This is a true story that happen to me.
I've always loved dressing in women's clothing. I started at the age of 10 with my mother's underwear, then progressed to using makeup and putting on dresses as I got into my teens. I've always had feminine features and was very slim, so when I dressed and looked in the mirror I thought I made a convincing woman. I never went out in public because I never thought I could pass in front of other people so I guess you could call me a "closet queen".
As the years passed, I bought a wig, shoes and perfected my makeup skills to the point where I felt comfortable going out in public, but only at night and only to adult bookstores or adult movie houses where I could get some action. Now at the age of 50 I still look only 30 when dressed and have my feminine manors down to a tee.
I was running low on groceries and had to go to the supermarket, I thought just for the hell of it I'd put on a light application of eye makeup just to make me look a little better. Not enough so you'd notice at a glance, but just enough to make my eyes stand out if you gave them a close look. Once I got to the supermarket I started going up and down the isles picking out the items on my shopping list. I was dressed in a tee shirt and a tight fitting pair of blue jeans that showed off my small tight ass wonderfully. I stopped in front of the cookie section trying to decide which brand I wanted. When I finally decided, I reached for a pack of chocolate chips that looked good and at that same time another hand started reaching for the exact same package I was about to choose. I looked up at this stranger who was about to grab my cookies. It was an older man in his early 60's, very fit and handsome. We both looked at each other laughing because of our error, he looked at me in the eyes, smiled and said "Very nice!"
He said it in such a way that I know he liked what he saw and wanted me to know. We both grabbed a package of cookies and went in opposite directions. In the next isle we met again, he eyed me up and down, smiled and I gave an acknowledging smile. This went on isle after isle. Finally I came to the beer section looking over the range of imported beers. The next thing I heard was "I like Heineken myself". I looked over from where the voice was coming from and it was my supermarket admirer. "I do too" I said as I put two six packs in my trolley. Feeling a strong attraction to this man I said "Well, if you've got the time your welcome to come over to my place and have a cold one". Without hesitation he took a step closer to me and said in a low a sultry voice, " I'd love to." I agreed and we more or less followed each other around the supermarket until it was time to check out.
We were in the same check out line and as he finished paying he pulled his cart to the side and waited for me to pay. When I was done he came up to me, "Hi, my name is Paul". "Hi, I'm Philip nice to meet you". As it happens we were both parked in the same part of the parking lot. "Why don't you follow me, I don't live too far from here" I said, he nodded then got in his car. I only lived three miles down the road and he stuck to me like glue. We pulled into the parking lot of my apartment and Paul helped me get my groceries out of the trunk, gently brushing up against me when he had the chance. As I opened the door to my apartment Paul put his hand gently on my shoulder, I unlocked the door and we went in. "Nice place" he said as we put the groceries on the kitchen counter. "Like a beer Paul"? "Love one". I grabbed two cold beers, popped the top and gave one to Paul. "Let's go in the living room where we can be more comfortable". As Paul took the beer from me he put his hand on my hip, came very close to me while looking me in the eyes and said "Yes, let's get comfortable". Just then I felt my cock getting hard in my jeans, he had a lovely touch and the look in his eyes told me he wanted some fun. As we sat on the couch Paul made sure his leg firmly touched mine, this got me even more excited. Once we had a couple of sips of the beer Paul was now stroking my leg up and down getting me hotter and hotter. I looked over at Paul and said, "If you don't mind I'd like to get dressed up so I feel more comfortable, I think you'll like what you see." Paul squeezed my thigh, leaned forward and gave me a quick kiss on the lips and said, "I'll look forward to it". With that I got up and went into the bedroom to get dressed. Once I was dressed I moved into the bathroom to put on my makeup, this was going to be a day to remember for Paul.
After about 15 minutes I walked into the living room where Paul was enjoying another beer. I was dressed in my favorite shoulder length brunette wig, a white silk top, short black skirt, black garter belt and stockings, black lace thong panties and dark blue bra. To top it off I had on a pair of black 6" platform spike heels. I stood about 8' away from Paul and said, "Well, what do you think"? Paul took one look at me and a huge sexy grin came over his face. "Oh baby, you look hot, come over here and sit down and have a drink". I slowly walked over to the couch swaying my hips as I went. I sat down, crossed my legs and let Paul feast his eyes on me, "You like"? Paul was dumfounded, "God you look so hot". I leaned forward to give him a kiss while at the same time putting my hand in his crotch, rubbing and squeezing it gently while I kissed him gently on the lips. I could feel his semi erect cock through his pants, I squeezed it ever so gently as we kissed. "I like to be called Carol Anne if you don't mind". "No Carol Anne, I don't mind at all".
Our kisses became more passionate while our tongues explored each other's mouths as my hand was massaging his now hard cock over his pants. Paul was running his hands up and down my stocking legs reaching up closer to my panties. "Ohhhh, I think you need to loosen these pants honey, you'll feel more relaxed" I said. Once I said that Paul relaxed and let me undo his belt, then the zipper and finally the snap on his pants. "Stand up baby and let's get these off so you'll be more comfortable". I said. Paul stood up and I slowly eased his pants down to his ankles, his bulging erection was making his underwear stick out like a tent. He slipped out of his pants, then his socks and shoes. Still standing in front of me I began to rub his rock hard cock through his underwear, it was thick, hard and long. With out asking I reached out and began to pull his underwear down, as I did his erect manhood came popping out at me. Paul's cock was at least 9" long. The minute I saw it I grab the shaft and began stroking it up and down, it was the nicest cock I'd seen in ages. "Oh baby, doesn't that feel better"? I asked as I stroked him. Paul grabbed my head as my hand ran up and down his shaft, caressing me while I played with him. I could see some pre-cum at the tip of his cock so I leaned forward and took the head in my mouth swirling my tongue around, licking gingerly around the head. I pulled my mouth off his hard shaft, "Come and sit down baby, have a drink". Paul sat back down on the couch, but now his eager hands were all the way up my skirt rubbing the outside of my lace panties. By this time I was hard as hell and the lace of the panties made his touch even more sensitive on my cock. "Stand up Carol Anne, let me take your skirt off baby"!
Being a good girl I did what I was told, I stood up in front of Paul and let him run his hands up and down my legs, then my ass and then feeling the bulge in my panties. I undid the hook at the back of my skirt to make it easier for him. He reach behind me and unzipped my skirt, it fell to the floor exposing my panties, stockings and garter belt. Paul rubbed the front of my panties slowly and gently. I reached down and grabbed hold of his raging hard on, stoking him slowly with my right hand. Paul could resist no longer, he eased my panties down releasing my now rock hard erection. Without hesitation Paul put my cock to his lips and took me all the way in his mouth, moaning with delight as he sucked my smooth 6". His hands reached back and started fondling my ass as he sucked me, God it felt so good!
I couldn't wait any longer I wanted him! "Come on sweetie, let's go to the bedroom where we can stretch out". Paul pulled away and stood up, I grabbed his hand and guided him into the bedroom. As we walked his hand rubbed my ass getting me more excited every second. Once in the bedroom Paul unbuttoned my top and took it off, he ran his hands over my bra while I stroked his cock and ran my tongue around the outside of his lips. As we climbed into bed and I rolled over to the dresser and got out the jar of anal lube I kept in there. "Lube me up baby" I said to Paul. Handing him the jar I got on my hands and knees offering my smooth tight ass to him. The next thing I felt was the cool rush of anal lube around my asshole being applied by Paul's finger. Deeper and deeper he inserted his finger into my ass, applying more lube while gently finger fucking my ass. His touch felt so good that I lost all control, "Fuck me baby, come on give me your cock" I begged.
On all fours with my ass in front of him, I felt Paul's rock hard cockhead near my asshole pressing gently against it. I relaxed my asshole, reached back and guided him in. He was huge, slowly he eased his big prick in my ass. I was in heaven. I felt the entire head enter me, before I knew it Paul had all of his 8" in me. His cock filled my ass entirely, God it felt so good. I began thrusting back onto his hard member, "Fuck me Paul, fuck me baby" I begged. Paul started fucking me harder, I could feel his balls slapping against mine. "Harder baby, fuck me harder" I cried, his cock felt so good inside me. Suddenly I felt his grip on my hip tighten, I knew he was about to cum, his thrusts were stronger and stronger. "Cum in my mouth Paul, I want to taste you baby". Suddenly Paul pulled his cock out of my ass, "Quick Carol Anne, I'm cumming, suck me now baby"! I quickly turned around and took his cock in my mouth, just in time to feel his hot spurts of cum shoot down the back of my throat. It was much, but I sucked him until there wasn't a drop left.
I kept sucking his big cock when I heard "Now it's your turn baby" at which point he guided my stiff member into his mouth sucking me like I'd never been sucked before. As he sucked me, he finger fucked my ass which made me lose all control, "Oh baby I'm going to cum". Upon hearing this he immediately took me as deep as he could in his mouth while I unloaded my hot load down his throat. Paul sucked me for a good 5 minutes until all I could do was collapse in a heap.
Both of us lying on the bed drained, we reach over to each other, cuddled and kissed. "Carol Anne your fucking fantastic, the best fuck I've had in ages". "So are you Paul, you can fuck me anytime you like baby"!
Paul and I see each other regularly, when he comes over to my apartment I make sure I'm dress when I greet him at the door, we are thinking of having a threesome in the future.
If you liked this story please let me know my Emailing me at LusterXXX@hotmail.com