Mile High First Time

Literotic asexstories – Mile High First Time by barely18cock,barely18cock
How I Lost My V-Card, or The Mile High First Time

It all started when I went on a trip this summer. I was going to visit my grandmother who lives in Washington State and since I live on the East Coast, it’s a looong flight out and back. This is the story of the attractive young lady I met on the airplane, and the story of my first time ever. I should probably start by describing myself.

I’m about 18 years old and stand at about 5’6″, short blond hair, square jaw line, kinda on the skinny side. I was wearing a button up shirt and jeans, my necklace and a sort of sporty watch I always have with me as well as my cap, which I never leave home without. I have a good personality; I’m generally humorous but can be serious and suave when the situation calls for it. I’m not afraid to say at this point, I’m well hung, I’m between 5 and 6 inches soft, and between 8 and 9 hard.

As my trip started, I boarded the plane and was thinking about this porn video I saw the premise was that the flight attendants on the airplane were also personal sex slaves, so I was feeling ready to go, if you know what I mean. Believe me, the fact that I was horny was showing. Anyone around who looked at me could instantly tell, from the bulge in my pants, that I was in the mood. As I boarded the plane I was getting a lot of funny looks and people blushing and looking away, expect one person. She was about 20 years old, average height, a bit shorter than me. Her face was narrow and kinda cute, she had an adorable face and clear blue eyes. Her hair was blond and about shoulder length she had on slim black framed glasses. She was wearing a thin white blouse, but no bra, and in the heat her sweat was making it obvious that she wasn’t wearing a bra, and on top of that, it was apparent her nipples were rock hard. She was wearing black pants, almost skin tight, and a bracelet which was made with blue stones, it really set off her eyes and made them stand out. All in all, she was gorgeous, easily the most attractive woman on the entire plane, and that included the smoking hot airline stewardesses.

What was unique about her, is she knew I was horny and instead of looking away, held my gaze for a long time, she made eye contact almost seem hot and steamy. It was as if she knew I was horny and wanted me to know she was too. So about half way through the flight she starts to walk down the aisle wearing black sandal-high heels. God, even the way she walked was sexy. As she walked by me she looked right at me, her shirt still slightly damp and translucent, reached up and grabbed her breast and rubbed it while she walked by. By that point my cock was standing to attention and I had to pull down the tray table to hide it from the other passengers I was sitting next to. She walked back to her seat all the while swinging her perfect, smallish but well shaped, ass at me. And when she was almost out of sight, she reached back and slid her hand in her back pocked and rubbed her ass for me.

About ten minutes later she walks by me again to go towards the bathroom and this time she winks at me and nods her head towards the back of the airplane. Well, I took it as an invitation and as soon as it was appropriate I walked back and looked to see if either of the bathroom stalls were unlocked, one was full and locked and the other was obviously occupied but unlocked. I cautiously opened the door and found her waiting there for me, still fully clothed but rubbing her tits, which must have been at least size 38C.

She looked up slowly and said,

“I’ve been waiting for you to come back here”

Me, being as nervous as I had ever been in my life, just said,

“Well here I am, what should we do now?”

She started taking off my shirt and I started unbuttoning hers. As soon as we were both topless I caressed her large tits and she slid a hand in my pants. She felt to see if I was hard or not and her eyes widened and she gasped a bit. Then she took off her pants and mine and while both of us were naked started to blow me. It was easily the best feeling of my life, I didn’t have anyone to compare to at the time but she gave the best head I’ve ever felt, even up to now. After a while I jerked a bit and came in her mouth and she swallowed it all. I usually cum a lot, and on the plane, after having been so horny for so long, my cum almost filled her mouth right up to her cute lips. After she swallowed she looked up and saw that I was still hard. She put her hands up on the wall, turned around and presented her pussy to me and told me to take her hard. Her pussy was perfectly pink and tight and I could tell she was horny as hell because her pussy was so wet, her pussy juices were dripping down the inside of her left leg.

I carefully positioned myself behind her, stroked myself a few times to make sure I was still rock hard, and then put the tip of my 9 inch cock against her pussy. I took a deep breath, reveling in the moment, wanting the moment I lost my virginity to be special. As soon as I plunged into her I could tell this was going to be a fantastic time. Her pussy was so fucking tight most virgins don’t compare to her. It was amazing how intense the feelings were. I could have stood there all day in that cramped room, pushing in and out of her perfect pussy, my cock growing wet with her juices and mine. She came twice, and not too quietly either, before I finally blew my load right into her tight pussy. Her moans were so loud I was sure the passengers in the back of the plane must have heard us. She kept moaning, “Oh fuck me, fuck me hard babe” as I pounded my entire cock in and out of her pussy. As I came, I arched my back, shooting rope after rope of thick cum into her tight pussy. I groaned a bit as I finished orgasming and removed my cock. I watched for a second, mesmerized as my cum began to leak out of her pussy and drip down her leg.

At this point we heard banging on the door and the flight attendant said,

“Sir, you’re going to have to come out now, the fasten seatbelt sign is… oh my god”

She opened the door and saw me, with my cock still hard even after cumming twice. Her eyes widened and she quickly stepped inside the bathroom.

“Sir!” she said, “What do you think you’re doing?! We have strict rules about…”

She gazed at my cock, and trailed off.

“We have strict rules about what passengers may and may not…”

Again, she lost focus as she stared at my still fully erect cock.

“Well! It’s against the rules to do what you’re doing here. If you want me to keep quiet about this you’re going to have to do me too”

She began to strip off her outfit. First the impossibly tight blouse, then the scandalously short skirt, next her hat, then her bra and finally her panties. The flight attendant was about 30 years old and was a total MILF. Her tits were still perky about must’ve measured about 38D bra size. After a few quick strokes to my cock, the flight attendant sat me down on the toilet and began to ride me in the backwards cowgirl position. The other girl got down on her knees and licked my balls while the flight attendant bounced up and down on my cock, her massive tits swinging as she did. The flight attendant came twice before I finally came inside her pussy, my cock still hard and shooting massive loads of cum. I started to put on my clothes when the girl said,

“Wait a second, You’re not leaving here until we both get some anal”

I looked at them shocked at my luck and stammered, “um, yea sure”. By this point I was starting to get soft and both of them got down on their knees and sucked me off until I blew yet another load all over their faces.

They both then got up and put their hands against the wall and stuck their asses out at me. I started with the first girl, since she was so tight and the hotter of the two. I simply couldn’t believe how tight her ass was. I had a bit of a hard time getting my cock in there, but since it was still covered with the girls saliva, I managed to work it in. Then I moved on to the flight attendant, who was significantly looser. I kept going back and forth banging these girl’s asses over and over until I came in each one of their assholes. So now I had cum on them, inside their pussies, and inside their asses. Then without cleaning up any cum from their faces, they put on their clothes and walked out of the bathroom. The flight attendant had a ton of cum on her face and had cum dripping down her leg, which was apparent since she wasn’t wearing panties and only had on her uniform miniskirt. The first girl still had massive amounts of cum on her face and even on her glasses but she didn’t wipe it off, also you could see that her pants were wet from the cum dripping out her pussy and ass. She wasn’t wearing panties anymore or a bra and it was apparent that she had just been fucked, and fucked hard. Once we were all back to our seats the plane landed and everyone got off, except me, the two girls and our lady captain. The flight attendant came up to me and the first girl and said,

“Why don’t you two cum back to the VIP lounge with me and the captain, I’m sure we can have lots of fun together”

To be continued…