My First Girlfriend Vol.5 free porn video

Chapter 12: Gurlfriend
As soon as I stopped shaking, she cleaned my crotch with a wet wipe, and started to reassemble the chastity cage. Believe it or not, I wasn't even that bothered by it this time. My dick was so completely spent that I didn't want to think about using it for anything the rest of the day anyway. I was more so just disappointed in myself for losing the bet. I felt like I wasn't meeting Rebecca's expectations of me sexually. Then again she didn't seem disappointed in me at all, so I guess I can keep compensating for my sexual inadequacies by being a sweet and obedient partner. She seems to like those things about me. She uncuffed my hands and I just about fell into her arms. I immediately pulled her panties from my mouth, though I didn't have anything to say. I was speechless after that kinky experience. She gave me a nice big hug and kissed my cheek, whispering playful taunts in my ear about how what a cute little slave I am. She asked if I enjoyed our little game, and I told her I really did although I was sad we wouldn't be having any sex this weekend.
"Don't worry sweetheart, you'll get other chances to fuck me when the time is right" she stroked my head as she reassured me. This woman was such a strange combination of caring and cruel. I was hopelessly under her thumb. I stumbled to the bed and flopped down. I needed a minute to catch my breath and cool down. Rebecca encouraged me to relax while she assembled my outfit for the day. I lay and watched her pick up the panties that had been in my mouth and put them back on. It seemed fitting that she'd have my drool adorn her ass and pussy. She waltzed around her room from closet to dresser pulling out stockings, a skirt, a bra, a couple tops, and a few other little accessories. She brought her little selection over to the bed and told me to get dressed. I started by putting my pink panties back on, followed by a pair of opaque black thigh-high stockings. The skirt she provided me was a very short, red, plaid one - classic slutty school girl. When I put it on it barely went down passed my butt. I felt very dirty and objectified already. Next, I put on the white training bra, and a tight white polo T shirt. I buttoned up the collar all the way to look nice and proper, waiting to be corrupted. There was also a little rubber bracelet that said 'bad girl' on it, which I assumed was meant for my wrist. The only thing left was a hair clip with a fake flower on it. I'd never put one of these in my shaggy mop-top, so I asked my Love to assist me. She kindly obliged, collecting my long bangs and fastening them over my ear - putting my face proudly on display. She commented how cute I was, pinched my cheek and gave me a nice kiss.
She sat me down in her desk chair while she did my makeup. Where Catherine was very delicate and gentle during this process, Rebecca had a much more deliberate and efficient technique. It didn't take much time at all for her to lay the foundation, apply the eye shadow, liner, and mascara, put on the lip gloss, and even add a touch of blush to my cheeks. She brought over a mirror and showed me the cute, doll-like teenage girl that she had turned me into (or maybe it was inside me all along). I couldn't deny that my big lips and long eyelashes lent themselves to a feminine appearance. It was crazy to think that I was more attractive as the opposite gender than as my native one. That seemed counter intuitive to me; men aren't supposed to make convincing girls. What did that say about me? Rebecca took her phone and snapped a couple pics before I even had time to feel uneasy about it. She then had me do some poses for her just like Catherine had. I guess photographing the results of a makeover is important to girls, I kind of get it. When she was satisfied, she put her phone away and without warning, she lightly shoved me up against her bedroom wall and started kissing me. Delicately at first, but soon she had her tongue in my mouth while she felt up my ass and chest. I melted into her lust and allowed her to do with me what she pleased. It felt so nice to let go and have someone ravish you. Once again I had the thought - is this how girls get to feel all the time? Carefree, safe, and desired? I liked this feeling of being wanted, lusted after. It was good for my self-esteem, but also satisfied something deep inside my subconscious. A need for validation perhaps? Or maybe a latent predisposition to being treated like an object. I didn't care, I just knew I liked it, and I could only get it when dressed as a girl.
We spent the rest of the day hanging out inside mostly, watching TV, cuddling, joking around. We made a frozen pizza for dinner. She spent some time in the evening teaching me how to dance like a girl. Rebecca was such a sexy dancer. She tried to get me to move like her, but I just don't have those hips. I'd forgotten how much I enjoyed just being with this girl, having her company, and I genuinely think she felt the same way about me. At one point after the sun had gone down, she managed to coax me out into her backyard. I was really nervous, but being with her made me a little more confident. It was still a huge rush knowing a nosy neighbor could accidentally see me like this. Even if a total stranger were to see me I would be mortified. I was comfortable dressing up as a girl with Rebecca and Catherine, because they know me well as a boy, and they recognize that I'm just doing something taboo for fun. But if an outsider were to see this side of me, if the rest of the world saw me this way.... that would make it real. Somehow I could convince myself it was all pretend when it was done behind closed doors, but as soon as something is out in the open for anyone to see, people assume its part of the real you. Luckily no such exposure happened (that I know of). She showed me how to take my makeup off before we went to bed. We slept naked and spooned all night.
I woke up Sunday morning with my body still pressed against hers, my crotch against her butt. If it weren't for the chastity I would be grinding against her hard, but I had lost the bet and I was determined to obey her. We started the day by showering together. She helped me re-shave my whole body (there was barely any hair growth since last time, but she said she wanted me perfectly smooth). I loved feeling her stroke my nice hairless legs and back. I can't believe I used to let my body hair grow free. We brushed our teeth and dried off and returned to the bedroom to get dressed. I wondered what kind of outfit she would put me in today. The panties I had brought with me were some of the last ones I had left to choose from. A bright pink stretchy nylon thong. Pretty much my last choice in terms of comfort and coverage, but it did make me feel sexy. Rebecca seemed pleased by it as well.
"My gurlfriend is such a slut!" she teased. "I'm gonna make you look like one of those sexy club girls today hehe". She wasn't k**ding: she selected a very tight, very short black dress with long sleeves, along with some ridiculous fishnet stockings that she herself would never wear. The dress was smooth and comfy but when it would ride up, my bright pink panties would peek out a little bit. Wearing anything like this in public seemed unthinkable to me, and yet Rebecca was right - this is what lots of girls wear when they go clubbing. She stayed on theme when it came to my makeup: bright pink lipstick, tons of dark mascara and eye-shadow. This time in the mirror I truly didn't recognize myself. I wonder if anyone else could recognize me? I looked like a hooker. No other way to describe it. I felt that sexy objectified mental state come over me. It was like I'd painted a target on myself. I could feel deep down that looking this feminine and provocative made me a potential prey for horny men. I imagined walking through a crowded bar looking like this, and it seemed about as scary as swimming with sharks. The thought thrilled me - the danger of someone deciding to treat me as their sex toy. Simultaneously degrading and flattering. Luckily I was safe in my bubble with only my girlfriend around.
Rebecca sat on her living room couch and beckoned me over with her finger "Come get some sugar, you little whore". I stood in front of her and she pulled me by the hips so I was kneeling on the couch straddling her lap. I had seen girls make out with boys in this position in movies - as a matter of fact, Rebecca had made out with me in this position. It was interesting being the one doing the straddling. I felt safe and supported and very comfortable actually. I felt small and cute, like a kitten. Rebecca pulled my dress up to expose my ass. I felt the cool air and her soft hands caressing my cheeks. It tickled a bit and really turned me on. We made out like that for a glorious 45 minutes. I was completely out of my head, just lost in the passion. Two sexy girls fooling around on the couch while home alone. I realized this is just a fantasy for so many guys, and I am lucky enough to get to experience it from with in. Girl on Girl porn had always been my favorite, and now I basically had a way to do it for real. I was on cloud 9.

Chapter 13: Company
Rebecca had to take a break and go to the bathroom so I curled up on the couch to wait for her. She had been gone maybe 30 seconds when I heard the unmistakable sound of a doorknob turning and opening. Someone was coming into the house. Someone other than my girlfriend. And I was sitting in the living room, an insecure teenage boy dressed as a (very attractive) hooker. The word 'fear' doesn't even begin to describe the alarms going off in my brain. I had to hide. My first choice would have been the main floor bathroom, but that was occupied by Rebecca and I knew the door would be locked. Both the stairs to the basement and the upper floor were located near the front door, where the intruder had now entered. I could hear some heavy footsteps, so I knew he was big and I knew he was coming closer. Maybe if I was lucky I could get out of the living room and into the kitchen before he saw me, but then what? that was a dead end. Or perhaps I could wait until he's in the kitchen, then sprint to the front hallway and get upstairs. But what if he came to the living room first? the footsteps were getting closer. I was standing in the middle of the living room paralyzed with anxiety. There was no good course of action to prevent being seen. I was about to be caught in my girlfriends sexy clothes. And I don't even know who was about to see me. Was it a robber? or a cop? Was it her brother? her Dad? oh fuck if her dad sees me like this its over for me. He'd never let a sissy date his daughter.
A deep male voice called out "Rebecca? Hey Rebecca are you home?". Okay, it wasn't her dad, and it didn't sound like a robber either. A family friend maybe? I straightened out my dress as best as I could and went into survival mode: I looked like a girl - I looked nothing like my boy self. I was literally in disguise. So whoever walked through that doorway, I was going to pretend to really be a girl. They would think they were talking to a female friend of Rebecca's, and they would never know that they'd just walked in on a boy in panties. I started taking deep breaths and told myself 'You can do this. Just relax and be natural'. I hadn't quite finished composing myself when my unexpected guest got to the living room entrance. I froze when I saw him. Total deer in the headlights. Standing in front of me was a a very tall, dark, athletic looking man, maybe in his late 20s or early 30s. he wore cargo pants and a blue T-shirt. Didn't have much style, but he had strong handsome features and nice big biceps. My guess was that he didn't put much effort in his appearance. He looked right at me and raised his eyebrows. Remember that feeling I talked about of being vulnerable and objectified as a sexy girl? Well I had never truly experienced it until I was under the predatory gaze of a real flesh-and-blood manly man. The contrast between his appearance and mine amplified every bit of girlishness I had previously felt. Being a girl around other girls, I just felt like their equal, but being a girl in front of this big man made me feel more like a meal. Or a pet. Or a toy. A doll. Powerless and pretty, only existing for his desires. The silent staring contest only actually lasted a fraction of a second, before he addressed me.
"Oh I'm sorry, I'm looking for Rebecca. You must be a friend of hers?" I nodded, wide-eyed and mouth agape. "Cool, nice to meet you. Terribly sorry if I freaked you out by storming in here. I just came by to drop something off for Rebecca and the door was unlocked so I let myself in. Figured I'd say hi. What was your name? I'm Dave". Shit, what was my name? I didn't have a girl name. Fuck. In nervous high pitched voice, I stammered out "I'm.... Stef... Stephanie! but everyone calls me Stef." I can't tell you why I picked that name; its just the first thing that came out of my mouth. Thank god I said a normal name and not some gibberish. "Nice to meet you Stef." The polite brute walked over and put his hand out to shake mine. I meekly offered my soft little hand and he gave it a good firm shake, eliminating any doubt that he was more confident and physically imposing than me.
This awkward surreal exchange was interrupted by Rebecca returning from the bathroom, and finding the two of us standing in the living room. "Dave!?" she exclaimed incredulously, before running up and giving him a big long hug. She asked what he was doing here, and he gave her the same vague story he gave me. "I just met your very cute friend Stef" he says, gesturing to me. "I think I gave her a bit of a scare haha." Rebecca shot me a a sneaky look with narrowed eyes, as if to say 'clever girl'. Thankfully, she went along with my little facade and explained to Dave that 'Stef' is one of her friends that she met through Catherine earlier this year. Wait did Dave call me cute? I blushed deeply and felt some butterflies awaken in my stomach. An involuntary giggle slipped out of my lips. I couldn't believe he thought I was a real girl! Or maybe he saw right through my act and was just going along with it to be nice? I couldn't know for sure, and that made me feel uneasy. I just wanted him to go away so I wouldn't feel like such a delicate little damsel in front of my girlfriend. But much to my shock and horror, Rebecca asked if he wanted to stay and hang out with us for a while. Dave chuckled "Well there's nothing I enjoy more than hanging out with a couple of pretty girls". My girlfriend shot me a playful wink as if to say 'Let's see how well you handle this'. I was fuming inside but I didn't want to rock the boat and blow my cover.
Rebecca suggested we play some video games, which I was all for, but they decided on some NFL bullshit that I don't know how to play at all. So we sat in the living room taking turns playing against each other, winner-goes-on. Of course they are both super into football, and I suck so I ended up sitting out just watching for the bulk of the time. They decided to have a couple beers, and I don't drink so that's one more thing they're doing without me. I'm basically just sitting around dressed as a slutty girl while my girlfriend drinks and plays video games with some older guy right in front of me. And to make matters worse, they were sitting on the floor, and I couldn't think of a way to do that without my dress sliding up and revealing my pink thong and chastity bulge. So I pulled up the ottoman and sat with my legs tightly crossed. I tried to keep my hand on Rebecca's back or shoulder so she wouldn't forget I was there, but Dave kept making her laugh and stealing all her attention. I wasn't having a great time. Occasionally Dave would take a break from flirting with my girlfriend to make small talk with me, tossing out casual questions about me and my life. I would give simple answers in the high pitched voice that came naturally to me ever since he showed up. Once or twice I cracked a joke and made him laugh. I didn't like him, yet I found myself wanting his approval. At one point he asked what my boyfriend's name was. Rebecca held back laughter while she watched me to see what I would say. I sheepishly replied that I don't have a boyfriend. Dave's response was "Really? A hot girl like you being single? That's crazy". I blushed out of both embarrassment and bashfulness. He called me a hot girl! Right in front of my girlfriend, who found this all hilarious apparently. When I showed up to this house for the weekend, I thought it would be me (a guy) hanging out with my girlfriend. It had somehow turned into two girls hanging out and flirting with some older guy. Was she even still my girlfriend? It sure didn't feel like it at the moment.
After an hour that felt like a year, Dave stood up and said he had to go take care of some business. I breathed an ill-concealed sigh of relief. He gave Rebecca a big hug, and offered me another hand shake. I politely offered him my hand (which was dwarfed by his) but instead of shaking it, he brought it up to his lips and gave it a kiss, like some old-timey gentlemen. A shudder went down my spine. I did not enjoy the uninvited intimacy from this jerk. As soon as the door closed behind him Rebecca turned to me and burst out laughing, letting out all of the amusement she had been concealing in front of Dave. I couldn't help but giggle too, though I was a bit frustrated with her.
"Wow. He seriously had the hots for you haha." she declared in disbelief. I pointed out that he seemed to have the hots for her too, to which she replied "No way, Dave's just a good friend. But awweee is my little gurlfriend jealous of an older man? You worried he's gonna steal me from you?" She was poking fun, but frankly that's exactly how I was feeling. She pulled me close and gave me a big kiss and told me not to worry about silly Dave. Any physical affection from her was always enough to quell my anxieties about my status with her. She could just about get away with anything as long as she hugged and kissed me after and told me she loved me. I was a sucker for that stuff. She continued, "Anyway, Dave has tons of other girls he can fuck any time he wants. He has no reason at all to try and get with me. You don't need to worry about him." She held my face in her hands affectionately. I was surprised Dave had 'tons of girls' - he seemed like a boring slob to me. I asked Rebecca about it and she casually replied "It's just cause he's such an Alpha Male." I had heard that term before in science class when learning about pack a****ls. I asked her what she meant by it. "Oh you know. He's just always in control. People just sort of do whatever he wants because he seems like a leader. Girls go crazy for that shit, so he's rolling in pussy without even trying haha".
We spent the rest of the night dancing, watching TV, eating snacks, and making out. I was finally enjoying myself again, but I couldn't stop thinking about all this 'alpha male' business. It sounded like Dave was the opposite of me (especially now as I sit in my pink thong and fishnet stockings). So if he's what girls want, does that mean I'm the opposite of what they want? It made sense, I had always struggled with girls. I was 18 and I'd only fucked one girl - once. Most of my male classmates had fucked many girls, many times. I was way below average when it came to girls wanting to have sex with me. And yet I had many good female friends, most of which were actually very attractive. And sometimes they even say I'm cute. So girls do like me, at least to an extent. But there was something going on here...
While we were cuddling on her bed I asked her softly "Do you wish I was more of an 'alpha male' like Dave? its okay if you do..." She put her arms around me and gave me a nice warm squeeze "Don't be silly baby. I'd much rather have a nice sweet cute boyfriend who does whatever I want. You see honey, girls might like fucking guys like Dave, but they don't want to date him long term. Because guys like that are never loyal - they need to fuck everything that moves. So they don't make good long term partners. And that's why boys like you are better in the long run; I know you'll never cheat on me. Come to think of it, you can't even if you wanted to" She gave my plastic-encased crotch a little tap and laughed. I felt my fragile dignity leave my body. "Speaking of which, you've been a very good girl for me all weekend, so I think I'll let you cum before you go. How does that sound baby?" I agreed with significant fervor.

Chapter 14: Cum like a Girl
She instructed me to remove my panties and get down on all fours in the middle of her bed. I cast off my panties and got in position before you could say 'cum'. I didn't realize it at the time, but I think the degradation of being seen as a girl by a more macho guy had added something extra to the arousal that had been building inside me. As an insecure boy it had been humiliating, but from a purely sexual perspective it was just so kinky. Boys aren't supposed to dress up as slutty girls and flirt with older men. That was very naughty of me, and feeling naughty was a huge turn-on. I was so excited for whatever Rebecca was about to do to me. She produced some rope from a box under her bed. I thought it was odd that she just had rope lying around but I was too horny to question anything. She pulled my wrists together and tied them to her headboard in front of me. then she tied a loop around each of my ankles, and secured them to the left and right corner posts, so my legs were pulled apart exposing my dangling genitals between my legs. My ass was also right out in the open since my short dress had ridden up. I wasn't going anywhere, and if someone wanted to do anything to my ass, I wouldn't be able to do a damn thing about it. I once again sank into the helpless feeling of being a defenseless sexual object. I imagined what it would be like for a girl to find herself in this position with a man in the room. The fear that he is almost definitely going to fuck you, and you don't have a say in the matter. I shivered and squirmed in anticipation. She put the rubber ballgag in my mouth and fastened it tight. Now I couldn't get away or even ask for mercy. I have zero control. Looking at my perilous predicament, I realized that I am certainly the opposite of a dominant 'alpha male'. Suddenly I found myself thinking about Dave. What if he were to come back over right now? What would he think if he saw me like this? What would he do? Surely he would see my little package and know that I'm really a boy, not a girl. But with my ass all smooth and inviting, and my dick locked up and concealed, would he even care about the difference? Rebecca said he'd fuck anything that moves. That could very well include 'cute little girly boys in bondage'. I felt a panic response beginning in the back of my mind.
Meanwhile my sexy female captor had stripped down to just her bra and panties. She stood behind me, reached up between my thighs and unlocked my cage, thus freeing my penis. She barely caressed it with the tips of her fingers, and dragged her hand back along my balls and taint and eventually began tickling my exposed ass cheeks. My dick was rock hard already, and I was frustrated that she touching my ass and not my cock. It's not like I can cum from having my ass played with. Maybe she sensed my discontent and read it as ungratefulness, because she ceased the caressing and switched over to spanking. She slapped my ass several times, one cheek and then the other, harder each time. She had spanked me several times in the past. It wasn't a big deal then because I could grab her wrist to stop her - sometimes even spank her back. But now I was restrained and powerless. I couldn't ask her to stop, and I damn-sure couldn't make her stop. "This is for flirting with my friend Dave today. What, you didn't think I noticed the way you were looking at him?" She continued punishing my soft ass with her firm hand. I didn't know what she was talking about, I didn't even like having Dave around. "Making eyes at him, laughing at all his jokes. Are you trying to get him to fuck you? Do you want a real man to fuck your tight little ass?" I shook my head urgently. "Good. You belong to me. You will not get fucked by anyone else unless I say so. Is that clear?" I nodded in passive agreement. She stopped the beating and rubbed my ass gently and even planted a few soft kisses on my cheeks. A wave of warmth and comfort washed over me.
At long last she squirted some moisturizer into her hand and begin massaging my cock from behind, like she was milking a cow or something. It felt sort of cold and clinical because I could not see her or touch her. She was just servicing my body in a detached way. It made me feel like I wasn't a full person - more like a piece of equipment or maybe livestock. Despite this passionless method, I was in heaven. I was still wearing my tight little dress, and the sleazy fishnets. Here I was, bent over and dressed up like a whore; restrained in a doggy position while my captor pleasured me from behind. I certainly didn't feel like a man of any sort. This is not how men feel. This is how girls feel, when a dominant man makes them his sex slave for the night. I was a sex slave now. A sexy feminine sex slave.
Rebecca asked me if I liked being her gurlfriend. I knew the answer she wanted, and frankly it was truly how I felt, so I nodded my head and made a high pitched "mhmmm" noise. "Show me how much you like being my gurlfriend. Cum for me if you want to be kept as my slutty gurlfriend from now on." I was so degraded and dehumanized. I felt ashamed, and that shame was converted directly into sexual excitement.
Without warning, I felt her take her free hand and smear some moisturizer into my ass crack. I squirmed in discomfort at the cold slimy invasion of my most secretive region. I had never been touched there like that before. She wouldn't let me escape her touch. She continued rubbing up and down the full length of crevice, while still stroking and squeezing my penis. At first it grossed me out to have my shy anus touched, but very quickly it started to feel like an extension of my penis and scrotum. Sensitive to pleasure; an erogenous zone as its called. She moved her hands around stimulating the whole region from the tip of my cock to the top of my ass crack, and everywhere in between. This was a new level of sexual pleasure for me. She was activating my body in ways that I'd never known were possible. Without even meaning to, I was rhythmically bucking and grinding against her hands, my body automatically reacting to whatever she decided to do to me. I realized this must be very close to how a girl feels when she gets fucked from behind; her pleasure zones filled and stimulated while her every muscle is commanded by the control of her partner. The relentless burdens of free will and existential angst thoroughly replaced by submission, passivity- and most of all - pleasure and lust.
My kinky puppet-master repeated her humiliating demand "Cum for me if you want to keep being a slutty gurl for me." I didn't have time to consciously consider the implications of that gesture; my body decided for me. The warm sensation of lubricated hands sliding all over my forbidden areas erupted into euphoric muscle spazms and butterflies filling my entire body. She emptied my cock into her open hand. It took several moments for the frantic spurts to subside, and when the dust cleared she had an overflowing handful of warm sticky cum.
I settled down in my restraints and started catching my breath while I waited expectantly for her to untie me. My mind came down from heaven and began to wander. I finally understood feminine sexuality. Women don't like being objectified when they are just trying to go about their lives in public, but behind closed doors, being turned into a sex-toy by a dominant partner is the absolute peak of human joy. This is why they go for meathead jocks and arrogant 'alpha males' - they need to feel dominated in order to fully satisfy their sexual hunger. This is also why being physically good-looking isn't enough to make a guy desirable - he must be dominant and in control. A timid unassertive boy like me could be perfectly handsome and still not be sexually appealing to a girl. And I was not perfectly handsome - I had soft gentle features. Once again I felt insecure about my ability to fulfill my girlfriend's needs. Speaking of her needs, I realized we hadn't had sex in weeks now, and I hadn't been manually getting her off the way that she was milking me. Shit, had I been neglecting her completely? Is that why she keeps doing all this weird humiliating stuff to me? Is this whole feminization thing really a way of getting back at me for not being a good boyfriend? I'm failing to be a man so she's turning me into a pathetic undignified 'sissy'? Oh god. These terrifying revelations began spinning around in my head. I had fallen down a rabbit hole of sexual subjugation. These past few days I had just been starting to think being turned into a girl was a nice thing for me, but maybe it's actually the most disgraceful thing that could possibly happen to a man. After all, that's what I'd been brought up to believe my whole life. It didn't help that whole I was considering all this, she was putting the chastity cage back on my now-dormant genitals.

Chapter 15: End of the weekend
At her usual leisurely pace, she did untie me and remove the ball-gag. I rolled over and let the experience sink in for a moment. I blinked my dark mascara'd eyes and licked my pink painted lips and remembered how ridiculous I must look. I asked her if I could go wash up and change back into my boy clothes, to which she replied "Of course baby. I don't want my girlfriend getting m*****ed on the bus home haha" She tickled me and I slithered away from her and into the bathroom. I washed up, got out of the stupid hooker clothes, looked at myself in the mirror, and wondered where this was all going. I seriously felt like I was going to lose my girlfriend, but I didn't know how or when. Anyway, the last thing I was going to do was voice these concerns and appear even more uncertain and oversensitive. I sauntered back to the bedroom, put my panties back on without being told, and got dressed in my boy clothes. She thanked me for a fun weekend, kissed me goodbye and sent me on my way. I had a lot to think about....