I had met Pete over an on-line dating site, and we had chatted for several weeks and developed a rapport when we decided to have our first real date. We agreed to meet at a local shopping mall parking lot and would do some shopping together.
I spent the morning shaving my body smooth and getting ready. I went with a natural look for my make-up, and peachy pink lipstick. I slipped into a black shape-wear body suit to help with the curves and then slid on some sheer black nylons. I then slid on my black compression slip with the padded bra that finished off my look.
I had a black and white hound’s tooth sheath dress that I had picked out for this day that came to above my knee. It had a thin black belt that helped to accentuate my waist. I put on the dress and then stepped into a pair of tall suede black boots and was ready to go. I grabbed a purse and a light jacket and went to the car.
The drive to the mall went by quick, and the butterflies in my stomach from my nerves had me tingling. I parked at the end where we agreed to meet, and waited for Pete to arrive.
I stepped out of my expedition and straightened my dress while I was waiting, and as I was getting back into my vehicle, Pete pulled up in his blue car. He was a year younger than me, and was very cute. He was shorter than I expected, but just as cute as his pictures. He had a trim but muscular build that showed he cared about his appearance. He was wearing dress pants and an oxford shirt, and looked like any business man out for a casual lunch.
We introduced ourselves and got to eye each other over in the parking lot and both liked what we saw. We walked into the mall and I headed to one of my favorite clothing stores. I had been looking for a skirt suit for a secretary-type look and thought today would be a good day to get one. Pete would look like my boss shopping with me for the day, or at least that is what I hoped for. Pete was very receptive to helping me pick out an outfit, and liked the idea.
We were looking through some racks when the sales girl came over and asked if we needed any help. I told her what I was looking for and that my boss would be helping me make my decision on which one to buy. She gave me a knowing smile and said, "No problem."
I selected three suits; a red, navy, and olive one and she showed me to the changing room, and let Pete sit in one of the chairs right outside the changing rooms. I slid out of my dress and tried the red one on first. It fit very well, as the cut was a style to match my body type well. The skirt was tight, with a small slit and the bottom on the back that made me take smaller steps than normal. I really liked how it felt though, and stepped out to show Pete. He gave a low wolf whistle and the thumbs-up sign, so I knew he liked it.
I stepped back in the booth and changed into the olive suit. It had a longer fuller skirt and a longer jacket, and looked very professional. I stepped out of the changing room and Pete gave me another high sign, but I could tell he liked the first one better.
I looked around and saw that the sales girl was busy helping another group of ladies, so I motioned for Pete to come over and help me. I asked him to come in the room and help with the zipper on the skirt. Pete looked around nervously, but then agreed to do it.
We ducked into the changing room and I kissed Pete fully on the lips. He kissed back, but was holding back for fear of getting caught. I told him not to worry, that other girls did this with their bosses and it was ok. He relaxed and laughed a little and then kissed me again.
I had Pete help me out of the olive suit and his hands roamed over my body while I was grabbing the navy one. I swatted his hands away and told him later. He helped me into the navy skirt and jacket and gave me a huge smile when he saw me in it. I knew he would like it as the skirt was short and showed off my legs.
I opened the door and saw the sales girl was still at the other side of the store. I backed into Pete and started to grind my hips into his groin. He gave a little moan and reached around to massage my chest.
I asked, ”Is this what your secretary normally does for you?”
He muttered an, "Oh yeah," and I knew that this was going to be a good afternoon.
I turned around and gave him a kiss, while fondling him through his pants. He kissed more passionately this time and his hands were wandering over my body. I loved the feeling of his hands on me. I motioned for him to be quiet and dropped to my knees in front of him. I unzipped his pants and fished his cock out from his boxers and gave it a quick lick up and down each side.
He gave a slight whimper and put his hands on my head to continue. I licked it again and then licked all around the head before I stuck his cock in my mouth. It felt spongy, but I did what I liked when my old girlfriends used to give me head.
I sucked up and down and started to massage his balls with my right hand at the same time. He started breathing hard and I could tell he wasn’t going to last very long. All of a sudden he started patting my head and whispered “I’m going to cum.” I sucked him as deep as I could and felt him pulse, and then shoot his load down my throat. I swallowed everything down, and couldn’t believe that my first time happened that quickly.
Pete helped me to my feet and gave me a quick kiss. He straightened himself back up and apologized for coming so quickly. I told him that I was complimented that he came so quickly, that meant that it felt so good for him. I changed back into my original dress and we were stepping out of the changing room as the sales girl was walking over.
Pete got red-faced, but I thanked him for helping me with the stuck zipper on the skirt and gave the clerk a big smile. I told her that I was going to be buying the red one and that my boss was going to buy the navy one for me. I turned and looked at Pete and he gave me a big smile and said yes, he would be glad to. The sales girl leaned in and whispered in my ear that I would need new nylons also, since I now had a run on my left knee.
She winked as she pulled away and pointed to the rack with nylons. I walked over and grabbed a pair of black nylons and turned and pointed to my knee as I walked back to Pete. He made a face as he realized what had happened, and mouthed I’m sorry. I waved him off and told him that it was my pleasure, and that was an occupational hazard from work. He laughed at that and we walked to the register together. I paid for mine first and then went to the changing room to change nylons while he paid for his purchase.
When I came out, he was waiting for me with a smile on his face. He said the sales girl had told him she would be interested in working for him if his company was doing any hiring anytime soon. I thought, you bitch, and then realized that he liked me because I was a special girl with something that she didn’t have.
We walked out of the store and I asked if he would like to go back to my place and get more comfortable. He gave me a huge grin and said absolutely. We walked back to our cars and I gave him a kiss and told him to follow me. He basically tail-gated me the whole way to my apartment and we parked and walked into my building. I unlocked my door and let him into my apartment. He stepped in and I told him to have a seat on the couch while I put away my new clothes. I hung up my new clothes in my closet and came out to the living room to find him sitting naked on my couch.
I said it looks like the party has already started as I pointed to his cock, which was sticking up in the air. He gave me a big smile and said he needed to repay the favor to me and motioned for me to join him on the couch. I walked over and sat down and he began to kiss me very aggressively. He started rubbing his hands over me and began massaging my chest. It felt so good and I let him lead the passion.
He then slid a hand up my leg and underneath my dress. It felt good and he rubbed my thigh. He reached up and started to pull down my nylons, and I lifted my hips to help him out. I stopped and slipped my boots off and then he helped with removing my new nylons, making sure not to ruin this pair. He then slid his hand back up my leg and started massaging my cock through my body suit.
My cock started to get hard with the attention and he slid the body suit to the side so that my cock sprang free. He lifted my hips up again and slid my dress and slip up over my hips so that my cock was free and clear.
He began to lick my shaft and it felt so good. He was kneeling in between my legs as I sat on my couch with my dress bunched at my waist. I began to rub my breasts as Pete was sucking on my cock. He continued to suck on my cock and began to tease my ass with his finger. I let out a gasp as his finger first penetrated my ass, but it felt so good. I whispered to him to keep it up.
He took a quick break from sucking my cock and quickly slid his tongue up and down my ass crack to get it better lubricated. He then went back to sucking my cock and started working one finger into my ass. I began to squirm a little as it felt so good and I told him so. He then pulled his finger out and worked two fingers in at the same time.
I felt very full and told him I was getting closed to cumming. He said good, just enjoy this. He kept working his two fingers around and sucking with his mouth at the same time, and all of a sudden I started spurting cum like a geyser. He tried to swallow it all, but some leaked out at the corner of his mouth. I gasped for air and tried to pull him up so I could like my cum off his face, but he resisted and licked it off his face himself.
He then slid me onto the floor and put a pillow under my hips so they were rotated forward. He crawled between my legs and lifted them up. He slid his cock to the entrance of my ass and started to ease it in. I started to cry out in pain, but then I loosened up and he slid right in. I had never felt so full in all my life, and was amazed that this was how real girls felt when they were getting fucked. He started pumping slowly, and then went faster as I got used to it.
After about ten minutes of this, he tightened up and came right in my ass. I had gotten hard again, and as he came in my ass, I shot a small load all over my chest again. I was amazed that I could cum without even being touched, but it was so enjoyable.
If all my other first dates went this well, I would be a lucky girl.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com
with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/my-first-date-1.aspx">My First Date</a>