed the panties from my jacket and slid them on over my naked skin.my cock was throbbing at this point. I asked the man ” so..what do you thing?” he quickly said ” You look so sexy!” He stood there looking at me, i stepped close to him and pressed my hard cock against his,staring down watcking his meaty member rub against the black lace thong.
After a few minutes of pressing against each other and him running his hands over my ass i noticed some precum leaking from his nice cock.I dropped to my knees and with his cock now in my face i told him ” Let me hlp you with that” without thinking i wrapped my lips around the head of his cock, sucking up the precum.It tasted so good i started sucking more and more,sliding his hard meat in and out of my mouth. I reached down and pulled my quivering cock from the side of the panties and started troking and rubbing my self. Hearing him moan from pleasure and telling me it feels so good made me reach my peak of being curious, and i popped his cock from my mouth and asked him ” you want to fuck me?” he said in a quick voice “Oh My God..Yes!”
I told him he could lay down on my jacket cause i wanted to be on top like a girl would. He then laid down and on all fours i crawled over to him giving him a couple kisses and quick suck to the head of his throbbing cock. I then swung a leg over him and straddled him.I felt his hard juicy member pressing against my ass.I moved my hips back and forth while reaching back spreading my butt cheecks and pulling my panties to the side.He reached down taking a hold of his cock,tilting it up as i moved my hips back.I felt the warm head press againt my tight hole.I took a nice glob of spit from my mouth and rubbed it on his cock and my hole. I took a hold of his throbbing hardon and rubbed the head against my soon the be “pussy” and started to lean back into it.I felt the head slowly enter and i pushed back a little more.it started to hurt for a second but felt so good at the same time.He then took a nice glob of spit and rubbed it on my boi-pussy and his cock. I thought it was now or never and pressed back to him harder and felt his cock slide deeper in.I started to rock back and forth as he lifted his hips to meet me.
With each time i felt him go deeper inside my now “pussy”. With both his hands holding my ass,he held me in one spot and started fucking me.After about five minutes or so i hear him with a shakey voice say “im about to cum” I thought to my self,”Well…If im being fucked like a girl,might as well cum in me like one”I leaned down towards him. as to be on my knees and elbows and whispered “Cum in my ass”. A couple more thrusts i felt him tighten up as his cock went deep in my pussy,I felt the hot cum start to squirt in as his hard cock throbbed and pulsed. The feeling was so over whelming i started to cum as well squirting warm cum on his bare stomach.
We both took a moment to get out brains to work after out orgasms.still leaning down towards him. I said ” We need to make this a regular thing”. He said ” Yes..yes we do” I got up off of him and i felt his cock slide out of me and then i felt the still warm cum start to leak out of my now pussy. We both got dressed and he told me where he lived for future meeting which wasnt far from my work at all,like five minutes. I did meet up with him often at his place. During lunch hour and even on the weekends. I started buying more and more girly clothes,panties,lingerie,stocking and he’d even buy stuff.
I enjoyed every encounter with that older man. I lost count how many times. He was my First and you ALWAYS remember you first. I can admit I love cock and being fucked like a porn star…I’m a Sissy Slut