Just last night I was sitting at my favorite bar having drinks at my favorite bar having a chat with a guy and now I am getting dressed to the nines for a night he hopefully will never forget.
My hangout gets a lot of locals on Friday nights and there are a lot of city people that come up for the weekend. I usually go there for some drinks and sometimes dinner and listen to the conversations. A guy whom I had never seen there before came in and sat next to me. It turns out he has a second home in the area. He was going through a divorce after finding out his wife had cheated and they had not had sex for sometime. He had hoped to meet some local woman at the bar sometime but pickins are usually slim around here. Any way, he was up to do some work on the house.
The subject of Halloween came up as the date was getting near. Jake as it was, was not a great fan of dressing up. However he had dressed a few times as an officer and as batman. He was a nice looking guy and I was certain he looked good in either outfit.
When asked if I had dressed for the occasion, I tried to blow it off but when pressed I ran through the list of costumes but two in particular I was reluctant to offer up. I told him it was a bit embarrassing and preferred he kept it low key.
God I was nervous but figured what the heck. I explained on both occasions how I'd lost a bet or was drunk and talked into getting dressed as a call girl and the other occasion I went as Elvira.
Needless to say his reaction was shocking. He said he was surprised more so as Elvira. Jake had heard of and had been to parties in which guys dressed as women so that was no shock but for a guy to attempt Elvira, he was impressed.
Jake wanted to know more about my evenings while dressed but I did not feel comfortable being in earshot of people that I knew.
I excused myself while I went to the bath room and when I got back, Jake and my own cocktail were gone. I looked around and found Jake sitting at another location in which we had some more privacy. It looked innocent enough.
After sitting down, Jake was quick to ask more about the two nights. I was able to down play Elvira as I said I pulled it off pretty good but the night was pretty uneventful...the night I dressed as a hooker was a different one.
Of course, Jake wanted to hear all about it.
I began by saying I naturally had help and the outfit was laid out by a lady friend I hung with. I had to admit I was scared because I did look pretty hot. I got lots of compliments and the like.
Jake asked how I was dressed, did guys hit on me and so forth. I did mention how uncomfortable I felt when one guy asked to dance and it happened to be a slow dance. I was a wreck and freaked when the guy tried to press against me and I could feel his boner. Jake laughed.
Jake said he could imagine but he also said how he would have liked to have seen me in the outfit by the way I described it. He also asked if I had any pictures from the night and if I still had the outfits.
Yes I had a pic or two but the clothes were buried somewhere as I never bothered to get rid of them(in actual fact I love dressing but could never come out and admit to it so of course I have that outfit and more!!!)
Moving on, Jake invited me over the following evening on the bases of maybe doing some work for him during the week but insisted I bring whatever pics I had from the night.
Part 2
So here I am, it's now Saturday morning. I am running around locating my outfit from that "night". I have already shaved my body and have putting lotion on to make my skin feeling silky smooth.
My intention is that I plan to go over dressed, stating how I could not find the pics and seeing as how he did want to see how I looked, why not show up dressed?
It was a big gamble. The worst thing is that I embarrass myself or he takes the bait. Seeing as how he had not had sex in a while, he was sort of shopping and if I pull this off, he gets a piece of ass and I get to be with a nice looking man. I too was need of having the pleasure of being with a guy who was horny and I wanted a hard cock in the worst way.
I had some time so I laid everything out. I put no nylons and a garterbelt along with a sheer thong and a lace robe to put me in the mood.
Once the afternoon rolled around I started laying on my beard cover, foundations and such and slowly and carefully applied my makeup.
My eyes I do in a particular way as I have always gotten compliments on how they look, smokey.
Then lipstick, blush, and finally my eyelashes.
Before applying my nails, I finalized my outfit. A tight fitting light gray pencil skirt that fits my bottom nicely. It also shows the outline of my garter belt.
Then I have a V cut top, black that also shows off my defined back as well so there is plenty of skin for him to see.
I also am able to create cleavage that has fooled many a person. The top shows it off quite well.
My hair is a platinum blonde and it does look quite stunning when all put together.
I put on some earrings, rings and a black choker.
While applying my nails, I had a few glasses of wine to take the edge off and to give me the courage to go through with this.
My nails were done and I looked fabulous.
I grabbed my Channel #5 out of my purse, gave myself the once over before I walked out.
It was now or never.
Part 3
It was starting to get dark as I left the house...thank goodness. I walked to my car in my 4" pumps. I love how they feel and they compliment my legs nicely.
Just a 10 minute ride and I would be at Jakes house.
As I pulled into his driveway my heart was pounding. This was my chance and I couldn't back out. I really wanted this.
Turned off the ignition, got out and enjoyed the sound of my heels as I went to the door.
Heart still pounding I knocked on the door.
Waiting there I could hear him approach the door. By now my heart was in my throat.
The door opened.
Jake stood there and his jaw had dropped to the floor...almost. I had better say something quick.
In my best fem voice I could muster on short notice:
"I couldn't find the pics after all so I thought I would try the outfit so could see how I looked"
Jake looked up and down at me as I continued to say: "I can go back and change if this is too much and makes you feel uncomfortable?"
He snapped out of his trance and responded by saying: "Oh my God, I can't believe what I am seeing. I figured you would have looked halfway descent but you looker hotter than my wife. I can't believe it"
Before I could answer he grabbed me by the hand and escorted me in the house, my heels clicking on the tile floors.
He shut the door behind us and I noticed him staring at my cleavage and admiring my long legs encased in stockings.
Now what, I thought.
Jake motioned me ahead of him into the rest of the house, figuring he was probably staring at my bottom. I can walk quite well in heels and sure I put on a good show.
Jake walked me into the living room. It was large and well decorated. Oversized leather coach and a couple of sofas.
He had me sit on the coach and so I sat like a lady, legs crossed as my skirt was somewhat short, showing off my long legs and thighs. If he sat just right, he probably could have looked my thighs to my thong.
Jake asked what I was drinking and I accepted wine.
My host was casually dressed but looked fit and handsome and the more I got turned on, hoping this plan of mine was working. I tried like hell to see if he had a bulge in his pants but tried not to be obvious.
Once my host returned, he made a toast, "To the sexiest woman I have ever laid eyes on".
I must have blushed as he smiled.
I managed a thank you and admitted I felt somewhat awkward. Jake was quite reassuring that my decision to arrive dressed was no mistake and the my presence made his home brighten up.(I was never used to the compliments I would receive dressed as Amber)
As our conversation went on, I felt more comfortable and Jake had more questions about the night I went out dressed up. He was curious as to my reactions to people coming on to me and the guy that tried dancing with me. Let alone having a guy pressing himself against me.
It made me feel nervous and I wound up leaving early.
Jake's response: "If I was there I would have made you feel special. You look so classy yet very sexy. I can't blame those guys for hitting on you".
I smiled and thanked him. Yet again not being able to take a compliment, I changed the subject and asked about his deck.
He held my hand as he helped me up off the couch and escorted me to the French doors leading to the deck. It was lovely and even at night I could see what a lovely view he had.
As I stood by the rail, Jake offered to refill my drink.
It had gotten chilly once darkness set in. I wrapped my arms around my shoulders to keep warm.
Upon Jakes return, he asked if I was O.K. I mentioned how I was chilled, He offered me a sweater but I declined I wanted him to see the whole picture.
After a half hour or so of chatting and warming up to each other, Jake returned with more drinks. I had gotten more chilled. This time, he walked behind me and put his arms around me.
I almost lost it right there.
He apologized for startling me and asked if it was O.K. for him to keep his arms there to warm me up.
I did notice he was careful not to press himself against me but I was quite certain he was smelling my perfume, getting full view of my cleavage and sizing up my neck. WHO wouldn't.
"I am quite comfortable and am certain I am in good hands"
My goodness, was I flirting???? Yup!!
Jake whispered in my ear how hot I looked and how much he wanted to be closer to me (putty in my hands)
I looked up at him and said "thank you, very kind of you to say"
With that, I leaned back and kissed him on the cheek (that took a lot of balls)
Jake looked surprised. When the shock wore off, he looked back down at me. It was one of those moments when you stare at the other person and wonder...what next.
I kissed him on the lips.
It felt like an eternity and it felt so hot.
As we parted lips it made such an erotic sound and I new then this was it. My eyes opened and stared up at him. I apologized and said "I don't know what happened but I couldn't help it. Sorry!"
"Oh no don't be. I enjoyed that very much. I have been wanting to do that all evening. You really don't know how sexy you really are"
"I suppose not but you keep telling me and I am feeling very pretty thanks to you."
I gave him another kiss, only this time I put my one hand behind his head to keep him there as we kissed.
By now I could feel my bottom tingling and noticed I had pre cum oozing out of me.
As we kissed, I slid his hands down to my hips so to give him free rein to see where he would go with it. He was conservative but it did feel nice having him holding me.
We broke off our kiss and I tilted my head giving him access to my neck which he was very aggressive with. My neck is my week spot and he was pressing all the right buttons.
A soft moan escaped my lips. I stepped back into him and there was no mistake. He had a raging hard on.
Jake stopped. I encouraged him to continue but he wanted to apologize, recalling what happened at the Halloween party I mentioned the night before.
"Trust me, hon, it's O.K. I really am ready this time. You feel so hard and it feels so good."
Now he slipped his tongue in my mouth and I was crazy. I turned around so we could be more comfortable as we kissed and I wanted to feel his cock against me. He too moaned as I pressed against his cock.
The kissing was very intense as our tongues intertwined and he would brake to kiss my neck which made me week.
I needed to break off and asked if we could sit on the coach.
We walked into the living room as two lovers would, our arms on each others waist.
As I sat, my skirt rode up my thighs a touch, barely exposing the tops of my nylons, now I didn't care. I looked up and saw the bulge in Jakes pants now.
Once he sat, we started necking, kissing, the works.
Jake commented on how long and shapely my legs were. He also said how much he loved panty hose.
"Have at it", I said
He began running his hand over my legs and it felt electrifying.
We started kissing again. His hands were all over my thighs. I shifted my weight so to expose my bottom in the event he got carried away and felt adventurous.
My breathing got heavy and short and boy was I hot.
As this was going on, I ran my hand across his chest and down to his thighs. I was nervous about going for his crotch but he saved me the worries. He reached for my hand
and guided it towards his crotch.
What a relief. The guess work was over and I was where I wanted to be...at the moment.
I was in my glory and rubbed that cock through his pants. Now I was driving him crazy.
We broke from our kiss. I looked up at him and told him how great it felt feeling how hard he was.
"You are making me feel this hard. You are such a hot and sexy woman and you are turning me on"
Having heard that, I asked him to undo his belt and zipper. He looked at me in disbelief.
I assured him I was ready and really wanted to do this.
"Your cock is so hard and big and I want to see it and stroke it...without pants in the way."
He did as I asked. The excitement was building and he was putty in my hands...or he will be soon!
Jake was about to pull his underwear down. I stopped him.
"Allow me!"
With that I stroked his cock through his underwear as I watched his reaction.
Enough, I slid my hand under the material and felt for the first time, a wet and hard cock.
Once out from under the underwear, I had before me, a huge raging hard on and it was beautiful and I couldn't keep my eyes off it.
My new found lover seemed to be enjoying the moment. I looked up at him only to see he was watching me. He was watching me apparently I was like a kid at Christmas. I kissed him and said: "Your cock is so beautiful and it feels so good. I really want to please you and make you cum". With that said, I leaned over and kissed the tip of his cock. I heard him moan. As I ran my tongue around the tip, he moaned even more. I began to lick up his pre cum and started running my tongue up and down on that massive cock. Then I did all I could and began to swallow that cock. I was nervous and was hoping I was pleasing my lover.
I paused to sit up and asked my lover how that felt. He was on another planet.
"Oh God that feels so good".
"I want you to cum, I want you in my mouth so I can feel you cum. I want to taste you"
Off the couch and on to the floor with me between his legs and began where I left off, my head buried between his legs and started sucking that cock.
It was difficult to decide if I wanted to continue sucking or licking. For me it was a frenzy so I kept sucking and alternated by licking as best I could..
At one point I looked up and pulled Jake down so I could kiss him. It was so hot, knowing I probably had the taste of pre cum and he was kissing me. That kiss felt very erotic.
And by the way I kept stroking that cock the whole time.
Back to sucking and the taste of his pre cum was delicious. I could not get enough and sucked that meat with all I had.
My lover began moaning and I could feel him begin to tense so I figured he was getting close.
I broke off to lick him more and it disturbed him. By the time his eyes focused on me, I went back to sucking. The temptation to climb on top and ride his dick was very great but that was for another day.
As I sucked and licked, his moans got loud and he put his hands on my head. I wanted that load in the worst way.
I looked up at him and said: "I want your load, please cum in my mouth."
Having said that, I sucked again and felt his body tense. Sure enough, he shot load after load in my mouth and the feel of that warm load in my mouth was out of this world. I had all I could do to prevent myself from spilling the load.
I kept my mouth on his cock, moaning myself , getting off on making my lover cum. My own clit was soaked, panties drenched.
Finally I released his cock, licked the sides for a moment before I sat up on the coach, my lover looking spent there on the coach.
He finally opened his eyes and turned to look at me and said: "That was incredible, I have not cum that hard in a long time."
"Well I enjoyed sucking you and perhaps we may be able to get together again. I'd love to suck you off and maybe more". I gave him a nice wet kiss and reached for his balls to squeeze them gently.
"For someone who has never done this, you were really into it and you didn't spill a drop."
"I suppose I am a natural but it was a turn on for me and I enjoyed how you taste. I hope you will consider having me over again soon the next time you are up this way. I could sure use the practice(wink)"
Lover boy kissed me, got up to put his cock away but I had one last feel of it before he put it away.
I went off to the bathroom to fix myself up, hair, makeup and fix my skirt.
Upon my return to the living room, my date had a drink ready for me. I took my drink, told him I did need to leave soon and he seemed disappointed.
I put one arm behind his head, leaned forward to kiss him. I wanted him to think about what happened and to be sure he had no regrets.
"Oh I am sure there are no regrets and you are so hot and sexy and I want to make you feel sexy the next time you come here."
As we walked up to my car, I got him to lean against it and I got right up against him. I placed his hands on my bottom, kissed him and said: "The next time I am here, you can have this(I placed my hands on my bottom)."
He rolled his eyes and shook his head and then looked at me.
"Are you sure?, I mean I wouldn't think you were into that so soon"
"Trust me, I am ready and I want your cock in my ass. I want you to fuck me." I kissed him hard and long to back up my statement. I felt his cock getting hard...again.
I dropped to my knees, pulled out his cock again and started stroking it. As I looked up at him I began talking:
"Do you like the idea of fucking me?"( flicked his cock with my tongue) He replied "yes."
" I want to feel that cock inside my ass, fucking me and making me beg for you to fuck me hard, Will you do that for me?"
He nodded yes.
"For now, I want you to cum again...on my cleavage. I want to feel your hot load on my breasts so I can lick it off my finger as I am driving home. I want to be your cum slut.
He lost it right there, shot his load all over my cleavage.
Watching his sperm shoot all over my chest was intense and I moaned as he covered me in his cream.
That was incredible.
I kissed my lover, thanked him for an unforgettable evening and that I expected to hear from him soon.
We kissed one last time, he patted my ass one last time and helped me in to the car.
I waved and was off.
On my way home, I licked off some of the cum but saved the rest for when I got home when I was going to ride my toy cock and lick off the rest of his load.