This story is geared toward bi-sexual, bi-curious, or open minded men. It is about a man with a panty fetish who re-unites with a female childhood friend who ends up dominating him. In the story he experiments with cross dressing, panty sniffing and anal sex. Parts of the story are true and have happened to me. Parts of the flashback to his childhood are something that happened between me and another girl when we were that age. And the part about His wives best friend letting him see up her skirt also happened to me.
My wife and I had been married for over a decade; we were in our mid to late thirties and had two wonderful kids. As with most marriages we had our ups and downs but generally we got along. Our sex life though had begun to taper. Instead of sex I found myself masturbating to porn mags, or web porn, and occasionally slipping on some of my wife Jessica’s undergarments. I wasn’t gay or bi, but I did like women’s panties, a little too much. I had never cheated on my wife and never really planned to, until Maria came along.

My schedule for the past few months had been busy, I was working 10 or 12 hour days, and not seeing much of my wife and the kids. I finally had begun to catch up at work and was enjoying one of the first dinners with my family in a long time. My wife had been talking about her new co-worker, whom she shared an office with. Apparently they had become quite close and Jessica had begun to spend time with her outside of work. When Jessica told me her name was Maria I almost choked. Springville was a big town, but was by no means a city. I wondered what the odds were that it was the Maria I had once known. I asked my wife what her last name was and sure enough it was her. My mind began to run wild with long forgotten memories.

When I was a boy we lived in Sunny Glave, the next town over from Springville, and Maria had been my neighbor. We lost contact when I was 12 because I had moved to Springville. Maria was a couple of years younger than me so we were by no means friends, but on an occasion we would play together. I had always had kind of a crush on her. She was by far the cutest girl in the neighborhood. She had big brown eyes and long straight brown hair and the happiest of smiles. Maria was also the first girl I ever saw naked. We sometimes played doctor. A few months before I moved Maria and I were walking in the woods behind the neighborhood. I was a hot day and neither of us had brought a bathing suit. We walked for a mile or so and came to a small swimming spot in the stream that ran through the woods. She complained of being hot, so I suggested we go for a “skinny dip”. Maria without reluctance agreed. Soon we were stripped down to out undies. It had been about a year since I had seen her naked, and I was much more curious about girls after two weeks earlier seeing my first nude magazine. She had removed her t-shirt revealing her flat chest with two pointy nipples. Her underwear was pink and had some cartoon on it. I laughed at it, teasing her about her undies. I pulled off my briefs, and tossed them aside, I already was half erect, my penis sticking straight out. Maria instantly commented on my newly grown pubic hair. “Ewww, yuck, you have hair down their now..” she exclaimed. She then pulled off her panties and tossed them at me. I batted them aside and laughed, staring at the cute little bald cleft between her legs. “I want to try yours on.” she said and then she ran over and picked up my white briefs and slipped them on. She joked around in them for a while, spoofing me. Then she asked me to put on hers. I told her that I wouldn’t, but she kept begging. She promised not to tell anyone, so finally I did.

I picked up her little pink panties, looked around to make sure no one was watching then slipped them on. They felt funny and my balls were hanging out of them. We laughed more and soon we were both naked again and swimming. Maria and I swam for a bit, both taking time to admire each other’s body. As we both got out of the stream to leave I noticed her nipples were puffy and erect. I asked why, she shrugged. Then she giggled and pointed out my fully erect penis. She then asked if she could watch me pee. I obliged and started pissing while erect, shooting a great ark of piss up into the air. We laughed together. I asked her if I could watch her and she squatted and pissed right in front of me. After that she asked me if she could touch my dick. We had done this before, the last time we were naked together. She grasped my then 5 inch penis. She played with it for a minute or two, not jerking me off, but just fondling. While she did that I returned the favor and placed my hand between her legs and fondling her mound. We giggled together, than I asked her to put my penis into her mouth. She hesitated, and I re-assured her it was alright by kneeling down and kissing her pussy. She giggled when I did. I stood up and then she knelt and kissed my dick, she even at one point put it into her mouth. I remember it being the best feeling I had ever had at that point. After she stopped I knelt again and kissed her crotch a few more times. I don’t know why but for some reason I felt like playing a joke on her, so I slid my finger into her butthole. She cried out and hit me. I apologized but Maria was upset and she got dressed and left. That was the last time I spoke to Maria.

Knowing my wife now knew her I felt really uncomfortable. I almost blushed when my wife spoke her name. I couldn’t deny knowing her I just hoped she had forgotten what happened and most of all that she didn’t tell my wife.

“Why, do you know her?” Jessica asked me.

“Uhhh, ya, actually. She used to live down the street from me when I was a kid and lived in Sunny Glave. I didn’t know her too well, but I saw her around the neighborhood.” I replied.

Jessica almost dropped her fork. “I can’t believe it!” She laughed, “You grew up next door to her! Wait until I tell her tomorrow. That is so funny.”

“I wouldn’t say right next to her.” I replied, “She might not even remember me.” I hoped she didn’t remember me at least. Or did I? I started thinking about what she might look like, about her putting my dick in her mouth…

About a week later my wife invited Maria over for dinner. The kids were at their grandparents for the night. I was nervous as hell, but also curious to see what Maria looked like as an adult. I didn’t get my hopes up, because I knew plenty of hot girls in high school that didn’t turn out that hot as adults. When the door bell rang my wife and I both went to greet Maria. The door opened and my heart almost stopped. In walked a beautiful woman, about 5’ 9”, with long brown hair, wearing a white blouse and a short skirt. She was not skinny, but not fat either, she had an hourglass like figure, curvy hips, a slim waste, and easily D-cup breasts with a lot of cleavage showing off. He cheeks had gotten plumper, but her smile hadn’t changed. She looked at me first, with her beautiful brown eyes, and smiled.

“Hi, Steve, it’s been quite a while hasn’t it.” Maria said as she walked up to me and gave me a tight hug, squishing her large breasts against my chest. She kissed my cheek and then hugged my wife.

“I haven’t seen you blush like that in five years.” My wife said. They both laughed, I laughed along nervously, and then we went into the living room and sat down. My wife went into the kitchen to finish serving dinner and Maria and I reminisced about our childhood in Sunny Glave. Neither of us mentioned our sexual escapades. I kept trying to tell myself that she had forgotten, but I knew she couldn’t have.

Soon my wife called us into the dining room to eat. During dinner we discussed a variety of topics, laughing and getting to know each other. We all were drinking wine, and quite a bit of it. Maria asked us if we could pet sit her Chiwawa next week when she was out of town. We told her we would be happy to. Thoughts of raiding her panty drawer flooded my mind. As it got later Maria occasionally snuck in a glance at me, I could tell she was trying to do it discretely so my wife would not notice. When our eyes would meet I could feel the sexual energy. I asked myself if it was just me imagining things. Finally my wife got up and went to the bathroom. Maria was sitting across from me. She sighed and took off her heels. Our eyes met again.

“Do you remember the fun times we used to have in the woods together?” She asked quietly. My jaw almost hit the floor, I was unable to respond. Then I felt her foot touch mine. She gave me a devilish smile that I hadn’t seen in over twenty years. Her foot then started climbing up my leg. “I think about those times often when I masturbate.” She then licked her upper lip in a sexy fashion. By now her foot was resting in my crotch, she gently moved it up and down. My cock was already hard. “Do you think of me when you masturbate?” She asked.

“I will be the next time I do.” I responded. I grasped her foot and caressed it. She moaned in response. We heard my wife coming out of the bathroom. Maria placed her foot back on the floor and we both tried to regain our composure. After another fifteen minutes I suggested that we move into the living room. Jessica and I sat together on the couch and Maria sat across from us. We continued drinking and talking. My wife and Maria stated talking about work. I began to zone out, trying to fathom what just happened at the dinner table. After a while my wife went into the kitchen to get another bottle of wine. As soon as she left the room Maria placed her foot up on the couch and started picking at a toenail. I glanced over at her and could see right up her short skirt. She wasn’t wearing any underwear. Her pussy looked like it had been shaved about a week or two ago. I could see her pubic hair was starting to grow back, but it was still short. Her pussy lips were plump and they had a beautiful shape to them. Her clit was larger than I remember; it poked out from between her lips. Maria never looked over at me as she showed me her pussy. My wife came back in with a fresh bottle of wine. Maria crossed her legs again. My wife poured us all a glass, and I immediately chugged mine. My wife looked at me wide eyed and laughed.

“What was that all about?” she asked me.

“I am just thirsty.” I told her and we all laughed.

An hour later Maria left, again giving me a tight hug before she departed. My wife thought nothing of it. My wife and I got ready for bed. I could not believe how horny I was. As we settled into bed I began to flirt with Jessica. She ignored my advances and finally asked me to stop. She said she was too tired. I tried to coerce her by saying this might be our only chance for a while that we would have some alone time with no kids. She still wasn’t interested. After she fell asleep I got up and went into the living room. I brought some napkins and sat down on the couch. I thought about the night and soon had a raging hard on. I dropped my boxers and jerked off. I thought about Maria’s exhibitionism, her foot on my crotch and her sexy glances, her firm breast pressed against my chest. I also thought of our times in the woods, fulfilling my promise I made to her earlier. I wondered if she was doing the same thing right now. I eventually came, shooting the most cum I had shot in a long time.

The next time I saw Maria was Tuesday, the day she was leaving town. Jessica and I went over to her place so she could give us instructions on pet sitting. She told us to make ourselves at home and that she would be back Saturday morning. My wife said she would visit before she went to work, I volunteered to cover nights. She showed us where everything was and we spent some time together getting to know the dog.

Maria left town and I went over to her place Wednesday night. I fed and walked the dog. After I got back from walking the dog and I knew I had to snoop around. I went upstairs and poked around her bathroom, looking through her amenities, smelling her lotions and shampoos. My next stop was of course her bedroom. I had been dreaming about this for two weeks. I noticed she had left her middle dresser drawer open a couple of inches, I could see panties in the drawer. I opened it the rest of the way. My dick began getting hard as I sifted through her underwear. Thongs, lace panties, silk panties. Touched them and rubbed some of them on my cock. Under all of the garments I felt something big. I moved all of the panties to the side to reveal a couple of vibrators and a strap-on dildo and some lubrication. I could not believe what I was seeing. Under them was a couple of porn mags, both of them were about women fucking men in the ass with strap-ons. My cock was now so hard it felt like it was ready to explode. I pulled out one of the mags and noticed that it was this month’s issue. I knew that Maria was leaving a message, and I like it. The next thing I saw blew my mind, between the mags Maria had left a pair of panties, they were pink with cartoons on them, and they were the same ones she made me wear in the woods when we were kids! I needed to cum, and needed to cum soon. But first I wanted to see if she had left me any surprises in the hamper.

I looked into the hamper and pulled out some cloths to find not one, but five pairs of dirty panties. I pulled them out and sniffed them. I could smell the musky scent of her pussy juices. I put one of the pairs on, my hard cock hanging out the side of them. I opened the first magazine and noticed she had written 3 page numbers in the first page. I went to the first page she had written down. On the page she had written “Wednesday” and circled a picture of a woman putting a small butt plug up a man’s ass. Kinky I thought. I went back over to the panty drawer and pulled out a small butt plug and the lubrication. I lubed the plug up and slid it into my ass. It felt awkward and hurt a little as I slid it up my ass. Then when it was almost all the way in it popped into position as my ass clenched around it. I turned on it’s vibrator and was amazed at how good it felt. I had never felt anything like it. I pulled the panties back up over it and pulled my cock out of one side. I grabbed the little girl panties she had left for me and began jerking off. Before too long I began to climax, shooting cum into the pink little girl panties. It was by far the best orgasm I had ever had in my life. I cleaned up and put everything away so my wife wouldn’t find out.

The next night I did the same thing, I turned to the page marked “Thursday”, this time the page she had left for me showed the guy fucking his ass with a vibrator. He was wearing a pair of thigh highs and a garter belt. He also had a bra on. I dressed accordingly, stuffing the bra with socks so it looked right, it felt sexy. I looked at myself in the mirror, it turned me on to see myself dressed up in Maria’s lingerie. I didn’t have any panties on, because the man in the picture didn’t. I lubricated up the vibrator that looked similar to the one in the picture. I was cock shaped, and smaller than my cock, but wider than the butt plug. I knelt over the end of Maria’s bed and started to put the plastic cock in my ass. I slid the head of it in and had to stop for a minute because it hurt. After a minute I felt my asshole relax a bit and I continued to slide it into me. This dildo was longer than the butt plug. Once it was all the way in I took another break. I turned on it’s vibrator and relaxed as it pleasured my insides. My legs began to feel weak with pleasure. I sniffed a pair of Maria’s dirty panties and wondered if she was thinking about me. I then began to slide the dildo in and out of my ass, slowly at first then faster. It felt sooo good, it was a whole new sensation. I stood up and went over to the mirror and started fucking my ass with the dildo. This time I fucked my ass at the pace a man fucks. My cock was hard and it was dripping clear pre-cum. I continued ramming my ass with the plastic cock for about ten minutes. I felt an orgasm coming on and I hadn’t even been stroking my cock. I started jerking off, and within seconds I began to cum, again I came into the same pair of little pink panties.

On Friday I went over to Maria’s. I walked the dog and fed him. Then I went right up to her bedroom. Friday’s porn picture showed a man wearing a thong, thigh high fishnet stockings with a garter belt, and a stuffed bra and a teddy. In the picture he was getting his ass fucked by a woman wearing a strap-on. I dressed up in all the lingerie and again looked at myself in the mirror. I pulled out the lubrication, the strap-on and her little pink panties. I looked at the strap-on, it was bigger than my cock, both longer and wider. I wasn’t sure if I wanted to stick it up my ass, then I thought of Maria wanting me to.

I was just about to lubricate it when I heard the door downstairs open. Maria called out, “Hello, anyone home? Steve are you here?” I contemplated running into the upstairs bathroom, but I know she wanted to find me like this. I sat on the edge of her bed. She came right upstairs and entered the room. She smiled. “I was hoping you would get my instructions.” She said with a sinful smile. “You see, ever since seeing you in my panties when we were kids I’ve kind of had this thing for men wearing women’s undergarments.” She walked over to me. She looked at my erect 8 inch cock hanging out of the side of the panties, “You’re cock is much bigger now.” She remarked. I stood up. She then grabbed my ass and pulled me towards her. She whispered into my ear, “I have been waiting to get you back for ramming your finger in my tight little girl ass.” She then started licking my ear. We began to kiss passionately. While we kissed she took off her skirt and blouse. I undid her bra and threw it aside and began caressing her firm breasts. Her tits had hardly any sag to them, she had huge areola, with nipples that stuck out at least a half an inch. I pinched them and soon her nipples were erect. She forcibly pushed me onto the bed. She removed her panties and threw them at my face.

“I have been wearing them all week for you.” She said. I sniffed them and they smelt rich with her pussy juices. I looked at her pussy. She had just shaved it, it was totally bald. She saw me looking at it and said, “You like my bald pussy? I shaved it this morning for you, I thought it might bring back some childhood memories.” She began to put the strap-on on. She told me to lie on my back. I did as she commanded. The whole time I could not believe this was happening. After she had gotten the strap-on on, she lubricated it and came over to the edge of the bed. She placed my fishnet covered legs up in the air and rested them on her shoulders. She put some lube on her index finger and pulled the thong I was wearing off to the side, exposing my asshole. She rubbed my asshole with her finger for a minute or two, it seemed like an eternity and it felt great. All of a sudden she jammed it into my rectum, I moaned in response. “I have been waiting over twenty years to do that.” She then began to finger fuck my ass. I reached down to start stroking my cock, I pulled it out of the side of the thong and then Maria slapped my face. It totally caught me by surprise. “That is off limits, don’t touch it again, it is mine to play with.”

Next she pulled her finger out of my asshole and stroked the huge Strap-on. She smiled at me and positioned it’s head at the entrance of my manhole. She rubbed it’s head on my rectum until she felt me loosen up. Then without warning she rammed the full length of it into my ass. I screamed in pain as my ass locked around its wide girth. She smiled then stuck the finger she had just had in my ass into my mouth. “Suck it bitch!” she said. I followed her orders. She began to fuck my ass with long slow thrusts. The pain began to subside and make way for pleasure. I began to moan and buck my hips to meet her rhythm. Having someone else fuck my tight ass felt really good. After a while she was full on fucking me, her hips loudly slapping against my ass cheeks. Waves of pleasure ran through my trembling body. She pulled her finger out of my mouth and threw the little pink panties onto my face. “They feel awfully crusty.” She remarked. She then grasped my rock hard dick and began stroking it. I reached up and grasped her breasts as they bounced with her fucking motions. After no more than a minute of pure ecstasy I felt my climax coming on. I began to moan, Maria didn’t slow down a bit and then I began to cum as she stroked my cock. I came so hard, my cum hit my face and chest.

“Well that didn’t take long.” Maria stated. “Don’t worry, we are not done yet. She took off the strap-on and walked over to one of her closets. I admired her plump round ass as she walked over there, her pussy lips peeping out at me with every sway of her hips. She rummaged around in her closet and pulled out a large butt plug and a rubber cock ring. She came back over to the bed and lay on top of me in a 69 position. She slip the cock ring on my now semi hard cock. She then began to suck my cum drenched penis. I gladly returned the favor and began eating her pussy. I tickled her large clit with my tongue, her pussy juices were sweet to taste. Soon my cock was fully erect again as she gave me the best blowjob I had ever gotten. We continued this way for a good fifteen minutes before she broke the silence in a desperate command, “Lick my ass”. I did as Maria instructed. She then began to insert the large but plug into my ass.

I cried out in pain when it was about halfway in me, “No Maria stop it hurts too much.” Just as I finished saying that she rammed it the rest of the way in. Intense pain enveloped my bowels and then it went all the way in, my ass clenching around its base as it locked itself in me. She turned on the vibrator and once again I was in ecstasy. I continued licking her ass, sliding my tongue into it, she responded with whimpers of pleasure. She handed me the small butt plug and told me to fuck her ass with it. I slid it into her ass and turned on its vibrator. I began to eat her pussy again. She sucked my cock and then stopped, and told me to really fuck her ass with the plug. It did as she asked me to. Ramming it in and out of her cute pink asshole. Soon she stopped and cried out, “Fuck my pussy, Steve, Fuck me hard, I have been waiting so long for your cock to fuck my pussy.” I rolled her onto her back, leaving the plug in her ass, and with no hesitation slid my cock into her shaved pussy. Her pussy willing accepted me, she was dripping wet, I slid into her warm depths with no problem. As I fucked her I pinched her tities. She moaned and cried out in pleasure. I fucked her hard for at least ten minutes until she began to cum. She started crying out in pleasure as I felt her pussy and legs begin to tremble. She began to scream out at the top of her lungs “Fuck me Steve, oh yes, I am cumming, Fuck me hard.”

After her climax started to wane I pulled out of her. She embraced me and we kissed. She then said “we are not done yet, I want you to fuck my ass, cum in my ass Steve.” I rolled her over and she got into a doggy style position. I pulled the plug out of her ass and slid my cock in. It was the first time I had ever fucked a woman’s ass and it felt good. I reached around and held her breasts. She stated fingering herself while I butt fucked her. Then she grabbed the butt plug, it was still vibrating, and she began to masturbate her clit with it. It was not long before Maria was quivering and having another orgasm. She screamed and moaned in pleasure. I continued ramming her ass, pulling all the way out and then ramming back into her, piercing her rectum. The plug in my ass was still pleasing me, stimulating my prostrate. She cried out for me to keep going, she was having multiple orgasms. I fucked her ass until I felt my second orgasm coming up. I moaned her name as I came into her tight ass.

We both fell limp on her bed. We embraced and kissed, our tongue dancing with each other. Soon we had dozed off into an after sex slumber. I didn’t know how long we slept. We awoke to someone entering her house. The dog began to bark. I asked her if she was expecting someone. She said no, as we heard the footsteps heading up the stairs….


2015-05-19 02:10:14
What a great story!

anonymous readerReport

2012-06-18 12:31:25
Captivating story. Well written. One of the few that held my attention from beginning to end. jimjr1945


2012-04-12 02:01:10
As a crossdesser since very young, i can relate to this.well done good story.

anonymous readerReport

2012-03-01 12:16:33
Everyone wants afriend like maria

anonymous readerReport

2011-11-10 08:13:22
My wife fucks me with a strapon while I wear panties, so I can relate to this stories.

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