My Surprise

[MrSweerwood]

A regular work night ride on the LIRR turned into the strangest night ever and one I will forever remember.

Long day at work so as always I stop at 7/11 and get a cold Heineken beer. As I know the wait tonight is delayed I grab 2. Finally the train rolls around to Penn station and I get on and assume my normal position. As I sip my beer and the train rolls into Jamaica there she is. The sexiest woman I have ever seen. I tried not to notice her beauty as she looked both ways and chose the 6 seater next to mine. She had 2 pieces of luggage both matching her outfit.

I try to break the ice and said "Normally when I meet a woman with so much baggage she isn't this beautiful "
she cracked a smile as she sat down

odd silence as I try to sit back and not allow her to catch me taking her in

Damn...she caught me staring." I could sure use a drink after the day I had." she said laughing at my beer.

"I have an extra if you like as I would be a fool to say no to a lady"

she smiled slightly and actually accepted.

I introduced myself and ask her where she was headed. She says she is in town for a Trade convention. Sounds good to me I mean I do sales. But she answered pretty vague about the type of sales she did. Said consulting. Whatever.

I have a beer and a pretty lady to talk to for the ride who is going to complain about that?

Finally as we chit chat about nothingness the train rolls into Penn Station. As the doors open I offer to help her upstairs with her bag as the second one looked pretty heavy. We take the esclator upstairs and I help her to the MSG exit.

"If you need help to a cab would be my pleasure"

"Actually Im staying in the hotel across the street The Pennsylvania"

"Oh awesome. Look at th at you get free baggage service , a beer and conversation"

she laughed a little as we stand in front of the revolving doors...

"wish I had a tip to offer you but I dont"

I couldn't help but say "meeting you tonight was all the tip I needed. I was actually going to stop and have one more drink before I head home at the Blarney Stone near here its quite OK. Would have been wrong not to help you. You are too beautiful to carry your own bags "

"You know your a real charmer Shaun. I was actually going up to change before I headed out myself. If you want you can have your drink with me in my room. I have a full bar and I bought my own bottle"

shit who says no to that type of party?

I help her to the elevator and we ride upstairs. I try not to look like I am attracted to her but she catches me checking out her body as I walk behind her.

"you like what you see?"

"I would have to be foolish or blind not too" I say as we laugh walking to her room door.

We enter the room and its a nice size King bed and view of MSG. I place her bag by the dresser next to her carry on she placed down and take a seat.

"Hold on you relax I promised you a drink for your hard work and civility" she says as she cracks a smile. she reached in her bag as she sorts out her clothes to unpack and pulls out a bottle of cognac.

I laugh as she pulls that out and joke. "Trade show business must be tough for you huh?"

We share a chuckle as she explains that sometimes her clients can be a bit too much to bear and she needs to find a way to wind down.

"Well Cognac was definitely what I was going to go drink"

she winks and says "well that cold beer was definitely what I needed so touche'"

Pardon me as I go get ready for the night she said as she poured my glass, turned on the TV to music videos then poured one for herself and slowly disappeared into the bathroom.

I slowly sipped my drink and watched TV as I listened to her start the shower.

After about 25 minutes I hear the water stop and soon after she walks out the door.

She had changed into a nice black dress and walked over to finish her unpacking as she grabbed her shoes and poured us another drink.

We talk a bit longer as she puts on her heels and I cant help take her in.

"Wherever your going tonight I hope they appreciate you and your beauty"

she turns and says they "damn better"

"Most men cant handle a woman like me Shaun. They talk the talk but get scared when its time to man up "

I am feeling this cognac and have no clue what she meant.

"I dont want to hold you up from your preparations as it sounds like you have a tough week ahead of you and who knew trade shows had that much pressure involved? Your too pretty to be stressed."

she smiled as walked over to me in her heels and touches my bald head. I grip her body and rub on her tight ass and told her" Keep fucking with me you will not make your appointment"

she turns around and places her fat ass in my face and I gently bite it as she chuckles and looks at me seductively

"You know something Shaun. I like you . your sincere, handsome and a real gentleman and obviously a freak but I dont want to lead you on. There is something I am not telling you."

Me being a man I ask the usual questions..."What are you married? You have a boyfriend? Your engaged?"

"Ok I am new age...you have a girlfriend?"

she laughs as I ask rapid questions and she smiles then looks so serious.

"I can show you better than I can tell you. Close your eyes ....."

uuuuh ok I say to myself as she slinks her tight fitting dress up above her thighs and I see her panties and the fattest pussy I thought I ever saw in my life

"Ok you have a fat pussy so what?" I say laughing until she pulls her panties to the side and her fat ass dick fell out.
My eyes almost fell out my head

I spit my drink out and tried to play cool but as she pulled her dress back down she walked towards me and I sat there motionless.

"Dont worry honey I am not here to hurt you. Just figured I would let you know what I am so we can have all cards on the table."

As we have been conversing and chilling I felt no ways and although confused I tried to salvage my dignity and told her.

"Listen we met on a humble and I would be a fool to sit here and judge you when I was the one attracted to you. I think that says alot about you looking good and me having good taste "


a smile broke the tension

"Lets have one more drink and we will head out together " she suggests

ok bet

She notices me grow silent and at the same time checking her out and makes her move as I sit by the window.

She walks over and says "Didnt mean to spoil your night playboy lets at least cheers to your good heart and fate for allowing us to meet in my time of need"

I cracked a smile and stood up and lifted my glass. she cheered my with one hand and grabbed my dick with the other.

"Normally a guy may choose to run but you stayed and I respect that. Let me show you what a trade show can get you" she said as she caressed my semi hard dick in my pants . The more I looked in her eyes and at her body I just couldn't resist.

by this 3rd drink I said fuck it as she had my attention from the moment she stepped on the train. I let her undo my belt and pull my already hard dick out my pants. she gripped the base tight and slowly lowered her mouth on my manhood. If I had any reservation about my surprise I sure did fall silent once she slid her mouth up and down my hard shaft. she stopped to look me in my face and talk dirty.....

"I knew you had a big dick the minute I saw you on the train. I saw you checking me out Shaun"

"This is what I need a real mans dick not some sissy trade show man" as she held me firm in her grip and the light from 7th ave shined on her pretty ass face

I tried to play strong but I reach down and grabbed her breast and squeezed them together as she dribbled spit off my cock onto her cleavage.

"mmmmmm look how hard that dick is for me . Let me take my dress off before I mess it up" she said as she unzipped her black dress and let it fall to her heels.

she slowly walked over to the bed and pulled me with her. she turned around as I squeezed her tits and caressed her as I kissed her neck. she laid down on the bed back arched and I kissed the small of her back and slowly traced circles with my tongue around her panty line as I pulled them down,

It was that moment I realized the tip of her pulsating dick poking out the back of her panties. I tried to resist but as I slowly licked her ass hole I said fuck it and me and cognac put that fat dick head in mouth. she gripped my bald head and said "Oh Shaun"

I tried to be quick but the sweet taste of her cock in my mouth made me a little horny and decided to stick my finger in her ass hole as I made my way up to her breast. She squirmed with excitement and I made love to her flesh and nipples. As she took me and inserted my dick in her tight wet ass I could feel my dick get harder . every stroke felt like ecstasy . I pumped her ass until I finally released in ecstasy in her ass hole and we both fell out on the King size mattress exhausted.

As we look at the time and laugh she offers me a washcloth and towel and I jump in the shower to wash off my sweat and lust. As she straggles behind me and does the same. After we dress we both head into the elevator and ride downstairs where I walk her to a cab on 7th ave and she heads to her appointment.

I light a cigarette and decide to go get a beer and literally walk off turned out and thinking about that I just had a sexy bitch dick in my mouth....lol

Funny thing is I was watching pron one day and seen the same sexy bitch online and now I am officially turned the fuck out.

Cant wait for my next surprise

[blackshemalelove]

a well written great story...thanks for sharing.

[jackt]

enjoyed it. first time / surprise stories have a special fell to them. wish I had that experience.