Stephanie and Brandi

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Stephanie has a night with Brandi and her boyfriend.
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moonsissy
moonsissy
247 Followers

*This story is based on a real event, though some of this is also very fictional.*

I met Brandi on an adult website. She was in her late 30's and recently divorced. She was so attractive, with shoulder length blond hair, a hot body and pretty face. She had mentioned on her profile that she liked powerful men who were well endowed. Very much the opposite of me. I was fem and small in the penis department (maybe I should say very small). But she was looking to meet a bisexual guy, crossdresser or transgender woman. She loved seeing guys having sex. She especially loved when an alpha was in control of a beta. I was certainly a beta.

It was a nice surprise when I received a reply from her. She said she thought I was so pretty and loved my eyes. So we started chatting on line. Then we started texting and then we made plans to meet.

The first time we got together Brandi wanted me to be dressed as a guy. We would meet for dinner. If we connected then we'd go back to my place where she would do my makeup and get me ready to go out dancing at a local club.

We met at a busy restaurant in town and she was dress in a sexy peach dress and I loved the cream colored pumps she was wearing. They went fabulously with her dress. She was tall with long shapely legs. She kissed me on the check and said, "Oh, wow. Your eyes are so beautiful, even without makeup. I think we are going to have some fun together."

I had to agree.

As we ate dinner she went right into calling me "Stephanie" and "girl" even though I was dressed like a guy. When the waitress came to the table for our order, Brandi said, "What are you going to have, Stephanie?"

I hesitated and told Brandi. She looked at the waitress and said, "She'll have the chef's salad and I'll have the chicken special."

I was a bit embarrassed about her referring to me in female terms. It's a small town and I was worried someone I knew might overhear in this crowded room. But as embarrassing as it may have seemed it was also titillating. I felt myself getting aroused every time she feminized me in our conversation.

When we finished dinner she followed me back to my place. We went right to my bedroom.

"Take off your clothes Stephanie. You're done with looking like a guy," Brandi said as she smiled at me. "Not that you look much like a man anyway."

I gladly took off my clothes and stood there in a bra, and panties.

"Well, don't you look sexy already. Such a fem bod, and so smooth. We are really going to enjoy what I have planned tonight." She ran her fingers over my shoulders and gave me a short but sexy kiss.

She told me to sit on the edge of the bed. She had brought a bag with her. She reached in and pulled out some black fishnet stockings and said, "Here, put these on."

She saw my makeup sitting on the dresser waiting patiently for us. She picked up a bottle and started to transform me. She smoothed on some liquid foundation and said, "when we are done with your makeup those wonderful eyes will be shining brighter than ever." I was feeling flutters in my stomach. This woman was turning me into a beautiful butterfly and it thrilled me.

As she continued with my makeover I realized I had an erection in my panties. Then she must have seen the little bulge as well. She smiled and said, "Looks like someones aroused. Obviously being changed into a girl turns you on."

Brandi reached down and pulled back the top of my panties. My excited little thing popped out.

"Oh so pretty," she said, "smaller than I am used to seeing but it's so cute. when I'm done with your makeup I will take care of that for you."

Brandi, created splendor on my eyes, than ran the lipstick over my lips as if she were an artist. When she put the lipstick down, she got on her knees in front of me. She pulled my panties down and took my tiny dick between two fingers and started to stroke me. I moaned softly. She reached up and slid her hand into my bra and started playing with one of my nipples as she played with my dick.

"This little clit is so hard. Are you going to cum for me?" she asked as her fingers moved slowly up and down.

"Oh god, yes," I answered. She lowered her head and took me in her mouth and in less than a minute I was having a spectacular orgasm. She kept me in her mouth until I was done shooting my cum. She got up and started to kiss me and feed me my own sperm. It tasted so good as I swallowed it. Her tongue slipped deeper into my mouth.

"You have such a small dick hon, but you have such sweet cream, " she said when our lips separated. "I ended up swallowing some myself but I wanted to share it with you." She paused for a moment and then continued, "You know, that is the smallest dick I have ever sucked. I usually go for men with big cocks. You'll get to see that first hand as we get to know each other. But before we do anything else, you need to repay the favor. I am so aroused right now. I need to cum. Your little dick is to small to get it done so on your knees girl."

I knew she liked big cocks, and I knew I was tiny by any standard. She liked alpha males and I was so far from that that it was comical to think otherwise. I knew I wouldn't be fucking her with my little dick. None of this bothered me, though. I knew I was there for her fantasies. They were my fantasies too. I was there getting what I wanted too. This beautiful, sexy woman had just given me a blow job and now I was licking her pussy and soon she would be sharing strong, sexy men with me. She'll watch as these masculine hunks dominated me, and I will gladly eat cream pies from her pussy.

Brandi pulled her dress up over her hips and slid off her panties. She sat on the edge of the bed and spread her legs. Her pussy was open slightly and already wet. I got down in front of her and softly danced my tongue over her clit and slipped into her wet folds. She put her hands on my head and held me there. I slipped two of my fingers into her and licked and lapped at her sweetness.

"That's it baby," she moaned, "Keep that up, right there...oh yes Stephanie, fuck yes!"

She began to orgasm as she pulled me into her. She moaned loudly and I loved that I was able to give her such pleasure. She laid back on the bed for a minute or two, slowly regaining her energy.

"That's the way to start the night babe," she said as she sat up, "I bet you learned to eat pussy while eating cream pies. You like eating cum from pussy?"

I smiled and nodded in the affirmative.

She had no problem talking about sex. I liked that a lot about her.

"Did you suck cock or eat pussy first?" She asked.

"The first sex I had was with a woman," I replied almost defensively, as if to prove I did like sex with women.

"That's not what I asked. Don't be shy. We both know you are a cocksucker, Steph. That's why you're here."

"I sucked cock first. I was about 20."

So how did it happen?"

"I was at this outdoor party. It got late and I was a bit drunk. I was real horny, but all the girls were coupled up or gone by the end of the night. I was about to leave when this guy came over and started talking to me. I had noticed him earlier. He was big, like 6'3" or something. And I couldn't help but wonder to myself if his dick was big, too. When I first saw him was he was with the only black guy at the party. I found out later they were college athletes and teammates."

"They weren't with girls?"

"No. His girlfriend was away and he came to the party looking to find some sex. But he told me all the girls that were there knew his girlfriend and he didn't want to chance it. Anyway as we talked I realized I had a hard-on. Something about his energy. He was so masculine and it made me feel, I don't know, like un-masculine I guess. It didn't help that I was wearing eyeliner and my hair was long. Luckily I was wearing tight panties that kept my erection pulled close to me. So I was sure he couldn't see my little bulge. He was telling me he was hoping to get a blow job but all the girls were gone. He told me he had a raging hard-on and said if I wanted to see it I could just look down at his pants. He said he had a really big dick so obviously I couldn't miss it. I looked down, and unlike my pants, his were sticking out. He asked if I minded if he freed his cock because it was hurting being so restricted."

Brandi laughed, "what a line!"

"Yeah but you know, I didn't mind. I wanted to see a big cock in person. He opened up his pants, and there it was, standing straight up and calling to me. Even in the dark I could see it's powerful thickness, it's raised veins, and cut head. He knew I was staring at it and said, 'I told you it was big. Want to touch it?' I never touched another guy's cock before. I was almost shaking. He stepped closer and told me, 'go ahead. You know you want to.' So I reached out and touched it. It was thick and hard, yet soft. It was so big compared to my own. I thought 'how could I compete in the sexual arena when there are men with penises like this?'

"My thoughts were interrupted when I heard him tell me to suck on it. I dropped to my knees as if my brain were programmed for this. I wanted that dick so much. I looked up at him and he nodded his head. I opened my mouth and took that big dick between my lips and I was more aroused than I'd ever been. At that moment I became a cocksucker.

"He said, 'I knew you were a cocksucker the minute I saw you. I told my friend if we didn't get lucky with the girls that we'd get our cocks sucked off by you. He actually thought you were a flat chested girl when I pointed you out.' He put his hands on the back of my head and started to fuck my mouth. I opened as wide as I could so not to use my teeth. He was gagging me with his big dick and I was slobbering all over it. I couldn't breathe at times which I hadn't expected. It scared me at first but also excited me to be completely controlled by this masculine hunk of muscle."

"Oh my god, Steph, that is so hot," Brandi said as she started rubbing her clit in front of me.

"It got even hotter. As I was being face fucked by that big dick his friend called out looking for him. He said, 'I'm over here.' I wanted to stop sucking. I didn't want anyone seeing me like this, but his strong hands kept my head in place. I heard his friend walk over and then his friend said, 'Fuck, isn't that the skinny flat chested sissy you pointed out earlier? You called it right. You knew she was a cocksucker.' And with that I could hear him undo his belt buckle and zipper. He stepped close and started slapping my face with his dick. The guy fucking my face released my head and offered my mouth to his friend. I looked up to see this big black cock waiting for my mouth. I opened wide and there I was sucking another dick. Two in one night. My first time ever sucking dick and I get to suck two."

"That is wild! Did they cum in your mouth?"

"They kept switching back and forth using my mouth for their enjoyment. I would stroke one while the other was thrusting down my throat. I couldn't tell you who had a bigger cock but I can tell you I loved them both. It felt so natural for me to be pleasuring their dicks. I was so turned on as the talked to each other about me, as if I was an inanimate object. They were calling me 'the cocksucker' or 'this cock whore' or 'the flat chested bitch.' And eventually the guy I started with was in my mouth and I felt a change. He held my head tight and said 'I'm coming bitch.' And all of a sudden I was feeling and tasting his warm sperm fill my mouth. The black guy had taken his own cock in hand and was stroking furiously as he watched. I heard him say 'that's it fill that slut with cum.' And no sooner did the first guy pull out then the second guy grabbed my hair, pulled my head towards him and shoved his big black cock down my throat, just in time to shoot his seed. I swallowed all of it. I felt like a little slut. And I liked that feeling. I was on my knees with cum in my belly and some still in my mouth and some dribbling down my chin. I watched as they pulled up their pants and high-fived each other. Then they just left me their on my knees in the grass."

Brandi was now arching her back and I thought she was going to have another orgasm, but she stopped just at the edge, "That was so hot I thought I'd cum, but I better hold off for later." She giggled. "What did you do once they left? I bet you jerked off."

"Oh yeah. I just reached into my pants and started to rub myself and came in my panties in like 10 seconds. I was just so aroused."

Brandi finally arose from the bed, straightened her dress and went to her bag. She pulled out a pearl necklace. "Put this on. It's just costume jewelry but it is symbolic. That story was so hot. I can't wait to see you with another guy." She then handed me little pearl earrings.

I got dressed in a little black mini dress, and high heels. We touched up our makeup which had gotten a bit messed in our oral exchange. When we were ready Brandi took me by the arm and we strutted out to her car. We were two women off to have some adventure.

"We're going to skip the dancing hon," Brandi said as we drove in her car. We have a date with a boyfriend of mine. You are going to love Ronnie. He has such a hot body and he has a lot of stamina. And just to let you know, when he's ready to cum, he always does it on my face. In this case I'm sure it will be on both of our faces. And he unleashes a large pool of sperm. And I do mean a large pool."

When we arrived at Ronnie's we pulled into his driveway. He had already opened his door and we strutted right up to him in our mini-dresses and our fuck-me-pumps. He pulled Brandi close and started lustfully kissing her. When they stopped she said, "Ronnie this is Stephanie. She can't wait to see your big dick. I've told her so much about it."

Ronnie smile and invited us in. No sooner did he close the door than he turned to me and said, "Why don't you be a good girl and act like my fluffer. Get me good and hard and ready to fuck you two."

He quickly dropped his pants to the floor and there was this handsome cock swinging between his legs. It wasn't even hard yet but it was still hanging down at 5 or more inches. Bigger than I was when I was fully erect. I dropped to my knees, like always. I took his flaccid pole in my hand and took it all into my mouth.

"Oh that is so hot," Brandi moaned. She started petting my head, "she's all bottom and very submissive. You are going to enjoy using her." She said to Ronnie.

They started to kiss as I did what cocksuckers do. I felt him starting to get stiffer and fatter. As the two of them kissed passionately I made love to that cock. I licked, kissed and sucked it into my throat. Brandi was petting my hair and he put one hand on the back of my head.

He started to thrust and fuck my mouth. I could see their tongues darting between their lips. I felt so possessed with lust. My little erection was snug in my panties.

When they broke their kiss he pulled out of my mouth. He took Brandi by the hand and led her to the bedroom. I got off my knees and followed. He laid her on the bed. She spread her legs and I could see his hard erect penis start to slowly enter her.

Brandi looked at me and said, "dance for me Steph. Take off your dress. Let me see your little clit."

I did as I was told. She watched me and stared into my eyes as he fucked her. I slowly and seductively danced for her. She started to orgasm. She was screaming and thrusting her hips. He was thrusting and breathing heavy. She came and it seemed to go on and on. Her eyes connected to mine. I swung my hips back and forth and let my little dick swing free. I had my panties pulled down and tucked under my little balls. She then gestured for me to cum closer. I got right up to her face and she began to suck on my tiny erection. After a few seconds she began to have another orgasm.

After she had calmed down, Ronnie pulled out of her. He went to his dresser and got a jar of lube.

"Pull your panties down, Stephanie and bend over the bed," Ronnie told me.

I slipped out of my panties, bent over the bed and spread my legs. Brandi had sat up in bed.

"Oh Steph I can't wait to watch you get fucked like a fem girl should be fucked," she said as Ronnie grabbed my hips.

I had been lusting for this. He started slowly. First there was one or two inches then he'd pull back and each time he gave a little thrust he went further. Oh, the pain and the pleasure. Soon though he was in balls deep. He had lubed me up well. Then he started fucking me. My ass was in the air my face was buried in the bed. Brandi was moaning as much as me. He slapped my ass, called me slut and asked if I liked it.

"Fuck, yes! I love it. Don't stop please, Fuck me hard. I want your big cock so much." I was moaning and screaming and I knew I was going to orgasm any second. I loved to orgasm this way with a hard cock inside me hitting my prostate in just the right way.

"That's it baby cum for us," Brandi said as she started to touch my body.

She reached into my bra and took a nipple in her fingers and this sent me over the edge. I began to scream in high pitched girly squeals as I came.

Ronnie continued to pound my ass and Brandi positioned herself so I could lick her pussy. I tried my best to lap her wet clit and fuck her with my tongue. I was beginning to feel weak from the orgasm but I wanted her to cum. I wanted him to cum too but not too fast. Even though I'd already cum I was enjoying the feel of his big dick filling me up.

"Oh fuck, Steph, you are going to make me cum again," Brandi moaned. Her hands were on my head, his were holding my hips. He was hitting all the right spots and I was shocked to feel myself having another orgasm. I started to scream but my mouth was smashed against her pussy and she started to scream. We came together.

Ronnie quickly pulled out of me and told me to lay next to Brandi with our heads close together. He was stroking that big dick. I weakly got on the bed and put my face next to hers. Ronnie stood on the bed towering over us, one hand on the wall the other furiously stroking himself and then it started. Streams of thick seed began hitting my face, then Brandi's. He was moving his hose back and forth and the sperm was flying all over our faces and into our hair. It was running off my cheeks, my chin and my forehead. I opened my mouth to catch what I could. After what had seemed like minutes of cream raining down on us, Ronnie knelt down on the bed. Brandi turned her face towards mine and started kissing me. I could taste Ronnie's cum on her tongue and lips. She started licking my chin and we started licking all the cum off of each others faces and kissing.

"It's nice having two cum sluts in my bed," Ronnie said as he watched us devour his seed, "We'll have to do this again."

moonsissy
moonsissy
247 Followers
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BiCowboyDFWBiCowboyDFW15 minutes ago

Mmmmmmm YUM. More please!!!

AnonymousAnonymous8 months ago

One of the best stories I've read. Love to hear sissies referred to as girls, makes them so much more submissive.

AnonymousAnonymous8 months ago

One of the best stories I've read. Love to hear sissies referred to as girls, makes them so much more submissive.

AnonymousAnonymousover 1 year ago

Absolutely wonderful story! Thank you for sharing!

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