Sissy Whisperer

It has been several months since I broke up with my girlfriend, more like she dumped me. She said there was no passion and life was too short to waste her 20s on me. It hurt, but she was right, I wasn't very aggressive or requested to engage in sex often enough. In fact, she would often try to show she was horny by telling me things during the day or wearing something sexy and most of the time I'd say I was too tired for it.

After that, I basically concentrated on my college work and tried to ignore how hurtful it was to be dumped like that. Luckily, I had a friend Keri, from High School in many of the same classes since we were both in the nursing program. We didn't hang out much in High School, but after graduation, most of our friends moved on and we were like the last two to be picked for dodge ball.

After my break-up, I started to hang out with her at school and I eventually explained what happened with my ex-girlfriend. She was way out of my league and frankly, after my last break up, I was just happy to be able to hang out with her sometimes.

Keri had a job at the local adult store, and she always tried to get me to stop by, but I was too shy, introverted and a bit of a sexual introvert as well. She would share fairly detailed stories and I admit, sometimes, I found myself getting excited and I would request she change the subject. She would tease me that if I ever allowed myself to loosen up a little, I'd probably enjoy life more.

Sometimes when we hung out after school to study at either her place or mine, she would bring a bag of goodies after work. Typically, it was damaged packaged items. She was always excited to share her bag of goodies which varied from flavored lube, edible panties, dick shaped candies, pornos, lingerie and of course toys. She liked to dare me to try things like hold a big dildo, guess the flavor of lube or edible panties, or try on a wig. One time after a beer, I ate penis shape candy and joked, "I just ate a dick." I was lightly buzzed, just enough to loosen up a little and Keri laughed at my joke.

I have always felt a little confused with sexual thoughts and they varied beyond typical guy and girl sexual relations. I just assumed being raised catholic that I was being tempted by evil, even though I really didn't fully believe in the things I was taught growing up. I couldn't talk about it with my last girlfriend; she was more about getting what she wanted and didn't really want to talk about things that didn't involve improving her life. Anytime I vented about school, she would turn the conversation to something she was dealing with. Even though Keri and I were close, it didn't feel like it was something I could share with a friend.

One Friday after a big set of exams, Keri made plans to hang out at my apartment and she would bring beer. We were both in need of some stress relief after a brutal set of exams and I wasn't comfortable going to the bar with many others from school. So, she came up with the idea to hang out at my house and just drink and maybe binge a show or watch some movies.

I heard a knock at my door, and I opened it to her grinning first showing me a 12 back of beer and a bag of goodies from work. "Holly Hell Keri, are there more people coming, I'm a 3-4 max drinker." I said sort of greeting her and slightly ungrateful on her offering of beer.

"I know you are lightweight. Literally, but you need this probably more than I do." She said as she walked in by me. I closed the door and followed her to the kitchen. She said the beer is pre-chilled and after grabbing bottles, she put the rest in the fridge. We hung out in the kitchen for a few minutes and talked about the exams and complained about how hard they were. Then she announced, "No more school talk." Then held up the bag, "We need a break from that stress, and I know you need a break from stressing out about other things." She knew I was a little off since the breakup, but knew I didn't want to talk about it. "Follow me and bring two beers with you."

She headed to the living room with the bag and her beer. "But you already have a beer."

"Both of those are for you." She said as she placed the bag on the coffee table. She took her typical seat at the left end of the couch, and I took mine at the other end. She looked over at me, "I promise, if you try everything in this bag tonight, you will feel a lot better, maybe even ecstatic."

I raised an eyebrow questioning her promise. She knows I always say no to 98% of the stuff in bag of freebies. I was hesitant, but I was mentally drained from the tests and really didn't feel like being a heel tonight. It was just me and her, it couldn't be too embarrassing to watch some porn, touch a dildo and taste some lube. So, I clinked her beer and said "I'm in."

She beamed, bounced a little and reached into the bag to pull out a DVD. I couldn't see the cover and after she took it out of the case, she placed the case back in the bag, walked over to the PlayStation and slid it in. I began drinking my beer knowing I was going to need some liquid courage to watch a porno with my hot friend that had no inkling of interest in me.

I then sat up to see what was in the bag and she turned around. "No peeking you curious monkey." She slapped my hand, then picked up the controller to start the feature presentation. "Before I start this, I'll give you 3 guesses on what it is. If you don't guess right, down your beer. If you do guess right, I down my beer."

I could tell, I wasn't going to guess right, and I started to drink my beer while trying to think of what crazy stuff she brought that likely would make me feel embarrassed and uncomfortable. "German Bondage kitties."

She almost spit her sip of beer. "No. Try again genius."

"Two girls, one cup." I said as I drank my beer.

She laughed again, "Gross and no. You aren't trying, think of typically porn genres like Milfs, lesbians, anal, etc."

"It would be easier if it were multiple choice." I said.

"So would have the exams, quit bitching. You got one more shot." She said then sipped her beer.

She had a look that was pure confidence. She knew I wouldn't guess what it was, but I gave it one last shot. "Gangbang Cosplay."

"Ok, that was better and a little surprising, but nope. Bottoms up bitch." She said smiling.

After the bottoms up comment, I replied, "I knew I should have guessed Anal." Then I started to drink up.

She laughed and picked up the controller. She wouldn't start the porno until my bottle was empty. I belched as politely as possible, showed her the bottle was empty. She smiled and started the movie. After the federal warnings, the next screen, 'Versatile BBC.' I heard the 'BBC' before, but I was 60% sure it was a texting thing or 40% sure it was a sex thing, so I never tried to use the term. I was raised to fear using the internet, so I rarely used it to learn about things that I would be afraid to mention in a confessional.

Keri sat up with legs up by her chest, slipping her beer. The first scene opened to a muscular black man sitting on his couch watching tv wearing just jeans and boots on. Shortly, he calls for someone and a cute blonde, white girl comes in wearing black lingerie, consisting of a body suit, garters with stockings. She had a collar and leash and sported high heels. She stopped in front of him and knelt by his left leg and handed him her leash. in front of him. She looked up at him waiting for his next command. He simply pointed at his crotch, and she started to remove his boots, one at a time and placed them neatly next to the couch. Then she sat up a little to undo his jeans and he lifted up enough for her to help take his jeans off. He was wearing boxer briefs and the bulge looked like he robbed a nearby deli. She rolled them down enough to reveal his package and I gasped. Keri responded, "I know right?"

I started to drink more thinking this is going to get intense and a bit arousing. Alcohol helps lower my libido, but it also inhibits my brain to mouth filter. I've always been mindful to not say any of my deep thoughts. I hated being picked on when I was younger and learned quickly that boys are to be boys and girls are to be girls. That's rule one of life.

Back to the porno, the sexy woman then took one hand to lift it up. It wasn't hard, but it was still huge and looked like a radiator hose. She sat up a little to let it rest across the top of head and the camera moved to give a close up of her with a big black cock resting across her blonde hair almost touching her far ear. I now knew what BBC meant. "Big Black Cock."

"It sure is." Keri said staring at the screen. I realized my mental filter is compromised, but I needed to keep drinking to get through this. I didn't want to feel uncomfortable the rest of the night.

The hot woman on screen proceeded to worship his cock with her hands, kissing and licking the head and up and down the shaft as it got bigger and harder. She then centered up to it, eye to eyes with it, leaned in and placed her red lips over the head of his cock. It was so big; it was like she was trying to blow a tall boy beer can. I've never seen anything like that, it was impressive and emasculating at the same time. I was nowhere near that big. I was more of a facing the wall in the locker room shower type of guy.

Keri would sneak a peak at me from time to time to gauge my reaction. As I finished my second beer, she noticed, got up and took my empty bottles to the kitchen returning with two new beers. The lovely enthusiastic girl was still blowing the guy's pole and he would push her head down the shaft until she gagged and repeated until she had at least 8" in her throat while still having 4" from her nose to his belly. Then he pushed her off, twirled his finger and she stood up, turned around, unsnap the crotch of her bodysuit and using a hand on each thigh, she began to sit down on his lap while he lined up the pole to her glistening pussy. Her head tilted back a little as it started to enter her. Her long hair just touching his rock-hard abs and her eyes rolled back while moaning. He grabbed her hips and began to motion her up and down. She was clearly enjoying it, smiling, then biting her lip, and shifting her hair from side to side. This went on for a few minutes and I was just astonished. Size really does matter.

Then they changed positions and she got on her hands and knees on a shaggy white carpet. She wiggled her cute ass, and he knelt behind her, slapped her ass making her beg for it. After he was satisfied with her begging, he guided his black salami to her eager vagina. He started slowly, but then became more aggressive and she seemed to be enjoying it even more. His thrusts were forceful and powerful. She couldn't stay up on her hands anymore and fell to her shoulders and reached her hands back to her butt. He grabbed her hands and used them as leverage to really force every bit of his cock into her.

I could feel myself getting turned on and was concerned Keri would notice. Placing a pillow on my lap would be too obvious, leaning forward would show I was eagerly enjoying it, so I just lifted on leg up to my chest. Keri noticed but didn't say anything.

After several more minutes, he gave her three really hard thrusts. His cute gluteal muscles flexed, then on the last thrust he grunted and pulled her as tight as possible. As he pulled out, gobs of cum dripped from her and she was panting so hard on the verge of passing out or orgasm. I wasn't sure, my ex-girlfriend never responded to sex like that. The scene ends and Keri pauses the video and runs to bathroom to pee.

She came back, gave me another beer. "Finish that one before I start the next scene." She returned to her spot on the couch.

"Thanks, I need another one after that." I said, then drank the rest of my beer.

She laughed, "That was mouthwatering. Right? I always feel a little tingly after watching BCC. How about you?"

Remember your inner filter is compromised. Don't respond, just drink you moron. "I wonder what it's like." I said before I even got the bottle to my lips. Damn it.

"Me too. I've never been with anyone that big. It looks hot. I always imagine it's like the best mix of pleasure and pain." She picked up the controller and continued the video.

That was close, she hopefully thinks I was thinking I wanted to know what it would be like to have a cock that big and not what it would be like to be her.

The next scene was another big black guy and a white couple in a bedroom. All three were in their underwear with the woman and the black guy making out on the bed while the white guy sat in a chair watching them. She was enjoying herself and even the boyfriend or husband was rubbing his crotch. She then moved down to start oral on him and he laid back resting his head on the pillow letting her do what she is was good at. After she was satisfied, he was at full mast, she moved up to sit on his massive pole bracing herself on his muscular chest. The guy in the chair was starting to jerk off slowly.

After she was fully satisfied from riding him, she got off, turned around and did reverse cowgirl for a few minutes. She would smile and wink at the guy in the chair. After that, he had her lie on her back, pushed her legs to her shoulders with her feet pointing to the ceiling. That was the final position for him to get his rocks off. After a few minutes, he made his finishing climaxing moves. Her legs shock and she couldn't even make a sound from the orgasm she was experiencing. He fell on top of her. She was bearing his weight but didn't seem to mind. She was still euphoric from her orgasm. Then he dismounted her and left the room.

After she recovered from the titillating experience, she motioned to the guy in the chair with her finger to come to her. He stopped touching himself and came over to her. The camera showed his point of view of her spent vagina dripping with the big guy's seed. Without hesitating, he licked her and lapped up all the cum and juices with his eager mouth. As he leaned over, you could see he had a butt plug in his ass. The title of the scene was 'BBC and cuckold.' So, I learned another sexual term. Two in one day, I feel so educated.

Keri paused the porno, and I took the opportunity for the intermission to go pee. She wanted to know what I thought about the second scene, but I had to hold up a finger to signal 'give me a minute' and I walked to the bathroom. I was still in the mid stages of an erection, but soft enough to wiz. I noticed a wet spot on my undies too, it was pre-cum. I never did that without being fully erect before. I cleaned up, positioned my little guy so that if I could hard it would grow along my groin and wouldn't be noticeable. I washed my hands and went back to the living room. When I got back there were some clothes folded on the sofa. It looked like two small piles of white and pink. I didn't think much about it and sat back in my spot.

"So did you have to shoot one in the sink after that one?" Keri said and I hoped she was joking.

I was a little shocked by the brash question, but answered, "No, I had to pee, JUST pee." That seemed a little too much, like I was hiding something. I was buzzed and I could feel my eyes moving a little slower, I was clearly at max buzz. My body fat was still really low from being a triathlete. It didn't take much to get me drunk. I knew I would say what I was thinking, but didn't really care anymore, "I think it made me wet."

Her eyes widen, "Really, wow, that is hot. So, you like it so far?" I just nodded my head in affirmation. She then looked at my beer, "Hey prom queen, looks like your beer is getting warm. Bottoms up." Then she picked up a set of clothes and went to the bathroom. "Be right back and that better be empty when I return."

While she was gone, I worked on the beer and thought of baseball to get things to reverse course down there. As I finished and placed the bottle down on the coffee table, I looked at the pile of clothes she left. Before I could inspect them more, she was back and handed me a fresh beer. She looked amazing. She changed into short pink booty shorts and I white tank with 'Daddy's Girl' across her boobs. She did a little model pose for me. My jaw must have been in my lap. "I take it you like it?"

"Wow, ya. You look amazing." I said just staring at her like an idiot. "Is that your uniform for the Store?"

She laughed, "No, I get to wear normal clothes when I work there. If I did wear this, I think it would boost business a bit." She then picked up the other set of clothes and handed them to me, "Your turn. For this last scene, we are going to do something a little different. Think of it as cosplay."

I looked down and noticed that it looked like the same things she was wearing. My first thought wasn't I can't wear girls' clothes, it was "But, I won't look as hot as you." Crap, before I finished my thought, it was already on its way out.

She quickly replied, "You will look great, trust me. With your thin body, long hair, you will make a cute brunet."

With that vote of confidence, I got up and went to the bedroom to change. As I took off my undies, I had a sting of precum, and the wet spot was larger than before. When I slid pink the shorts up, they were low on my hips and provided very little room for my junk. If I got any harder, it would peek out the top of the shorts. I decided to tuck my junk. Every guy has at some point, or at least that is what I told myself when I would do it from time to time. I then pulled up the shorts the rest of the way and they fit much better. I then pulled the tank over my head. It was short about left about 6" of my tummy exposed. I then did a couple of rocker head bangs to loosen up my hair. The closet mirror was just a head turn away and when I looked over my shoulder, I saw the side of a cute girl with a cute butt. I looked cute, not passable, but with a little makeup, some heels, I think I could look hot. In fact, I thought, as dude me, I'd droll over seeing a hotty like me and would be too intimidated to hit on me/her.

I took a deep breath, opened the door, and walked out to the living room. With my blood fully inebriated, I was loosening up enough and actually felt myself sashaying a little. I didn't look at Keri at first. I walked past her to sit down, and she smacked my ass, "Good game." I jumped and stopped walking. She grabbed my hand. "Turn around, I want to get a good look at Daddy's Girl." I turned around, her eyes scanned me from head to toe. She smiled, stood up, placed her hands on my hips. "You look amazing." Then gave me a soft kiss. She stepped back, I was wishing for more kissing and had my head reaching out for her, but that was it, just a little kiss. She looked down at my crotch. "Did....did you...where are your bits?"

"I.. uh, the shorts didn't fit right, so I kind of tucked it." I said looking down bashfully.

She lifted my chin, "Daddy's Girl isn't bashfully. Chin up, own it, you look hot. Be the little hotty I know you can be." She then grabbed my hand, pulled me down to sit shoulder to shoulder with her. She handed me my beer, "Bottoms up girl." I began to drink it even though I was already beyond my limit. She then reached for the controller and started the third scene from the DVD.

It started with a cute girl wearing the same outfit that we were in. She had tiny titties like me too. "Hey, that's what I'm wearing."

Keri chuckled, "SHE sure is. She is hot too, right?"

"Yes, very. I'd never have a shot with girl like that." I said.

Keri giggled a little, "Ahhh, you shouldn't be so hard on yourself."

The girl in the video also had on white High heel platform heels. She had her legs crossed while flicking her hanging foot and talking on her cell phone. She seemed happy about the response to her request for her Daddy to come over. Shortly, the doorbell rings and she hopped to her feet, trotted to the door and guess who. "Ohh' I know, I know. A Big Hunky Black guy." I spoke.