📚 the-apple-doesnt-fall-far Part 1 of 1
Part 1
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GAY SEX STORIES

The Apple Doesn't Fall Far

The Apple Doesn't Fall Far

by Lifelongsissy
9 min read
4.52 (5500 views)
crossdresser
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When I was eighteen my best friend and I were very close. He knew that I was a Crossdresser and that I loved cock. Although he knew for a long time he never showed any sexual interest in me. Which was fine with me as I valued his friendship more than I could say. But our relationship was going to change in a huge way the summer we graduated high school.

He had a pool at his house and we spent every minute we could lazing on his patio. About a week after graduation I asked if he would mind if i wore a bikini as I really wanted a bikini tan line. He said "That's going to be weird but you can wear whatever floats your boat."

After about two weeks of laying out in the sun with plenty of suntan lotion I was very happy with the results,a killer ultra feminine set of top and bottom tan lines.

One particularly rainy day we were stuck inside watching videos on MTV and a video featuring girls in Bikinis came on and he blurted out "So how did the tanning turn out?"

"Fucking perfect just how I hoped" I replied.

He said "Let me see" So i stood up and pulled the side of my jeans and panties down a few inches revealing the line from the string side of my bottoms on my hip.

He said "Wow that's really hot."

Jokingly I asked "What's hot my pretty pink panties or the line?"

To my utter shock he replied "Both".

"Why are you being an asshole all of the sudden?" I snapped back.

He asked "Why do you think I'm being an Asshole when I was giving you a complement?"

I told him I thought he was teasing me.

He assured me he was being genuine.He admitted that watching me parading around the last couple weeks in a Bikini,with my long hair in a girl's style ponytail and my pink toenails,he noticed how feminine and actually sexy i was.He confessed,several times he got hard watching me apply lotion on my body. And he actually looked forward every day to me asking him to apply it to my back.

Now he's really teasing me I thought. And said as much.

He said he was "dead serious"and he could prove it if I didn't believe him.

"How?"I asked.

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"Come up to my bedroom and I'll show you" So we went up to his room and he propped his back against his headboard with a couple pillows and said "Show me".

"Show you what baby?" I teased as if I didn't know.I just needed the hear him say it.

"The panties then the tan lines, all the tan lines," He snapped.

I'd known him long enough to know he was serious so I removed my shirt to show the lines on my chest and he folded his arms and ordered me to keep going.

"Show me the pretty pink panties now" He ordered in a very authoritative tone which made my dicklet twitch.I turned away from him and unbuttoned and unzipped my jeans and let them fall.

i heard him mutter "Oh fuck your ass is so fine,now turn around."

I said I didn't want to because his ordering me around had my dick so hard and it was leaking quite a bit.

He seemed to be getting the picture. And to my delight became very authoritative and barked. "Take your hair down and turn the fuck around now Bitch!"

I did as I was told and he commented how wet my panties were. And ordered me to take them off so he could see my Bottom tan line.

I was shaking as I stepped out of my panties and did a very slow turn and when i was facing away from him He ordered me to get on my knees. I complied.The forcefulness in his commands was turning me on so much I was literally shaking.

He said "You wanted proof" I could tell he had gotten off the bed and was coming around me but I was in such a submissive state that I kept my eyes down staring at the carpet. As he stepped in front of me he barked "Here's all the proof you need" as I raised my head i was staring directly at his gorgeous 5-6 inch rock hard cock and it was beautiful.

"Open your fucking mouth" he ordered and all I could do was open my lips and involuntarily reach out and grip the shaft and guide it into my mouth.He tasted so fucking good so I completely lost sight that this was my best friend feeding me his perfect cock and I took it balls deep and milked the head with my throat muscles.He let out a loud moan which spurred me on and within two minutes he was fucking my mouth with rapid long strokes.He held me by both sides of my head by my hair and pumped wildly until I felt his cock start to spasm and he let out a growling noise and spurt after spurt of his delicious cum filled my mouth and I desperately swallowed all he could give me and continued to suck every remaining trace of his gift to me out of his piss slit.

When his orgasm subsided we climbed into his bed and under the covers and fell asleep with him spooning me from behind.

We must have slept for a couple hours but I awoke to him gently rubbing my dicklet and his hard cock between my ass cheeks so I was backing into him and grinding on his member and he rolled me onto my stomach and I felt his slimy cockhead against my hole and in one painful thrust he was buried in my cunt to the hilt then he grabbed my hair and pulled us up into a Doggie style position and started humping me wildly.It was then I felt an uneasy feeling of being watched and I caught a glimpse of his Dad in the mirror watching us from the doorway,I could see he had his hand down his pants but I quickly got lost in the pleasure of the amazing pounding he I was getting I couldn't have cared any less who was watching.

After about three minutes of animalistic fucking he told me "Im coming bitch "

I begged him to fill my cunt and he delivered and I had an amazing whole body orgasm that nearly made me pass out. He pulled his cum covered cock out of my sore Boi Cunt and reached for his shirt to clean it and I stopped him and begged in my sweetest Femme voice "Please let me clean that for you Sir" he handed me the shirt and I tossed it on the floor and he looked at me as if confused until I leaned over and proceeded to lick it until it gleamed.Then I slurped up the puddle i left on his sheet.

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He noticed the time and said "Oh fuck my Dad will be home any minute" so we got dressed and went downstairs and his dad was sitting on the couch drinking a beer we said Hi and I left with his cum leaking into my panties. I didn't tell him about what I saw in the mirror.

Later that evening he called and told me his Dad knew and had seen my tan lines. He told me he had a talk with his Dad and he was going with his Mom tomorrow to help her move some things at his Aunt's house and would be back the following day and that his Dad wanted to talk to me about the situation and to go see him tomorrow.

All night I tossed and turned thinking about what to say to my best friend's father who knows his son fucked me.

The next morning I douched and shaved as i did every two days and put on fresh white satin panties and matching bra a loose fitting sweatshirt and my jeans and made my way to my friend's house.

I rang the bell and nervously waited and His Dad opened the door and invited me in. I followed him to the living room he had me sit on the couch and he sat in a chair across from me.

After a couple of minutes of awkward silence he said "I know that boys experiment in different ways with each other," I listened intently. He asked if Will (his son) and I were gay?

I told him I couldn't speak for Will but yes I was. Then he asked me to explain the pink panties on the floor and the unusual tan lines he saw on me.

I explained that I was what people would call a Total submissive Sissy Faggot And that I have been wearing only women's underwear for a while now.He asked if I was wearing them now?

I sheepishly told him I was. And I apologized for what he had seen the day before and that it was something that happened very spontaneously. I told him how When Will got dominant "I couldn't help myself."

He asked If I react like that often I told him I didn't understand why but when I am told to do something by a real man it turns me on so much.

As we talked I noticed a bulge appearing in his shorts when he said "Help me understand,you will do whatever a dominant man asks you to do?"

I shook my head no and said "Whatever he tells me to do. There's a big difference."

Out of nowhere with a stern voice he said "Get up and take your shirt, pants and shoes off now."

I did as he told me and I was standing in front of him in only my bra and panties. And could tell by his bulge he liked what he saw.

"Come here and take my clothes off" again I obeyed pulling his shirt over his head then running my hands over his hairy chest then dropping to my knees and unbuttoning his shorts and pulling them down and then his underwear his cock was fully hard.A bit smaller than Will's but still gorgeous.

He put his hand on the back of my head and pushed it towards his dick I got the message loud and clear and took it in my mouth and started a slow and sloppy blow job.After about five minutes he pulled me off of him and directed me kneel on the couch with my head on the back of it and not to move and he left the room. He returned a minute later with a bottle of lube he pulled my panties to the side and applied a generous amount to my cunt and then lined up his cock and very gently entered me. I took him smoothly and easily and he leaned forward and started kissing my neck and my ear telling me how sexy and tight I was so I turned my head and we started kissing he explored my mouth with his tongue and i was in heaven.

He fucked me like that for about ten minutes then started to steadily pick up the pace until he was flat out slamming my cunt. I had already cum once and the second time I came he said he could feel my cunt contracting on his cock and he grabbed my throat and buried his cock as deep as he could and I could feel it twitching with every rope of cum he deposited in me.then he let go of my throat and kissed me deeply,my panties were a total mess.

He had me get dressed and told me if i ever fuck Will again he wanted it to be with him and about a week later we actually had that threesome and it was amazing.

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