My girlfriend, Sherry, had nice, big C-cup titties and a face like a young Marilyn Monroe. Needless to say, she got hit on by lots of men wherever she went. She was also a nyphomaniac who liked to be fucked ten times a day, so we had a great sex life.
She found out I enjoyed wearing lingerie, so, as part of our sex play, she would dress me up in her panties and bras and stockings and put lipstick and makeup and eye shadow on me. This kept me hard for her for hours and she really enjoyed all the good fucking I gave her while in drag, especially on weekends when we could spend all night and day in bed together.
This went on for about six months and I really liked being turned into a woman by Sherry, but I had a feeling that something was missing from our sexual game. As a sexy woman, I felt the need to have a man involved in our game to give me the feeling of really being a woman.
My chance to bring up the idea of having a three-way with another man came unexpectedly. Sherry had to walk home from work and a summer shower came up. A handsome stud had picked her up and given her a ride to get her out of the rain. The fact that her nice tits with big nipples were visible through her white blouse must have turned the guy on, because he gave her his number on a pack of matches.
When I got in Sherry's pocketbook for a light, I discovered the pack of matches with another man's number on it and confronted her.
"Oh, yeah, he was really nice and gave me a ride in the rain so I didn't want to be rude and not let him give me his number."
"Was he handsome?" I asked.
"You know, we weren't together long so I really didn't notice."
I saw the opportunity to present the idea of including another man in our sexy fun dress-up game we liked to play on weekends.
"Do you think he has a big cock?" I asked.
Sherry smiled slyly. "I did notice he had big arm muscles and looked like he worked out at the gym."
Now, I smiled. "So, you wouldn't mind fucking him if you had the chance?"
"I don't know," said Sherry. "You do me really good. But if I wasn't with you, I'd probably call him and make a date."
"I'm thinking maybe you could make a date with him for both of us," I said. "We could both get to enjoy his cock."
"Really? You'd suck another man's cock?" she replied.
"The thought occurs to me every time I'm dressed up like a woman. And, while I like sucking your pussy, I've been wondering what it would be like to have a man's cock in my mouth, instead."
Sherry smiled widely. "That is so hot," said Sherry. "Thinking of you dressed as a woman and sucking a big cock kind of turns me on."
"Why don't we try it then?" I suggested."It would spice things up and then we could both take turns fucking you for hours the way you like to be fucked."
I saw Sherry's nipples getting hard in her blouse and knew she loved the idea of being tag-teamed by her boyfriend and a stud from the gym. And it would be a dream come true for me, too. If her new friend was as big as she said, I'd feel just like a sexy woman and be glad to suck his cock. Of course, it was all up to Sherry. I knew no man would pass up a chance to fuck her, even if it meant they had to be sucked by her boyfriend first. That's how hot Sherry was.
Sherry moved toward me and put her arms around me then ground her cunt into my dick through our clothes. "Baby," she said. "The thought of getting fucked by a big stud from behind while I suck your cock is making my panties wet. I never thought of it before today. But it does sound so hot."
"So, you'll do it?"
She smiled. "Sure. This weekend."
We kissed and started fondling one another and it wasn't long before we were in the bedroom doing it in every position until we passed out later that evening.
Sherry called her admirer whose number she had on the pack of matches, and set up a time to have a drink with him at the local pub. We figured it would be better for her to make the proposal in person than on the telephone. He would be looking at Sherry's nice tits and her naturally pretty face and be all horny for her, so he would be more willing to let her boyfriend suck his dick just so he could put it in her.
On the day of Sherry's meeting with her admirer, we both got ready together like two girlfriends, washing each other's hair and doing our makeup and putting on sexy lingerie. It was a thrill in itself for me since I had a fetish for women's undergarments and was always hard as a rock while wearing them.
Sherry was one of the hottest women in our town and seeing her when she was dolled up was always a thrill. My friends had told me how hot they thought she was and they would stare at her whenever they came to visit. I was proud of her beauty and never felt threatened by other men since we had an incredible sex life. I figured it was no threat for them to want what I was getting plenty of.
This night would be the first time I ever shared Sherry with another man. She was such a sex maniac, anyway, so having another cock to suck and fuck would be sure to make her happy. As far as me being in drag and sucking cock, too, it seemed a natural extension of our sexy game playing so it didn't feel gay, at all. It was just kinky fun by consenting adults.
Before putting on her sexy lingerie for the evening, Sherry let me watch while she shaved her pussy. She sat on the edge of the tub and shaved every hair and even fingered herself for me while she did it. Her pussy was really getting wet from all the attention her fingers were giving her clitty and I had a big hard dick from watching her, so we had a quickie before we got into our lingerie.
Sherry wore her purple lace bra and panties. Purple was her favorite color and she called it "the color of passion." I opted for a sexy black thong panty that showed off my ass, a black lace bra and a pair of silky black stockings. When we were both dressed in our lingerie, we kissed and the feeling of Sherry's tits pushing against my black lace bra gave me an instant erection.
"Baby, you look so good," I said. "There's no way this guy is going to turn us down."
"If he does, I'll come right home and fuck you good," said Sherry.
"You can see I'm ready for it."
She looked down and saw my fully erect cock standing at attention and trying to get out of the sexy black thong.
"I want to suck it for you, right now," she said.
"I've been watching how you suck cock for the past six months and I want you to show me how to do it with our guy tonight. If his cock is as big as you say his arm muscles are, it's probably not going to be an easy one to suck."
"The trick is, whatever you can't get in your mouth, stroke with your hand. He'll love it."
I said, "I like the way you suck on my nuts. Maybe you can suck on his nuts while I suck on his cock."
Sherry smiled widely. "Good idea, baby. It's so kinky to think about, I'm getting horny again."
"Let's not get our panties wet thinking about all the fun we can have," I said. "Let's wait until we have him here and can tell him what we want to do to him."
"What if he wants to put his hand down my panties and play with my pussy on the way here?" said Sherry. "Should I stop him or let him?"
"Stop him," I said. "But rub some of your pussy juice on your finger and let him have a taste of it. That will keep him good and horny for us. Tell him he can't have your pussy until your boyfriend sucks his cock."
"That's hot, babe. Talking dirty gets my juices flowing."
"Mine, too. We are just a couple of horny sluts tonight, so let's have fun. We have some condoms left for when he fucks you, don't we?"
"Then we are all set."
Sherry slipped on a black cocktail dress that showed off her nice legs and revealed her big C-cup breasts very well. And I put on her black negligee over my thong, bra and stockings. We were now both hot women wanting some strange cock and, as hot as Sherry looked, we were hopeful of getting it.
Sherry walked down to the local pub to meet her admirer looking so hot that it was a wonder she didn't cause men driving by to wreck looking back at her. I was proud of my super pretty, well-built, extra horny girlfriend as she left and I was suddenly glad to be sharing her with another man who wanted her, too. Strangely, after this night, this would become a ritual we would both look forward to every weekend.
At the bar, Sherry met our date and explained to him that we were trying a new adventure in our sex life and wanted him to be our first man we shared together. He was reluctant at first, then Sherry reached under the table and started stoking his big cock through his pants.
"Does that feel good?" she said.
"Yes," he replied.
"Well, my boyfriend's lips on your cock will feel good, too."
After having two drinks together, Sherry had our date so turned on there was no way he could resist her demands.
"How good does your pussy feel?" he asked.
"My boyfriend likes to fuck me ten times a day."
He smiled. "Really? You take that much cock in you?"
"I love having that much cock in me. And I know I'm going to love having yours in me, too, after my boyfriend gets it wet with his tongue."
"Man. you're really turning me on. I'm just not sure about having a guy blowing me."
"He's all made up as a woman, so you won't feel like he's a guy. We've been role playing for months now, so it's just something new he wants to try with me."
"And you want to do it, too?"
Sherry pulled down the cups of her strapless cocktail dress and purple bra and showed him her breasts in the dark bar.
"Do you see how hard my nipples get when I think about it? Down in my little panties, my pussy juices are flowing out, too."
"Oh, baby," he said. "Let me feel it."
He reached down under the table and put his hand up Sherry's dress and pulled her purple panties aside.He put his big fingers in Sherry's wet pussy and started fingering her good. When he did, she reached for his boner and felt it getting totally solid. A kiss on his lips from Sherry sealed the deal and she was soon on her way home to me with the first stud she would bring me.
It was true that the thought of having a three-way with two men was turning Sherry on immensely. She told me later how happy she was when I suggested it. We had a happy relationship together and were good friends besides being lovers, so there were no jealous feelings in either of us. The fact that we both liked the same hard cocks actually made us grow closer. Sometimes we would suck on a cock at the same time while we gazed in each other's eyes, making us both feel wonderful.
When Sherry entered our apartment with the tall muscle man, I was as nervous as a girl on her first date. After all, I knew what a man wants from a woman and I was coming to terms with the idea of sucking my first cock. How many girls have gone through the same nervous emotions, I wondered. Would he think I'm pretty enough? Would he be rough or gentle? What if he trys to make me swallow his cum?
When I told Sherry about this later, she said it reminded her of her first time giving a blowjob to a man. She had been waiting for a bus when she was 17 and an older man picked her up and gave her a ride. He turned the conversation to sex and asked her if she had ever given oral to a man. She said no, and he told her it was time she learned. They went parking and she sucked him off really good and learned how much she enjoyed it. She said sucking cocks good made her feel special. So, she was happy to hear I enjoyed it, too, after our first date came calling.
I don't know how other guys feel about their girlfriends, but mine was so damned hot that it was a tremendous thrill for me to share her with big studs. Seeing how turned on she made them after just meeting her became a turn-on for me in itself. When she brought them in the door their cocks were already hard and she soon stripped them out of their clothes and got them naked on the couch. Then I would join them and get to suck their cocks while Sherry kissed them on the lips. This way they weren't paying attention to me and were concentrating on her while I enjoyed giving head to them.
We hadn't discussed how we would proceed when Sherry got our date home. I was in the bedroom and let her have the living room. After coming in to let me know she brought him, Sherry went back out and stripped out of her cocktail dress while he watched. In just her purple lace bra, panties and high heels, she proceeded to remove his pants and shirt and underwear while I watched from the bedroom.
When I first saw how big his cock was, my heart started pounding faster. He was 6 feet 4 inches tall and had a humongous boner, at least a foot long. My panties got wet with pre-cum while looking at it. What a little wench I am, I thought. The sight of a big cock was turning me on and I didn't even have a pussy to put it in.
When I came out wearing Sherry's black negligee, she was kissing our stud with an open mouth. Both of them were twirling their tongues together. And I couldn't wait to twirl my tongue on his big 12 inch cock. Oh, the excitement of becoming a full-fledged cocksucker was too much. It's what Sherry had felt when she got picked up by the first man she had given oral to and it was what I was feeling. It's no wonder to me that so many men get into it. We are sexual beings and giving oral is so universal.
When Sherry and our date noticed me in the room, they stopped kissing for a moment. Both looked at me. Then Sherry spoke.
"This is Curt, honey."
"Hi, Curt," I said.
He smiled. "Hey, you know, you don't look bad in that get up. Pretty sexy," he said.
"It's mine," said Sherry. "Like I told you, we got into role playing. But you're the first man we've had join us." Then Sherry looked at me. "Curt gave me a ride that day I was caught in the rain, wasn't that nice of him, honey?"
I nodded yes.
"Oh, man," said Curt. "The way you could see your nipples through that wet white blouse, a thousand guys would have stopped and offered you a ride."
Sherry smiled at him."But you did, baby. You're my knight-in-shining armor." She reached down and grabbed his immense cock and held it up to me. "Doesn't he have a nice cock, honey."
I smiled. "He sure does."
"I can't wait to feel it in my pussy. But I told Curt you have to suck it first."
"Come over here and let me take you out of that negligee," said Curt.
This was the first interest he showed in me and it broke the ice between us. Like a sexy woman on the loose, I stood with my back to Curt while he undid the buttons and loosened the waist strap on the negligee. As the sheer black gown fell to the ground, I felt so feminine. And Curt was happy when he saw my hot ass in the little black thong.
"Woah, boyfriend," he said. "You have a nicer ass than Sherry does."
Sherry laughed. "I tell him that, too."
"Well, I'd like to fuck his ass while I suck your titties"
The thought of getting my ass fucked by a 12 inch cock sounded thrilling to me and I was hoping Curt was not joking. While we had only discussed me sucking his cock, it seemed a natural progression in my dual life as a woman to be fucked in the ass, as well. Having Sherry let a man suck her big C-cup titties while he fucked me in the ass became a trick we used to get men who weren't bi-sexual already into the act and I was glad Curt had suggested it.
Now, I was simply a sexy little slut who wanted to devour a big cock for the first time and I felt all the fear and inhibition leaving me. By discussing what we wanted aloud, it took the nervousness out of the situation and I was ready for Curt to feed me my first cock while he kissed Sherry and played with her tits.
Sherry was fantastic that night and so helpful and understanding. She knew every emotion I was feeling and seemed to be feeling them, too. We were both a couple of nymphos who needed men's big cocks to please us and we were discovering more and more about our sexuality. Before the night was over, we would discover how much Sherry enjoyed having me put my cock in her ass while Curt fucked her from the front. Later, after Curt fucked me in my ass, we would come to learn that we both felt similiar feelings down there and we grew to understand each other's need to be dominated by a man's cock.
It was amazing discovering all the positions we could do together by adding another man to our bed. But, right now, I just had to get my lips on that big cock of Curt's. He was handsome in a rugged way and I was not jealous of him since my interest in him was heightened by his good looks. Call me starnge, but I really learned to enjoy looking at a handsome man with a big cock while I sucked him to completion and I hold nothing against any man or woman who does the same.
My only concern was Curt's reaction when he saw my own cock down in my little black thong. From behind, I looked totally like a woman but from the front I was afraid I might scare him off. I had my back to him still and did not turn around for a moment.
"Why don't I get us some drinks in the kitchen while you two kiss some more?" I said.
"Sure, a beer sounds good," said Curt.
"I'll take a glass of wine," said Sherry.
I proceeded to walk toward the kitchen while Curt enjoyed the view of my nice ass in the black thong.
"Baby, your boyfriend has a nice ass," he told Sherry.
"I bet you before the night's over you're gonna want it like my pussy," she said.
Then she started kissing him again while I went to the kitchen for a beer and two glasses of wine. I decided to drink wine, too, since it would make me seem more feminine to our manly guest. When I returned from the kitchen they were kissing each other and Sherry was taking off her purple bra so Curt could suck her tits. This was my chance to get to his cock while he sucked her tits and didn't notice my cock and balls in the little thong.
The sight of Curt's tongue twirling around my girlfriend's tits was such a turn-on I hadn't expected. All I had been thinking about was the pleasure of twirling my tongue around his big hard 12 inch cock. Now, I was even more turned on than I could have imagined. Knowing Sherry would be getting lots of pleasure from this hadn't occurred to me until I saw the passionate look on her face while Curt sucked on her big nipples, alternating between the two of them.
After I set our drinks down, I quickly took a seat on the floor in front of the couch. I reached for Curt's big 12 inch cock like it was a new toy I could play with. He was sucking on Sherry's tits and didn't notice me, at first. The feeling of having his boner in my hand was incredibly sexy and I knew at that moment that pleasing men while dressed as a woman would become a favorite sex act of mine. Suddenly, Curt noticed me stroking his mammoth meat.
"Who's that down there?" he said.
I spoke with a sexy girly voice to my new lover. "Hi, baby, I'm Fellatia, your new girlfriend, the one whose ass you like. Remember me?"
"Hell, yeah, I remember. I never forget a good ass."
"Is it okay if I have your cock, Big Curt."
"Oh, yeah, Fellatia. Suck it like a good slut."
I looked at Sherry."Sherry, why don't you help me. I'll pick up where you leave off."
"Oh, yeah, having two hot bitches suck my cock sounds even bettter," said Curt.
Then Sherry asserted herself. "I think you should have it, first," she said. "After all, you're the bitch who wanted it. You told me after you suck it, I can fuck it. Hurry up and get sucking, baby, so I can fuck it, soon."
Whatever it was about Sherry's words, after all she was being my coach, but I suddenly felt the freedom to suck Curt's cock like a girl. We're just litte bitches and expected to do our duty for a man and that is what Sherry was telling me. Every bitch wants cock to please and, right now, I was that bitch and this was my cock, the first of many I would come to want.
With a big smile on my face, I leaned forward and put the big head of Curt's cock inside my lips. A million emotions ran through my body as I realized this was it. I was now becoming a horny little cocksucker who needs men to please every time she wears panties.
Suddenly, I remembered how I had first started dressing up for Sherry. One day, I came home from work and saw a pair of Sherry's panties on top of the laundry basket. They were just a regular cotton pair with flowers on them but I picked them up and noticed there was a wet spot in front where her pussy touched the panties. I smelled the spot and the pungent aroma of Sherry's pussy juices made me instantly horny.
Having her panties in my hand while getting a hard-on, I decided to strip out of my clothes and put them on. Like I said, they weren't her sexy, silky panties, just a regular cotton pair, but they still made me feel incredibly sexy and horny to be wearing the little bikini bottom with flowers on it.
I laid down on the bed wearing only Sherry's panties and I started rubbing my cock through the panty. Suddenly, I felt like a girl laying on her back on a bed waiting for a man to fuck her good. The feeling was intense and I felt like my hard-on wouldn't be satisfied until I had a big hard stud's cock to please. It didn't occur to me then, but now, with Curt's cock head in my lips, I was realizing when I first felt like sucking a man's cock for him.
I had started wearing Sherry's panties around the house when she wasn't home and when she caught me one day, instead of being mad, she thought it was cute and kind of kinky. That's when we started playing dress up as our sex game. And since Sherry was going to beauty school at the time, she liked putting makeup, lipstick, and eyeliner on me for practice.
Now, here I was, totally dolled up like a beautiful woman, wearing a sexy thong, bra and stockings and sucking on a strange man's big cock. It was the kind of cock that men like to brag about having, so having it in my mouth made me feel dainty like a little lady with her big man.
All the sexual feelings I felt playing dress up with Sherry were culminating in this moment. The fact that I could never go back to just having straight sex with women didn't occur to me. I didn't know I was going to enjoy sucking on men's cocks until I had Curt's cock in my mouth and felt the sexual power that big cocks have. I felt like I was just a sexy girl with a little clitty in my panties while I was between the big strong legs of a hunky man.
"Ah, babe, you're really good," said Curt as I sucked his big twelve inch cock and stroked it.
Sherry's advice about stroking whatever you can't put in your mouth was really helpful.
"Suck it, baby, suck it," said Sherry.
Encouraged by Sherry and our suitor, I started putting more and more of the mammoth cock in my mouth and slurping on the sticky pre-cum that was oozing out of the tip of it.
"Oh, yeah, oh, yeah," said Curt. "Suck it like a good little bitch."
I was really working it good with my eager mouth and stroking the big shaft which made my hand feel so small. This was it, I thought, I was now a full-fledged cocksucker like Sherry and all my fantasies about doing it were becoming a reality.That fantasy that started that day I wore her flowered, cotton, bikini panties and laid on the bed feeling like a woman wanting a man. And knowing that Sherry was the one who got me the man made me realize how much she loved me. There was nothing she wouldn't do to please me.
While I stroked Curt's cock and sucked him, Sherry was busy kissing him.With my free hand, I reached over inside her purple panties and slipped my fingers inside her sloppy pussy that was already wet from all the horny action with our big stud.
It was no wonder that big cock studs would become my very favorite ones to please. Curt's big cock made me feel like such a horny little slut I wanted to suck it all night. I was just being nice to Sherry by fingering her pussy. The large cock in my mouth was what I really wanted. It was the reason I was feeling so much pleasure down in my little thong panty. Men were welcome to fuck her pussy all they wanted, as long as I got to suck their cocks first.
The intensity of having two feminine beings giving him pleasure was too incredible for Curt. I was happy that Sherry had insisted on me sucking his cock by myself. This way, I knew that I had what it took to please a man orally. Otherwise, I would just have figured they were only wanting her wonderful lips. So, when our big stud started spewing cum in my mouth, I felt like a sexy little dollboy being rewarded for her efforts. The milky, salty sperm quickly filled my mouth and our stud was still cumming.
I pulled my head away but still stroked his thick twelve inches for him while more loads of cum continued to spew out. That's when Sherry came down and licked up some of it, too. It was so hot watching my girlfriend with her bright red lips going down on another man's love tool that I forgot to swallow the load in my mouth.
When she finished slurping up the rest of Curt's warm cum, Sherry looked at me and smiled. She knew we were sharing the same delicious pleasure of being sexy little sluts for a man and she was glad to see how much I enjoyed being like her, a cum-hungry bitch who can't get enough cock in her and always wants more. It felt like I was becoming like Sherry.
She looked at me and said, "Now, swallow it, baby. Men love it when you swallow their cum. It makes them feel like their cocks have power over you."
I did as Sherry told me and we held hands as we both swallowed our lover's warm cum at the same time. It made us feel really close like two girlfriends sharing the same boyfriend and it became something we both enjoyed doing every weekend.
"Mmmm, baby," said Curt to Sherry."Your boyfriend sucks cock really good."
Sherry smiled like a proud teacher. "He should. I taught him, myself."
It was true that Sherry was the woman who had given me the most blowjobs and the one who enjoyed doing it the most. The fact that I would become an expert dicksucker who lots of men enjoyed getting blowjobs from was inevitable after being with such a gifted slut as Sherry. We felt like sisters at that moment.
After we finished swallowing all Curt's scrumptuous cum, we made a toast with the drinks I had brought us. Sherry and I were still seated on the floor between Curt's legs as we toasted with wine and Curt with a beer to "new friends."
Now, it was time to get Curt's big tool ready for action with Sherry. I did the honors by reaching for it and stroking it a few times for him.
Sherry said, "Honey, you want to suck it some more?"
I smiled up at Curt. "I sure do. But I think you need to fuck him instead and give me a blowjob while you do it."
"Shit, yeah,"said Curt."That sounds hot as hell."
"She likes to be fucked from behind," I said. "We can go to the bedroom and I'll lay down for Sherry to suck and then you come in in a few minutes and slip it in her from behind."
The pressure of my fingers and palm on his cock and the thought of fucking Sherry's wonderful pussy was making Curt hard again. We were in for a long night because Sherry loved being fucked and I knew it. As soon as Curt would shoot his load into a rubber and pull it out of her, I would slip mine in and we would keep her filled up good.
One time, when I went to slip it in her from behind the way she liked it, my cock accidentally went into her asshole instead. She quickly said,"Ohhhh."
"What?" I replied.
"That felt good," she said. "Why don't you slip it in me there again?"
I did as she told me and I saw the ecstatic look on her face. It was as if she had her vibrator on full speed and was thrusting it inside her pussy. But I was in her ass instead with my fully erect cock. I reached around her and started fingering her clitty while I fucked her ass. This was completely driving her wild.
"Oh, fuck, I love this," said Sherry.
"Why don't we have Curt put his cock inside you, too?" I said.
"Oh,yeah," she replied.
I rolled us over and laid on my back with my cock in her ass still. Her shaved pussy lips were fully exposed for Curt who was hard again and ready for action. He approached between both our legs and when he did he saw my tight little asshole down between my spread legs and, suddenly, he wanted my ass as much as he wanted Sherry's pussy, although he didn't say it right away.
Curt slipped his big twelve incher in my girlfriend's bare wet pussy and started playing with her big tits while he pounded her hard. With my cock in her ass, the feelings were intensified and she was soon moaning loudly as we tag-teamed her good.
"Oh, you big fucking studs," she said. "I can't get enough of your big cocks inside me. And now having two at once, I can't stand it. Fuck, fuck, fuck. This is so fucking hot."
It really was hot. Through the thin flesh between her ass and pussy, I could feel Curt's big cock every time he thrusted into Sherry's pussy and it felt like we were rubbing our dick's together inside her. I started getting horny for Curt's cock again and looking up at his handsome face made me feel so girlish.
When we finished giving Sherry "a double delight" as we came to call it, I went back after Curt's cock with my lips and tongue for the first time since the start of the evening. He had incredible staying power and was made hard again when Sherry started licking his big balls while I sucked on his big cock head and stroked the shaft. In no time, he was ready for some more action.
I was completely surprised when Curt started feeling my ass cheeks with his big hands.
"What's up?" I said.
Curt smiled at me. "I remembered what a nice ass you have when I was between your legs and you were spreading them."
I smiled."You told me you liked it when you took off my negligee, too. Remember?"
"I sure do," said Curt smiling.
"So you want to fuck me in the ass while you suck on Sherry's tits?"
Curt smiled and nodded.
Sherry said, "That will be good. My pussy needs a little rest from you guys for a few minutes." Then she looked at me. "But are you sure you're ready to get fucked on the first night with a man?"
"No better time to find out than now," I replied.
There was something very girlish about getting on my hands and knees for a man to put his cock in me from behind. And the anticipation of it gave me a rush of emotions through my body. This must be how a woman feels when she is about to get fucked, I figured. Every one you get must give you new, warm feelings inside you and become a habit you enjoy pursuing. I imagined that was why Sherry liked having my cock inside her ten times a day, seven days a week.
Sharing my first fuck from a man with my girlfriend was quite special. It didn't occur to me at the time that I would start to want to be fucked by a man all the time, too. It was just something I was doing to please our new friend, Curt. But like I said, the feelings welling up inside me were so incredible when I bent over on my hands and knees for him that I was, at once, destined to become a slut who likes cock in her.
They say every girl remembers her first time being fucked and I was no different. He got behind me and played with my ass cheeks and this removed the nervous tension I was feeling. Looking back over my shoulder, I saw his big twelve inch love tool was fully erect again.
Sherry pulled a fresh rubber on his dick while he licked a finger and put it in my hole and started wiggling it around. So, this is what a girl feels like being fingered, I thought. It gets her ready for something bigger to have in her. It's just a tease compared to what she really wants in her.
With my sexy girly voice, I said, "This is my first time, so take it easy, okay?"
Curt smiled deviously. "Okay, bitch," he said as he slapped my ass cheek with his free hand.
Sherry and I were both surprised when he said, "This isn't the first ass I fucked. I was the center on our football team in high school and used to get turned on when the quarterback put his hands between my legs. Finally, one night I made him let me fuck his ass for turning me on so many times. I liked his ass as much as any pussy I'd had."
It was comforting to know that my hunky stud was an experienced ass fucker and probably very good at it. The fact that his cock was fully erect let me know he wanted me badly. It made me feel so good to know that my first lover was just as turned on by my ass as he was Sherry's pussy. In fact, earlier that evening, he said I have a nicer ass than Sherry.
Boosted by my feminine confidence, I said, "Fuck me good, you big hard stud."
Sherry and Curt both smiled.
"Do you hear that?" Curt said to Sherry. "Your boyfriend wants me to fuck him good."
"I'm totally surprised," she said. "I never knew what a little tramp he was."
"If he dresses the way he did tonight, he could probably go down to the bar and get his own dicks to suck. He won't need you to do it for him anymore."
They both laughed.
"Well, you did say you liked my ass better than Sherry's," I said.
"Hell, yeah, I do," said Curt. "And when I saw this tight little hole of yours, I wanted it even more."
The size of the big mushroom head on his hefty cock made me nervous when I thought about him putting it in my tight little hole. I am sure every girl feels this way her first time with a man and I was glad to have those same feelings. I reached up and started playing with my tits with one hand to remind myself how much I like feeling like a woman. It was incredible.
After Sherry finished pulling the rubber over Curt's dick while he fingered my hole and played with my ass cheek, she got the Vasaline out of the night stand. We sometimes used it when she was getting dry from too much fucking. Now, it was time for her to use it on me. What a switch, I thought. I was now the horny bitch in the room who needed a man's cock inside her and nothing could stop my desire.
"Fuck me, damn it," I said to Curt.
He laughed. "You're gonna get it good, bitch. Don't worry."
Sherry held out the open jar of Vasaline and Curt took a scoop and shoved it in my waiting ass while Sherry rubbed some on his condom-covered cock. I saw the thrilling look on her face as she stoked his big man tool and I could tell she knew I was getting a very large cock for my first one. It couldn't have been any better, as far as I was concerned. Being a girlish man, I needed a man with a big one to make me feel more womanly.
I spread my legs and ass cheeks wide in anticipation of Curt's big manhood entering me, any moment. This is the feeling that every girl looks forward to and I was about to join the club, the slut who loves cocks inside her club. It has a lot of members, I'm sure.
Feeling the rubbery tip of his cock touching the skin around my ass sent a wave of sensations through my body. Am I really a girl, I wondered. Oh, it felt so good, I didn't want to feel like a man anymore. I wanted a dominant man to give me this feeling every day.
I looked at Sherry. "Honey, why don't you go get us another drink?" I said. "And take your time."
Sherry smiled, knowing I was feeling the same way she feels when a hard cock is about to go in her. She left the room, leaving me alone with my first big stud I would ever have. The three-way was over. I was about to become a full-fledged woman who loves big cocks and wants them every day. After this night, I could never turn back. I was never going to be satisfied by pussies the same way, ever again.
When we were alone, Curt said, "What's your name again, baby?"
"Fellatia," I replied.
"Okay, Fellatia, this might hurt you a little bit. But I'm gonna put it in you anyway, so don't try to stop me, honey."
I said,"Give it to me hard, big boy."
That was all the encouragement my big stud needed. I was now a horny little slutboy who wanted men's cocks day and night just like my girlfriend, Sherry, whose horny little pussy never seemed to be satisfied. Although she had brought the man to the house, he was now all mine and I was about to use my feminity to please him just as a woman does.
When the head of his cock entered my ass, I let out a loud sigh. "Ohhh, yeah. You're so big, baby. You make me feel like a little seventeen year-old girl with her daddy. Fuck me good, daddy."
Holding both my hips with his firm hands, Curt plunged more of his cock into me and the sensations shot through my mid-section like electric wires.
"Ohhh, yes," I said. "Fuck me, daddy, fuck me."
With each inch that entered me, the sensations in my gut got more intense. I wondered if this was what a woman felt. Did a cock in her feel this good? No wonder so many of them like it, I thought. When he finally worked the whole big twelve inches in, I felt like a dirty little slut, all the sudden. And I could relate with those feelings that some women get, too.
But when he started thrusting his big love tool in and out of my hot little bottom, I felt a connection with him that seemed so natural. It was as though our bodies were becoming one. I especially liked it when he pounded it into me and I felt a thousand sensations in my gut. It was also intense feeling our balls slapping together like they were made for each other.
Up until this point in our sexual adventure, I had felt like it was all just a game. But with this newfound joy Curt was giving me, I was starting to look at this in a different light. I felt like a woman trapped in a man's body and needing everything she gets from a man. It was no longer a sexual game to spice up our love life, but was becoming a new identity for me. I was a sexy, slutty bitch with a huge twelve inch cock in her and it made me feel very speacial.
The fact that he kept pumping me let me know he liked it, too. I started wanting to perform for him like a woman.
"Oh, yes, fuck me, fuck me, you big stud. Your cock feels so good inside me. I want it every night from you, baby."
"That's a good bitch," said Curt. "Take it in you like a girl and please your man."
"I looked back over my shoulder at Curt. "You're damned right I want it in me, you handsome fucking bastard. Forget Sherry. I want your cock in me the rest of the night. She can use her fucking vibrator. You're my stud, now, handsome."
Curt laughed. "You for real?" he said.
"Hell, yeah, I am. I want it as much as she does. And then I want us to sleep with it between my legs, so I can wake up in the middle of the night and suck it and get it hard for you so you can fuck me some more, the way Sherry does me."
"She won't get jealous that you like my cock more than her pussy?"
"I wouldn't care if she did. Fuck me like I have a pussy,"I said.
He started thrusting in me harder and we got into a steady rhythm that I thought only a man and a woman could establish. He was a 6 foot 4 stud with a big cock and he was all mine, at this point. Nothing would make me ever want a stinky little pussy again when I could have a big cock instead. I was sure about my feelings. I was truly Fellatia, a sexy nympho who had made her first conquest of a man.
The fact that taking cock in me felt so wonderful was heartening to learn. All the nights I had spent playing dress up with Sherry had all been practice for this moment. The sexual feelings I had for Sherry while we played dress up together now seemed misplaced. We had just been like two lesbians getting it on back then. This is what I had really wanted all along and was just coming to realize it, now.
Strangely enough, I didn't feel gay, one bit. Gay to me was a guy wanting to suck another guy's dick. But I felt like a girl wanting to suck a guy's dick and fuck him and it felt so natural. I wasn't worrying about satisfying my own dick. I was only interested in satisfying my new boyfriend's cock so he would want me more and more. So, this is what a little slut feels when she is with her first man, I thought.
The sound of Curt's big body slapping against my ass was loud as were the springs in the bed, so I didn't hear Sherry come into the room and crawl up underneath me and start sucking on my cock. This was it. It was intense to be having my girlfiend suck my cock while my first boyfriend fucked my ass good.
Damn, it felt so good to have a girlfriend who was as slutty as me. We were starting a new chapter in our love life. We could find men to share together like two girlfriends and act out all our desires, sucking their cocks together, letting them fuck us in the ass and sleeping with him between us.
That was how it went from that weekend on. We lined up a man during the week to come spend the weekend in bed with us having sex and both of us tag-teamed him. It was always a pleasure and I'm sure we could have gone on doing it longer than the few months we did it. But something happened that changed all that.
One weekend, Sherry came home from the bar with two men instead of one and she told me that one was for her and one was for me. I was nervous about it, at first, like I was the first night with Curt. But Sherry assured me that my date loved trannies and would be very happy with just me.
Bill was his name and he became my first true boyfriend. I was already in drag and we pulled out the sofabed so we could spend the evening in the living room while Sherry took his friend Terry into the bedroom for the night. I didn't know if Sherry had planned it this way, but being with an experienced tranny lover like Bill was the beginning of my serious life as a crossdresser. Up to this point, we were just playing dress up.
But after I pleased Bill for many hours as a woman, my desire for him was too much. No other man had kissed my lips like he did and rubbed me all over my body. His cock was only eight inches long, but I came to love sucking it for him that night because I felt like he was my real boyfriend and not just a guy who wanted to fuck Sherry.
Looking back, I realize she did me a big favor that night. I probably never would have found a man as understanding of my needs as a crossdresser as Bill was. He liked giving me massages while I was dressed up as a woman and telling me how sexy I am.
Sherry later told me it was her date, Terry's, idea to set me up with Bill so he could have her all to himself. And while there is a little melancholy feeling when I look back on my relationship with her, I'm sure that the desires in me to be with a man were never going away after that first night with Curt. Curt, whose big cock had given me such intense pleasures that I would never crave another pussy again. Oh, my big stud, Curt, my first blowjob and fuck. The man who first made me feel like a woman.
I've enjoyed telling you all about my first night with Curt and I'd like to tell you about my first night with my first boyfriend, Bill. It was really special and I've never forgotten it, either. I remember all the details.
When Sherry first went into the bedroom with Terry for a wild night of sex, I sat Bill down on the couch and took off his tie and his dress shirt. He was a little taller than me. I was nervous to be alone with him without Sherry there to help me like a good girlfriend, although I was wearing her bra, panties and stockings which gave me confidence that I was attractive like her.
"What's your name?" Bill said.
"Fellatia. Like fellatio?" he asked.
"Yes," I said smiling widely."Do you like fellatio?"
"I like giving and receiving it with a girl like you, Fellatia."
"That's hot, Bill," I said."You get right into talking about having oral sex with a girl you just met."
"The way you are dressed, would you expect me to think about anything else?" he said.
I modeled my bra and panties and stockings for him, twirling around like a lingerie model on a catwalk.
"Do you really like it?" I asked.
Bill smiled. "You're the only kind of girl I like," he said.
Suddenly feeling super sexy, I raised my arms above my head and said, "I'm really glad you came, my love. I've been wanting a man who likes me for who I am and not just because Sherry is so hot."
"Do you think she's hot?" said Bill."I don't think she's hot at all." He pointed at my black lace panties."I think what's hot is what you have down there in those little panties you're wearing."
I looked down at my soft little dickie hidden way down in my crotch under the see-through black lace material. No other man had ever mentioned it and I realized I was suddenly alone with a man who wanted me as much as men wanted Sherry. This gave me special feelings for Bill, right away.
I decided I was going to act like a southern belle with her handsome cavalier, tonight.
With a sweet southern belle voice, I said, "Can I get a drink for my handsome gentleman?"
He smiled. "A beer would be nice if you have one, my fair lady."
I was happy to hear he was willing to play along and be the Rhett to my Scarlett.
"I'll just be one moment, you big handsome boy."
I walked into the kitchen to get Bill a beer and I was suddenly aware that my dick was still soft in my little lace panties. Normally, it would be hard already from my panties rubbing against it. Somehow, tonight was going to be different. It was going to take a man to turn me on and not just panties.
As I returned to the living room with the beer for Bill, I suddenly felt naked in his presence. After I gave him the beer, I went into the bedroom to get a sexy little short robe of Sherry's that barely covered her ass from behind and showed off her sexy legs in front.
When I entered the bedroom, I saw that Sherry had already stripped Terry out of his clothes and was letting him play with her big tits. We didn't even look at one another as I went into the closet and put on her silky black robe.
Back in the living room, I sat down on the couch next to Bill and saw his eyes go down to my shaved legs. He reached out and put one hand on my thigh and started rubbing the soft inner part of it.
"You have nice legs, Fellatia," said Bill.
Acting shy and using my southern belle voice, I said, "Tch, I'm sure you say that to every girl who looks like me, Bill."
"No. I'm being honest," he said. "Your ass is really nice, too."
I batted my eyelashes and looked down shyly. "And why, may I ask, would you be looking at my ass?"
"I saw it when you were modeling your lingerie."
"That was beforeI knew I was with a real gentleman," I said. "Most of these young bucks that Sherry brings home don't know how to treat a lady."
"Oh, I know how to treat a lady," said Bill, squeezing my thigh suggestively when he did. "Ladies like you need to be treated tender and nice. That's how I want to treat you."
"And where, may I ask, did you learn to treat a lady like me like that?"
"I've been with lots of trannies and I know what they all like. They just want a man to love them like a woman. I'm sure I could have that love for you."
He moved closer to me and put his arm around me and we kissed for the first time, very tenderly with closed lips. As we did, he moved his hand further up my thigh toward my crotch. Suddenly, I felt like my panties had a pussy in them and I no longer had a dick. My little dickie was still not hard, but my heart was pounding hard from having a man treat me like a woman.
"Bill, darling," I said."Every man who comes here ends up wanting Sherry more than me. I'm so flattered to find a man who wants me more than her."
"If she had a cock, I'd probably like her, too. But she only has a pussy and I only go for girls with cocks.," said Bill.
Bill moved his hand further up my thigh toward my panties under the robe and I felt like he was ready to grab my cock and make it hard so he could suck on it. This cat and mouse game of sexual allurement was very enticing. I felt my little dick start to get excited down in my little lace panties and I didn't want to get hard for him, yet. Like a shy girl, I reached down and took his hand off my thigh and held it in both of my hands.
"Why, Bill, would you so mind if we got to know each other better before we do to each other what men and women like to do to each other so much?"
Bill smiled. "I'll be glad to take as long as you want, my lady."
"Thank you," I said as I placed his hand on his own thigh. "Would you be so kind as to hand me my glass of wine like a good boy?"
"Not at all, my dear."
Bill reached for my wine glass and picked up his beer in his other hand. I put my legs up under me on the couch and leaned toward him as he sat back down. Our heads were now just inches apart and when our eyes met, I felt a new connection I'd never felt with a man before. There were feelings stirring inside of me that had nothing to do with getting my cock wet, tonight. I wanted this man in a way I wasn't even sure of, yet.
He handed me my wine glass. "Thank you," I said.
"Sure," said Bill smiling. "It's nice to see you moved closer to me."
"I think I want to be close to you, all the time, Bill."
He smiled widely as he held up his beer to tap my wine glass in a toast. "Here's to being together, all the time," said Bill.
We tapped glasses and each took a sip as we stared at one another passionately. Then Bill took the glass from my hand and set it down with his beer. Without a word, he sat back down and put his arms around me and started kissing me fully on the lips, eventually opening his mouth and French kissing me very seductively.
When our lips parted, he said, "Damn, you're a beautiful woman, Fellatia. I bet all those other guys who were coming here didn't even notice it."
"But you do, is that right, Bill?"
"Of course, I do," he said."You have pretty eyes and skin and soft features. You were made to be a woman, my dear." He reached for my hand."Look how small your hands are, like a woman's. Look how skinny your wrists are. You're perfect as a woman."
Suddenly, all the sexual escapades I had with Sherry seemed wrong. I realized I was only fucking her ten times a day because she wanted it. Now, she had another guy who could fuck her all night and she was just as happy. But I was needing more and Bill was teaching me it.
"I think I would enjoy living with a man as a woman," I said. "Would you be such a man, Bill?"
"Oh, honey, that's what I've wanted for years," said Bill. "Do you know how many nights I fall asleep stroking my cock and dreaming about having a woman like you?"
I smiled as I reached down between his legs and squeezed his semi-erect cock through his pants.
"You mean this cock, right here, baby?"
"That's the cock," said Bill smiling.
I leaned toward him as I continued squeezing it. "I think I'd like to fall asleep stroking your cock every night, darling Bill."
He smiled widely. "What about your girlfriend, Sherry?"
"I think she'll be fine stroking Terry's cock, instead. I really want a man, myself, and you're helping me realize it, darling," I said. "I think I want to suck your cock, right now, for you, babe. And I'm going to do it for you so good you're never going to want another woman to do it for you again."
I got down on the floor in front of Bill and unbuckled his belt and unbuttoned his pants and pulled down the zipper. He kicked off his loafers as I pulled down his slacks and left him sitting on the couch in just his boxers as I got up and hung his pants over a the back of a dining room chair to keep them from wrinkling.
Having a handsome man who really seemed to have feelings for me sitting on my couch in just his boxer shorts was thrilling to me. But still my little dickie was not getting hard like it normally did in my sexy black lace panties. I made sure Bill got a nice view of my ass cheeks hanging out under Sherry's short robe while I hung his pants on the chair.
I was happy to see he had a boner when I returned to the couch. "Why, Bill," I said, "is that big beautiful boner just for me?" I was smiling as I looked down at the perfectly-shaped love muscle poking up out of his boxer shorts.
He laughed. "Looking at your behind gave me this," he said.
"Why, I bet you say that to every woman."
"No, I'm serious," he said. "Your ass is really nice."
"Now, you're making me feel shy, you big boner boy,"I said. "What if every man liked my ass as much as you do? How could I ever resist all those big boners they wanted to give me?"
Bill laughed."You need to cover your ass when you're not with me, darling. Otherwise, lots of other men will want that ass of yours."
I laughed. "Surely, you jest. You must be kidding me, you big handsome boy."
"Haven't other men told you what a nice ass you have?"
Shyly, I said, "Well, they have. But I thought they just told me that to be nice."
"No, darling," said Bill. "I'm sure every man who sees your ass would like to screw you in it, even the straight ones."
"Well," I said smiling. "I have had straight men fuck me in it. But I thought they were just being nice to me because I wanted to feel them inside me. It never occurred to me that they wanted me like a woman."
"I'm sure there's a lot of things about your sexuality you don't understand, yet," said Bill. "You probably don't know that you could have just about any man you wanted if you went to a gay resort like Key West or Provincetown, Massachusetts."
"You mean, there's places where a girl like me can go and turn on men the way Sherry does with her body?"
Bill laughed. "Yes. They have strip contests and I bet you'd win ."
"The only thing I want to win, tonight, is you, Bill."
I loosened the belt on the robe and let it fall on the floor behind me. Hearing from Bill how desirable men would consider my body to be was teaching me a lot. In his view, I was too good for the drunken men Sherry brought home from the bar for me who really just wanted to put their dicks in her over-worked little pussy. I was as sexy and desirable to men as she was. The thought never occurred to me, until now.
There I was standing in front of Bill wearing black lace panties and a bra and silky stockings and I was what he wanted most. I suddenly remembered that first night with Curt when Sherry had left the room and we had really gotten into fucking each other good. Curt said he had fucked the quarterback on his football team before, so he knew a man's ass could give him pleasure like a woman's pussy. Now, I was coming to learn it, too.
I was sexy and desirable and ready to please any man who came my way, anytime, just like a woman does. I was no longer the slutty girl looking for cheap sex with a man, I was the mature woman ready to commit to a relationship with a man who understood me. That is what Bill was.
I moved closer to him and and he reached out and felt the insides of my soft thighs at the top of my black silky stockings just below my lace panties. I felt just like a sexy girl ready to get some hard cock, tonight.
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