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Ashley’s First Time With a Guy

Ashley’s First Time With a Guy

DISCLAIMER: Story is merely fantasy and completely fictional. So please do not believe this happened to me or ask me questions about it, thinking it is true. I am writing simply because it is a fantasy and it’s just more fun that way;)

So it all started on Valentine’s Day of that year. My wife and I had gone to dinner and got a hotel room for a romantic evening. And of course being the fun loving couple we are, we had a couple bottles of wine at dinner and decided to head to a bar for a few more drinks and some dancing after dinner. So by the time we were heading back to the hotel we were pretty drunk and having a lot of fun.

I, of course, had set the mood in the room earlier in the day when I had stopped by to check us in so we wouldn’t have to deal with it later. I sprinkled rose petals on the floor leading from the door to the bed, set up some white xmas lights in lieu of candles (due to them being banned in hotels), arranged for champagne on ice and chocolate covered strawberries to be brought in prior to our arrival, and had a couple gift bags on the bed with some sexy lingerie in them.

As we enter the room she is completely swept off her feet by the romantic scene in front of her. She was very excited by the gifts, so I told her she should open them while we enjoy our champagne and strawberries. More than agreeable to it, she slinked her sexy body over to the bed, sat down and began removing the items from the bags as I brought the drinks and tray of strawberries over. Apparently I have very good taste in lingerie because she insisted on trying it all on immediately. So she disappeared into the bathroom as I put on some music and enjoyed my champagne.

She must have tried it all on because it took a while, but eventually I heard the door open. I was told I found the most perfect stuff, but she found the particular combo for the evening. She came out wearing a black bra and panty set with little hot pink details, black thigh highs with little hot pink bows at the top, and black stripper platforms which she had packed in her bag from home.

Now you have to understand, she has an unbelievable body… 5’5”, 100lbs, not an ounce of fat, A cup tits but perfectly proportioned to her supermodelesque frame, and an ass that could end wars… So even though it sounds like a simple set she came out in, it was still jaw dropping on her.

After seeing my face and expressing her gratitude, she said she felt bad that I did all that prep work and got her nice gifts, but she didn’t really have anything for me. So, jokingly (even though it was a fantasy of mine and I did it without her knowing), I said that they really didn’t make any sexy little things like that for me anyway.

Then I saw her have a thought. She told me to wait right there and disappeared back into the bathroom. After a few minutes she emerged empty handed and told me my surprise was waiting in the bathroom. As I got up she coyly smiled and strutted to the bed taking a seat and sipping her champagne.

Upon entering the bathroom, I found the toilet seat down and a sheer black thong sitting on it with a note next to it saying, “wear me”. I recognized it, this thong was a part of another set I had given her, but it was one of those one size elastic band type so she knew it would stretch enough to fit.

I had been wearing panties for a while without her knowledge and it had always been a fantasy of mine to wear them for her. So when I saw this, my cock nearly sprang out of my pants. Just as I started to undress to follow her command, I heard from the bed, “I’m waiting...” I quickened my pace and as soon as I pulled that soft, sexy material against my rock hard cock, I nearly finished right there. It felt so sexy.

I emerged to a big smile on her face asking what she though, posing a little of course. She said they were perfect and that I was right about sexy things not being made for me, but she was willing to share. Also noting that my rock hard cock oozing with precum proved how much I was enjoying it. We immediately proceeded to have one of the hottest nights of our lives.

A couple days later I was still smiling about it, thinking she had no idea how much I loved it and it probably wouldn’t happen again. But as I returned home from work, there was a gift bag and card sitting in the hallway with my name on it. It was a Valentine’s Day card. The inside read “Sorry it is late, but this should get you started… Happy V-Day Sexy!”. Opening the bag, I found three pairs of panties in different styles and colors, as well as a $50 gift card to Victoria’s Secret. It was one of the greatest days of my life.

Over the following months, my collection grew. And not just panties, but all sorts of lingerie, even some heels. My wife even started introducing me to her toys. She started slow with some of her smaller dildos and vibrators, but we eventually graduated to using double sided dildos together. A whole new world was opening for us sexually.

As October rolled around, the Halloween party invitations started rolling in. We had decided to dress as a couple and go as the couple from the movie “300”. Most of the parties were mutual friends of ours, and there were a couple invites from some coworkers we hadn’t been around much as a couple.

At some point during the week leading up to all these parties we were lying in bed, I also happened to be wearing some of my lingerie, when my wife seemed restless. I asked what was going on and she said she wanted to try something new, but wasn’t sure how to ask. So, excited by the prospect of something new, I told her to just ask. Then she began:

“Well, I’ve been thinking about Tom from work’s Halloween party, and I want us to wear a different costume to it…”

“What do you want to do?” I replied.

“Ummm… you really have only met a couple people from my work, and really only in passing… Soooo I was thinking maybe we could go as girlfriends? I mean you would not be dressing up as a girl for your costume. You would pretend to be a girl in a girl’s costume. I would introduce you as my friend Ashley. I would of course let people know that you were at one of your coworker’s parties and we couldn’t make both.”

“You think this would actually work? I mean here at home is one thing, but it could be really embarrassing if we get caught…”

“Let me worry about that. I’ll have you passable in no time. We’re already shaving you’re body hair for you’re other costume anyway.”


I had never thought about dressing outside, much less in front of a bunch of people I may bump into again. I was terrified, but strangely excited as well.

My wife had lived up to her word. She bought us some sexy costumes, She was sexy Snow White and I was sexy Dorothy from “Wizard of Oz”. She also bought me a real looking wig as well. When I looked in that mirror after being dressed, wearing the wig, and having my make up done… I wanted to fuck myself! I was hot! And as always she was looking gorgeous. We looked like absolute sluts, our little costumes barely covering our sweet asses and the cleavage on her as well as the cleavage she created on me.

We ended up taking a cab to the party because I knew it was going to take more than a few drinks to calm my nerves. And almost immediately as we got in the cab, the driver started hitting on us. My wife of course did all the talking as I was very unsure of my female voice. But wow was this guy into us. And maybe it was to break the nervousness for me, or maybe just for the thrill, but as my wife paid upon our arrival, she whispered something to the driver.

I was standing outside the cab right next to the driver side door staring at the house trying to figure out how I was going to fool everyone. Then my wife came around in front of me pulled me close and kissed me. But while she was kissing me, I felt her hands wander to my ass and in an instant, she pulled up the back of my skirt (not that there was much to pull up) revealing my ass cheeks separated by my cute little white thong. I couldn’t help it, I just let it happen. He beeped and drove off, she looked at me and said, “See you’ll be fine.” Now I was excited.

We fixed our make up after our little show for the cab driver and headed in. She went in first greeting people with hugs and introducing me as her friend from college just in for the weekend. Thankfully the music was loud enough that I could keep my voice low and sound somewhat feminine. After she said hi to everyone, we grabbed a couple drinks. Apparently people had been there for a while because they were pretty drunk already, which made me feel a little more confident. After a couple drinks and conversation, in which I contributed very little, my wife suggested we dance a little.

As we made our way to the middle of the dance floor, she whispered in my ear that I must be really hot because there are a lot of guys checking me out. Unexpectedly I felt sexy from that comment and my tightly secured cock lurched a little. Never thought about guys before, and now I’m exited about them checking me out…?

“Remember, you’re my friend from college, not a guy trying to get laid. You have to dance like it.” I think she noticed my confused look.

“You have to dance sexy, show off a little for the guys. Dance they way you like to see girls dance… oh, and of course lets give them hot little show…”

I was a little slow at first, but really started to feel sexy and get into it. We just started putting on an absolute slut show. Dancing and touching each other. It seemed like we were out there for a while. Then all of a sudden, I felt a body behind me. I almost froze, I looked at my wife still dancing in front of me being watched by a few horny guys around us. She saw my surprise, looked me in the eyes, winked and smiled. I turned my head and saw it was her friend Tom behind me! With that encouragement from my wife, I backed into him a little closer.

Before I knew it, I was grinding my cute little slut ass right against him. I soon found out exactly how much he was enjoying it, I could feel his rock hard cock right through his costume pants, it was huge, and with my tiny skirt he was basically grinding that monster right against my tight whole. I began having my own problems containing my “excitement”. He got bolder with every song, his hands began to wander, I was worried he might find my “secret”, but I was just too excited at this point and was helpless to stop him. Tom moved his powerful hands under my short little skirt, feeling my hips as I worked my ass over his bulging cock. I felt so sexy as he moved them around to my inner thighs, even brushing against my “clit” a couple times… it was hot!

After a few more songs, my wife and I excused ourselves to the ladies room. The door wasn’t even closed before she was kissing me deeply. We made out for a couple minutes until she broke it off…

“Those guys want you so bad! Tom especially.”

“I know.” It was all I could muster, my head still spinning.

“Well what are you gonna do?”

“What do you mean?” I’m lost.

“The party is starting to thin out…”

“So… We’re leaving soon?” Still completely lost.

“Look, I saw how much you enjoyed the attention. I also couldn’t help but notice you enjoyed riding on Tom’s cock while dancing and getting felt up…”

“Uh… but…”

“No need to explain to me Ashley, you’re a hot single chick, you should enjoy yourself. I have to go home soon and wait for my husband to get home from his party.”

I was stunned. She gave me another kiss, reached under my skirt, giggled and said “Oh yeah, you’re into it…” She walked down the hallway, looked into Tom’s room, looked back and said “See you at the house Ash”

I walked down the hall, looked into Tom’s room, and he was catching some sports news on TV. He saw me and called me in to see something. I sat next to him on the bed and watched an incredible football highlight. But when I looked over to him he just leaned over and brought me in for a deep kiss.

I had no idea what to do, I can’t get caught like this. I gave in and began kissing him back. His tongue darting in and out of my mouth, I got caught in the moment and was overcome by sexual desire. He was feeling me all over as I began to stroke him through his pants. He was bigger than me and I was kind of excited to see it, Just then he started to run his hand up my thigh and I realized he was about to get a handful of surprise… I had to think quick.

I dropped to my knees, unzipped his pants, and springing free his 8 inch cock. I was in awe, this was the closest I’ve ever been to another man’s cock, and I was stroking it. I now knew what I had to do, he just verbalized it..

“Suck it for me Ash, I want your mouth on me so bad…”

I lowered my face to him, beginning at his balls, I ran my tongue slowly and deliberately all the way up the underside of his thick shaft and circling the head with my tongue a couple times before plunging my mouth down on his erect throbbing member. I head him groan and lay back on the bed. I started slow, exploring as much of his rod as I could. I loved hearing his low moans as I slowly worked my mouth up and down him devouring him like an absolute slut. Along with his groans, he told me how he had been in love with me ever since I walked through the door. He loved my body, my dancing, and just how hot of a chick I am.

As I quickened my pace, I could sense him getting close by his breathing and moaning. And with a grunt, he completely filled my mouth and throat. I’d like to say I took it all down, but it was a lot and it was my first. I dribbled a little, it ran down his cock to his balls. Wanting every last drop I pushed his now limp cock aside and began licking it off his balls, and by the time I made my way to his cock, he was erect again!

He looked at me and said, “That was amazing, I’ve never cum like that before. I want to fuck you so bad right now.”

Once again thinking quick I replied “Not to gross you out stud, but I’m kinds on my period. but you can fuck my ass if you want? You just have to promise to be gentle and let me be on top because you’re hung and I don’t usually do this.”

Of course he replied with an enthusiastic, “Yes”.

I don’t know what got into me, but all of a sudden I’m fearless and about to get fucked in my virgin ass by my wife’s coworker. As he continued to lay back on the bed, I climbed up and hovered myself over him in the reverse cowgirl position. Trying to ignore my own raging hard on I have taped against myself, I pull that little white thong aside revealing my tight puckered butt hole. He told me how gorgeous it was as I lowered it to meet the head cock, well lubed from a combination of my saliva, some of his cum I missed, and he now fresh stream of precum. My heart was nearly beating out of my chest as I lowered slowly onto him, feeling every thick inch stretch me out, I close my eyes let out a moan.

As I open my eyes I see my wife standing in the doorway which we seemed to have left open, she just smiled, winked, held up a piece of paper that said, “C U AT HOME”, blew me a kiss and disappeared. I just continued to ride Tom up and down his thick shaft. It felt so good deep inside me. I just closed my eyes and started rolling my hips which started running his cock directly into my prostate, the sensation only made me want it more, I was fucking him for all I was worth, as our moans grew together.

When I open my eyes again, in the STILL open doorway, is one of their other coworkers who I was introduced to earlier in the night but forgot his name. He had is cock out and was stroking it while watching me fuck Tom. I couldn’t take it, so I waved him in. He undressed the rest of the way, walked over and I took his average sized cock into my mouth with ease.

I felt Tom begin to get up. Tom and his random coworker put me on all fours going across the bed, one of them at each end. I began sucking again as Tom plowed me from behind, he was nailing my P-spot, I knew I wasn’t going to last long. Thankfully his pace began to quicken, I could tell he was ready to cum again. Just the though of having him dump his seed in my ass was enough to send me over the edge. He hit my prostate again and I tensed up as I shot load after load into my panty, thankfully it was cotton and caught it all.

Tom felt my muscles tighten around him and it was too much, he dumped his second load in me as my muscles were tensing from my own orgasm. He finished quick and told the other guy he had to try my ass while I clean Tom off,

“I just made her cum from fucking her ass”.

So they switched ends and it did not take long, being smaller than Tom the other guy slid right in and pounded my sweet ass for all he was worth as I cleaned Tom off. His pace was too much and I came again, once again squeezing him and forcing him to dump his load in me.

I stood up, straightened my thong, gave them both a deep kiss, and thanked them for the fun. I awkwardly made my way through the party, makeup I’m sure all messed up, probably walking a little funny from the pounding I just submitted to, went out front and grabbed a cab home.

My wife was in bed waiting for me and asked if I had fun. I told her she wouldn’t believe me if I told her how much fun I had and how much I loved her for it. I told her everything that happened, then we fucked passionately, then went to bed.

To this day, Tom is always asking my wife how Ashley is doing and if she’s coming to visit again soon. She might have to. ;)

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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