Hi. My name is Chris, though some know me as Christine. I am John Collins’ mistress. We care deeply for each other. John “keeps” me. He supports me financially and in return it is my pleasure to keep his sex life exciting, as well as entertaining any of his gentleman friends who drop over.
It all began innocently enough, I suppose. I had just turned eighteen and had moved out from my family’s home to be on my own. To support myself I worked as a landscaper, as well as a house painter. I was able to support myself okay in this way, though it required that I budget.
I rented the upper floor in a two-family house out in the sticks. The only other house nearby was one that stood directly behind mine. Otherwise, the area was mostly undeveloped woods. And few cars ever passed on the road, which was a dead end.
It was great being on my own, I was able to come and go and do as I pleased.
One of the really special things about having my own place was that I would take off my clothes whenever I arrived home and wander about the house in the nude. Well, that wasn't exactly accurate, for I had a fetish for women’s clothes and so I would dress up in, say, some silky panties and a sheer blue nightie. I built up a feminine wardrobe. I bought some really nice, sexy lingerie. (I would go to the local department store with a list, and pretend that I was married and was shopping for the wife.) I had very long hair at the time and so had no need for a wig.
There was a gentleman named John Collins who lived in the house behind mine. I met him one day when I was out in the yard tanning. I had on blue jeans that were very tight and were cut very short so you could see the bottom of my buttocks. He came out and saw me and said hello. I walked over to meet him and I could tell I was turning him on.
Well, that evening, at around 10, I raised the blinds on one of my back windows as I was surfing the net. After a while, I noticed my neighbor standing at his back window looking out toward my house. I turned on a red mood light that I had and I thought, “This could be fun.”
With that, I went to my bedroom, put on some makeup, then dressed. I started with some flowery panties, over which I put some black pantyhose. I then put on a Vanity Fair semi-sheer pink nightie and lastly, a necklace and some earrings.
I made my way back to the window; he was still there! I began doing a slow dance.
My neighbor disappeared briefly from his window, and so I paused. But he was back a moment later, and had a pair of binoculars which he peered through toward my window.
“Wonderful!” I thought, and I put some sexy slow jazz on the CD player, then danced back to the window. I gyrated sexily to the music. Soon, I saw that he had unzipped his fly and pulled his cock out, which he then began to stroke. I turned around and lifted my nighty, then pulled the pantyhose and panties down around my thighs. I wiggled and swayed, and pulled the nightie up over my head and off. I turned back around, and my now erect cock was rubbing against the window glass.
I saw him begin to convulse a bit, stroking his cock, and then he came. At the same time, I shot my cum all over the window glass.
This was not the last time I was to entertain him.
A couple of days later, it was a Saturday and quite a hot day. I had made an agreement with my landlord to take care of the lawn in return for a reduction in rent. I put on some lace panties, tight very short jeans, a lace bra and pink halter top. I then slipped on some low-top sneakers. The tenant on the floor below was out of town, as he usually was, on business. So I felt comfortable going out into the backyard in this attire to mow the lawn. I’d also put on some lipstick, eyeliner, and mascara in case my neighbor from the other night’s adventure happened to be around. My hair was tied into two cute little ponytails.
After working on the lawn awhile, John Collins appeared in the yard. I turned off the mower and said, “Hi. What a nice surprise to see you again. I hope you enjoyed the show the other night.”
“Why yes,” he replied. “It was marvelous. A real treat. I’m so lucky having you as a neighbor! Say, I stopped over because I know you do landscaping and I’m looking for someone to care for my yard. Would you be interested? I’d pay quite well. And I’d like you to start right away, today if possible. The grass is getting quite high. Also, I’m having some buddies over for a card game tonight, and I’d like to have the lawn looking half decent. What do you say?”
I asked how much exactly he was willing to pay, and couldn’t believe my ears when he responded. Quite generous! I immediately agreed, and was quite excited since I was hoping to get to know this gentleman better.
We headed over to his place and he got his mower and weedwacker out of the shed. Then he said he was going to mix up some screwdrivers and asked if I’d like one. Of course I said yes.
He disappeared into the house and I started the mower and began working. A short time later he reappeared with a glass and a large shaker containing the cocktails and ice.
“I’ll leave these on the picnic table for you. I’ll be right on the back porch reading, if you need anything.” He had a nice large screened-in porch on the back of the house, and he headed there.
I poured myself a drink. Then I pulled a joint out of my jeans pocket and I called over to him. “Do you smoke weed?” I asked.
“Hell, yes,” he replied. “Come on over here on the porch.”
I headed over and sat on the lounger sofa where he’d settled in. I lit the joint, took a big toke, and passed it to him. This was primo, two-hit Diesel weed. But we passed it back and forth three or four times, and were both getting very buzzed.
He started laughing and asked if I would be able to work between the smoke and the booze. “No problem,” I replied and returned to work. I decided to head out front and knock that off, then finish the back, which was much larger.
After finishing the front and about half the back, the heat was really getting to me, as was the reefer and the booze which I had a couple more glasses of. I looked around. As I said, our two houses were quite isolated and the street rarely saw traffic. So I slipped off the sneakers, then the jeans.
I felt pretty aroused now, knowing he was on the porch reading. Soon he looked up and let out a loud whistle. “Nice!” he shouted. “Feel free to lose the top too!”
I didn’t need much encouragement and slipped off the halter top, leaving me in just bra and panties. I enjoyed the audience and after a while I was done with the lawn.
I returned the mower and weedwacker to the shed and he called to me from the porch, “Come on over here and cool off a bit and relax!”
“Boy, I’m horny,” I remarked when I’d made it inside the porch. “Can you tell?” I teased, knowing full well that my hard-on was protruding from the top of my panties.
“Well, what do you intend to do about it, baby?” John teased me.
In front of where John sat was a wrought-iron coffee table with a glass top. I stood next to the table facing John and started playing with my cock. It wasn’t long before I shot a load onto the glass top of the table. Then I got on my knees next to the table and began licking my cum off the top. I soon licked all of it up, then smiled at John.
“A little protein snack after all that yard work,” I quipped. John let out a howl.
“Listen,” said John as I got up to leave. “I’m having a late night card game tonight starting around midnight. Feel free to stop by and meet my buddies. I’m sure they will all like you, especially if you dress sexy.”
“Okay. Maybe I will. Sounds fun.”
I left John and returned to my place. I made a quick dinner and then decided to drive into town for a few drinks. What I usually did, and indeed what I did that evening, when I was heading out to a new bar, was to dress in bra, panties, a garter belt and stockings, then put a regular men’s shirt and jeans (
tight jeans, I might add) over them. I wore high-heeled men’s dress boots, which were actually unisex. This way, no one would know about my crossdressing, and yet I’d be prepared in case I did meet a sympathetic companion over the course of the evening.
I ended up at a workingman’s bar in town.
It had a pool table; I love playing pool and am quite good at it. I made a few new friends, though none of them seemed to be “my type”, if you know what I mean. But I played a lot of pool, drank a number of screwdrivers, and got a little blitzed.
At last call, at 2:00 a.m., I knew I was in no shape to drive. I got one of my new acquaintances to agree to give me a lift, then told one of the bartenders that I’d be back to pick up my car the following day.
When my new friend dropped me off, I was wondering what John might be up too.
I’d had so much to drink that I staggered back to his backyard, literally zigzagging and seeing double. It was about 2:30 a.m. in the morning. I started getting hard, thinking of John and knowing I could have him whenever I wanted…like right at that moment.
In his backyard, I said what the hell and decided to remove some clothing. It was a beautiful evening, illuminated by the marvelous light of a full moon. Then I stood there wearing the ensemble I’d worn under my regular clothes when I’d gone to the bar: bra, panties, hose and garters. It felt so sexy, out here dressed up like this! I snuck up to the dining room back window and peeked in…why, John and three of his buddies were still playing cards!
I decided to wait a while – I didn’t mind at all. It felt great being outside dressed as a good-time girl. I spotted some birch trees at the back border of the property and I staggered toward them. One of these trees was slanted at an angle. I mounted it briefly and stroked my cock against the smooth bark. Mmm, it felt so good. "What the fuck, I needed a MAN!"
I quickly decided to stagger back to my place for some preparation. I put a nice semi-sheer short nightie over what I was already wearing. Then I sat at my makeup table and did up my makeup: lipstick, eye shadow, fake eyelashes. I put my hair into two ponytails. Lastly, I slipped on some black high heels. That’s better, I thought.
Next, I staggered back towards John’s house and lightly tapped on the window when John finally passed near it. He saw me and immediately smiled a big wide grin. He motioned for me to go around the side of the house, where he opened the basement door to let me in. He gave me a big hug, and squeezed my ass cheeks.
“You’re just in time. Hey, how about coming up and entertaining my buddies?”
I wasn’t sure.
“How ‘bout some coke to get up your courage?”
“Well…”
“Tell you what. Let’s do a few lines and you can decide either way then. Either way will be fine with me.”
God I wanted the blow, I loved the stuff, and what I seem to have put aside for the moment was the knowledge of what a whore I was on coke. I was feeling reckless and great!
He said to grab a couple of cold brews out of the basement fridge while he set up some lines for us. God, after the first line I just realized how sexy I was in my lingerie! After a few more lines I kissed Tom deep and said, “Let’s head upstairs honey. I’m dying to meet your friends.”
“Ladies first,” he said and motioned for me to go ahead. I was soon on all fours trying to negotiate the steps. John laughed. “Here, baby, let me help you,” he said and helped me upright, then I put my arm over his shoulder.
“Say, honey, let me do a few more lines when we get upstairs to get me straight before I meet your friends,” I said.
“No problem, we’ll head for the kitchen, baby,” John replied.
We got to the top of the stairs and he opened the door. Once upstairs, he steered me right to the kitchen. There he set me down on a chair at the kitchen table and sat down next to me. He pulled a tinfoil package out of his pocket, opened it, then got up to get a razor blade.
He returned, sat back down, and began laying out some lines. Such a sweetie, I thought, and reached over to his crotch. I began stroking his cock and leaned over toward him.
“Kiss me, baby,” I sighed. He turned his head toward mine and our lips met, then I stuck my tongue into his waiting mouth. I gave him a deep, wet kiss, at the same time grabbing his cock through his pants and giving it a squeeze.
“God, John, you’re such a great guy… I really dig you, honey.” He returned to cutting the lines while I caressed his hair and nibbled on his ear, then kissed his cheek.
When he’d finished laying out two lines, I got up and sat on his lap. He rolled up a dollar bill and handed it to me. I leaned over the table and snorted the lines. I pinched my nostrils and breathed in deeply. Nice. John then said, “Time to join the others, how about it, honey?”
I giggled and said, “Sounds great to me.” I put my arm around his waist and he held my ass through the nightie, rubbing it softly.
We headed into the dining room, where the card game was. As we entered, one of the gentlemen whistled at me and said, “What have we here?” This, I was soon to find out, was Joe. He looked younger than the other two men seated at the table, I’d guess late forties or early fifties. Very handsome, muscular, with chiseled features, dark hair combed back, his looks definitely aroused me.
“Guys, I’d like to introduce you to my friend Christine,” said John.
Did I fail to mention, I’m very passable as a woman and these men were all taking me in with their eyes, which I loved. “Christine, this is Joe, Ron, and Michael.”
“Hi, guys,” I beamed, not believing my luck being in the company of these four men. Ron and Michael both appeared about John’s age, both handsome enough though not as striking as Joe. It turns out they were married, unlike Joe and John, who were both currently single.
John sat, and I sat on his lap. I was feeling very amorous tonight. I stroked my hand through John’s hair playfully. He turned his head toward me and gave me a kiss on the lips.
The other three looked on with envy. John pulled my nighty up high on my thighs, then rested his hand on the inside of my upper thigh. I knew then that I wasn’t going to be sleeping alone.
We all exchanged small talk as drinks were poured. I told the fellows I was new in town and they in turn told me what a great town it was. “With a great gogo bar,” Joe added. “You know, they’re always looking for new talent…in case you’re looking for a job.”
“Could be,” I responded. “Could be.” Then I looked at John and asked, “What do you think?”
Knowing the truth of who and what I was, John offered, “Worth looking into for sure.” Then he smiled at me and I giggled and gave him a kiss.
Ron piped in, “Well, I don’t know about you guys, but it’s going on 4:00 a.m. and I’m ready to pack it in.” Michael agreed. Joe said nothing, but he really seemed to be staring at me quite a bit.
“Well, listen, guys,” spoke John. “We’ve all consumed quite a bit of booze tonight, not to mention coke. I’d hate to see any of you busted for DUI, so I insist you sleep it off here. The living room couch folds out into a bed, and there are two extra bedrooms upstairs. Help yourself to anything in the kitchen. There are extra towels in the bathroom closet. Sound good?”
They all nodded in agreement.
“Okay, then,” said John. “What do you say we call it a night, beautiful?” he asked me.
“Sure,” I smiled. So saying, we got up and bid them goodnight. We headed out of the dining room, but not before John had raised the back of my night gown and planted his hand firmly on my butt, giving them all a nice view. In the doorway to the dining room, I stopped him momentarily, giving him a really deep and sloppy kiss.
“Okay, Okay, now we’re all getting jealous,” quipped Joe, as we disappeared upstairs.
Once we got into John’s bedroom, I told him I really liked his friends as I disrobed and lay on the bed nude. He said he was glad and that it was obvious they liked me too. Then he undressed and lay on the bed next to me. We necked passionately, then I slid down so his gorgeous cock was in front of my face. I held it and started by gently licking it near the tip. It grew harder and I licked it, sucked it, stroked it. I then stretched out on the bed on my stomach. John rubbed his cock between my ass cheeks. At the same time, I was rubbing my cock against the bed.
Soon, I came onto the sheets. Shortly after, John shot his milky hot load onto my backside. I wiped some of his cum onto my hand and then licked it off. He was enjoying watching me do this, and I was enjoying the fact that I was pleasing him so.
(To Be Continued)