Losing My VIrginity

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Losing My VIrginityI had been dressing since I was a p*****n, sneaking into my older sister’s room to “borrow” anything feminine I could find, a pair of panties, a bra, some cute sneakers or even her cheerleader uniform. It was a ritual I would submit to anytime I was home alone for a long enough period of time to transform into my gurlie persona. I changed names often back then, from Tabitha to Kaitie (short for Kaitlyn) to Ashley before settling on Tiffany by the time I was in my late teens. No matter the name, my feminine form was that of a naughty little teenager who was boy crazy, the only problem being, I didn’t know how to meet boys without the risk of being caught. It was the 80’s and the internet was not around so I was forced to resort to vegetables and homemade phallus’s to quench my thirst for penetration. Sure, the self-exploration led to thousands of orgasms but I always longed for more, a personal connection with a boy who would show me what real pleasure was. After years and years of being Tiffany by myself I finally found an outlet and made a connection that would change my life forever. I was in my early 20’s and saw a local paper as I was leaving a bar, you know the ones, listings for local bands and venues, things to do around town, lame stories no one reads and then, there on the back page, I saw the ads. They were for massage services (hookers lol), escorts and 976 numbers. You all remember the 976 numbers, right?I was looking through them and saw one that stood out, it said alternative lifestyles. I was intrigued, and drunk, haha. So, when I got home, I slipped into my room and dialed the number. It was a personal ad service and it was free to place your ad. The categories listed were straight, gay and gender bending. I immediately placed an ad as Tiffany and stated my desire to meet a man who would show me how to be the gurl I’d always dreamed I could be. To my shock, I had about 30 replies by the time I checked it the next day. The only problem was you had to pay to get your responses. I was a poor college student at the time but decided it was worth the $40 or so to get all my messages.I was so excited when I finally got through the signup process and clicked the number to play my incoming messages. OMG, was it disappointing. I had like 10 from the same desperate guy begging me to come fuck him, a few from another guy who wanted me to be his mommy and discipline him, and some random guys just leaving incoherent messages (guessing they were drunk like I was when I left my ad).There were a couple that did sound promising though. One stood out to me, his name was Wyatt and he lived about 15 miles away but said he had a place he could host and that he’d love for me to come over and hang out. He had left his number and sounded like a nice guy but you never really know, right? Well, I called him that evening and, in my best girly voice, not the nearly perfected one I have now mind you, I left him a message from Tiffany stating that I’d love to come over and hang out that night. After a couple hours of no response I’d figured I would be spending another night on my own being Tiffany. At about 10:30pm I got a call from an unknown number. I was super nervous but didn’t want to pick up in my Tiffany voice in case it was a friend calling from a different phone so I let it go to voice mail. It was Wyatt and he said he’d just got my message and wanted me to come over. I called him back right away and told him since it was so late and I hadn’t heard from him I’d need some time to get ready. He agreed and set up our meeting at a Lowe’s parking lot right around the corner from his place.Once we hung up I rushed into action. I jumped in the shower and shaved my legs (I kept them shaved regularly so it wasn’t too big of a job) and pubic area as well as my chest and face as closely as I could. I got out and dried off before setting to getting my makeup on. This was my early days of doing makeup and I’m sure it was horrendous but I plastered on some eye liner and shadow as well as some mascara and blush before doing my lips in a bright red color that stood out garishly. I got dressed in a simple outfit, a white cotton thong and bra under a cute long blue skirt and a white blouse. I clipped the ankle straps to my black platform heels and then put on my shoulder length brown wig. I looked in the mirror and knew I wasn’t passable but I thought I looked pretty cute, I hoped Wyatt would think I looked cute too. I had to navigate my way out of the house without alerting my roommates since they didn’t know about Tiffany. I slipped out of my room and down the hallway trying not to click my heels too loudly on the wood floors. I really should have put my heels on after leaving, something I figured out for the future. I tiptoed down the hall and made it to the front door unnoticed. I was on my way. I jumped in my car and headed for the freeway. I had been out driving while dressed before so that wasn’t a first but the butterflies I had in my stomach were even more pronounced with the anticipation of hooking up with a boy just moments away. I could barely concentrate on the road as I headed down the freeway driving the speed limit like a grandma. I for sure didn’t want to get pulled over, how embarrassing would that be? I finally made it to my offramp and pulled right into the Lowe’s parking lot and called Wyatt as we planned. He said he would be right there and within 10 minutes I saw a tall young man striding towards my car, it was about midnight and I was the only one in the lot. He opened the passenger door and sat down. I could tell he was just as nervous as me. I was shaking and couldn’t even bring myself to say anything. He was a gentleman but his voice trembled as he tried to say hello. His bolu escort nervousness eased mine a bit and I finally said hello and leaned over and kissed him on the cheek. He smiled and directed me towards his place. It was right across the street from the parking lot, a quick right and then a left at the light and we were at a gated entrance to his complex. He had the clicker and opened the gate for us. He had me pull down a long alley and then opened a garage and had me pull in. He was being extra cautious and I couldn’t blame him. He said he wanted to make sure no one saw a guy in a dress going into his condo, I get that he was worried but it wasn’t really a nice thing to say. He immediately apologized when he saw my frown and said I looked very cute and that he didn’t mean to imply anything. I told him it was ok even though I was still a little hurt. We walked into his living room and he offered me a drink. I was so nervous and worried that maybe this stranger would slip something into anything he offered me so I declined. He opened up a Bud Light and sat on the couch across from me. He asked again if I was sure I didn’t want anything and I said no thanks. He asked what I wanted to do and I told him whatever he wanted. It was so awkward.Neither of us seemed ready to make the first move and it made me wonder if he was attracted to me at all. He was tall and handsome and I really wanted to have sex with him but I didn’t know if he wanted me. Now that I’m older and wiser I’m sure he was having those same feelings because he finally asked if I wanted to suck his dick and I practically sprang off the couch onto my knees in front of him and pulled his pants down. I pulled his rock hard dick out of his underwear and was a little surprised by the size of it. Wyatt was probably 6’3” and I figured he’d have a pretty big cock so it was a little shocking to see his penis was probably about 5 inches and not overly thick. It was actually about the same size as mine, maybe a little thicker, which I always thought was extra small. Nonetheless, I set about giving my very first blowjob. I’m sure it wasn’t the greatest but I gave it my best. I licked it all over while I massaged his balls and then shoved it all the way into my mouth. It fit without really going into my throat so I guess it really wasn’t a deep throat but he sure seemed to like it. After about two minutes I felt him start to breath heavier and then he began to shudder and I knew what was happening. The first spurt hit the back of my throat and made me gag. I pulled off of his dick only to be hit in the face with the next two or three shots. I’m sure it wasn’t a pretty picture, me choking and coughing with cum dripping off my chin as he stroked himself off. I was so embarrassed. I figured he’d be looking at me like, ‘Who is this dumb slut?’ But when I looked up he had his eyes closed, head back and was just massaging his cock in his hand. I gained my composure and took his cock out of his hand and began to stroke it while I kissed it and licked up the cum that had dribbled out onto his balls and into his pubes. There was a big puddle on his thigh that I lapped up as well. I looked up at him as I tongued his member and he smiled down at me. My heart was aglow from his acceptance and I knew I’d find myself in the position as soon as possible. I sucked on his dick until it was completely flaccid and drained. Wyatt had to ask me to stop haha. He thanked me as I slid up on the couch next to him. I asked him where the bathroom was so I could go clean up. He told me how to get there and I went to wash off my cum-covered face. As I looked in the mirror I instantly got hard. I saw a slutty looking gurl with jizz all over her nose and lips and it turned me on to know I made a guy cum. I really didn’t think about it till then but I don’t believe I had a hard on at any point while I was sucking his dick. Kinda weird to think but whatever. We had spoke about what we wanted to do on the phone and I had said I wanted to suck his dick and get fucked so I figured we would be kicking off round two as soon as Wyatt was ready. I lubed up my asspussy while I was in the bathroom cleaning up and walked back out as sexily as I could. Wyatt was leaning back on the couch and looked up. I told him I was looking forward to getting him off again. He said he thought that would be fun too but that he didn’t think he could go again that night. Boom, I was crushed. I felt rejected and wanted to leave right away. It got really awkward again as I slid down on the couch. He asked if I was okay and I said I was fine. I said maybe I should just go.I was hoping he’d say something sweet and ask me to stay but he just agreed and said he’d show me out. What a jerk! Here I was, not more than five minutes before, sucking his dick and making him cum all over the place and he was done with me. Now that I understand boys a lot more I get what had happened. He was feeling weird about things and once he nutted he lost all desire to do anything with me, it is something I’ve experienced time and again in the following decades. Men, even when they are with people they are secure being with lose interest after sex. Add in the fact that he was likely questioning his sexuality and it makes a lot of sense. Being that it was my first time being intimate with a guy it really hurt me and made me feel inadequate. I didn’t react very well. He walked me out to the garage and tried to give me a peck on the cheek but I just pulled away and got in the car. I said, “call me later,” but I knew we’d never be hooking up again. I drove home upset and crying and wondering why I had thought it would be a good idea to hook up for the first time with a total stranger. The flood of emotions was overwhelming. I escort bolu got home about 1:30am and looked at my phone. I had other messages on the personal ad line and I thought, ‘screw it,’ and dialed back in. Daniel seemed like a nice enough guy on his voice message and he said to call anytime. I punched in his number and he answered. I told him who I was an he said he’d love to meet but he was married and couldn’t host. I told him I lived with roommates and couldn’t either. I thought that would be it but he suggested he get a cheap room and we meet there. He lived a couple miles away and said he’d call me with the room info if I was really ready to meet him. I told him I was down. True to his word he called with the address and room number about 20 minutes later. I was still dressed and had cleaned up my makeup so I was ready to go quickly. The motel was in a seedy part of town where there were hookers and d**ggies so I was a little worried about that but I was still horny and wanted more dick. I pulled up to the motel about 2:15am and there were a lot of people milling around the place. The room was right at the top of the stairs but I saw people sitting on the bottom steps and others hanging around on the railing of the upstairs walkway. I was super nervous now. What if he wasn’t there, what if these people said something to me, made me, what if I was propositioned. OMG, so many things were going through my mind. I wanted to leave and go home for a moment. Luckily, for me, I was still super turned on and I wanted to get with Daniel bad enough to overcome my fears. I was parked about five spots down from the stairs so it wasn’t too far to walk but I would definitely be passing by some people who were likely to be of highly questionable character. I slipped out the car door and adjusted my skirt, flipped my hair back over my shoulder and grabbed my purse. I took a deep breath and headed for the stairway. As I approached I saw two Mexican guys sitting there smoking, they had brown paper bags and were drinking from them. Their eyes locked on me as I walked up to pass by them and they stared at me the whole time. It actually made me feel pretty sexy the way they leered. I even swayed my hips a bit for them as I made my way up the stairs. One of them even whistled at me and called out, “Come back Mami!” I was sooooo happy. I got to the top of the stairs and the room was right there, straight ahead. I saw the people on the railing looking at me and heard one of them say, “That bitch is about to get fucked,” as he laughed. I just ignored them but I was hoping he was right. Daniel opened the door after I knocked and invited me in. He had told me he was in an unhappy marriage over the phone and that he needed someone to do the things his wife didn’t like to do anymore, namely, suck his dick and take it anally. We seemed like a perfect match. He also told me he was taller than me (I’m 5’10”) and had and athletic build. He was still shorter than me when I took off my 5 inch heels and he had a pretty good-sized beer belly. I am a thicc gurl so I wasn’t mad he was overweight but he did lie about it. Not cool. He also told me he had a fat 7.5 inch cock. Needless to say, I don’t know how he was measuring but it might have been 6 inches at best. Anyway, I was super horny and Daniel was very affectionate right off the bat. He invited me in, complimented me on my outfit and wanted to make out with me. I felt like I was desired and it felt amazing. He lifted my blouse over my head, slipped my skirt to the floor and removed my bra. I was standing there in my thong, waist cincher and stockings as he admired me. He gently pinched my nipples and kissed my neck before moving to my lips. He forcefully pushed his tongue into my mouth and feverishly kissed me until I was gasping for breath. I felt his hard cock grinding against me and I reached down to feel its strength and rigidity. He pushed me down to my knees and placed his hand on the back of my head and guided me to his cock. I started out slowly but Daniel had other ideas. He shoved my head onto his cock and started ramming it down my throat. I tried to resist but he was too strong and kept pushing it deeper until I was gagging and drooling all over the place. He started to call me a bitch and tell me what a slut I was. I have to admit, I was scared but it really did turn me on. He let up a bit and I pulled off his dick. I looked up at him and he just coldly told me to suck his cock. I must have hesitated too long because he grabbed his dick and started to slap my face with it. I tried to grab it with my hand but he smacked my hand away and told me, ‘Use your mouth only bitch!’ As I tried to corral his rod in my mouth Daniel continued to batter my face with it until I finally managed to get it back in-between my lips. I sucked his cock for a few minutes with a lot more deep throating and drooling, I was a mess, before he decided we should move to the bed. He laid me down on the edge and proceeded to fuck my throat some more until my face was covered my my own spit. He laughed at me and said I was a good whore then had me lay on my back as he placed his cock on my sissy pussy. I told him he needed to wear a condom. He said he forgot to grab them when he left home. I told him he couldn’t fuck me, that we needed to be safe. He said he had been married for 23 years and he had never cheated before (yeah right) and that he was clean. He said he was more worried about me. I told him I’d only been with two girls before and that I was a virgin as a gurl. He told me, “see, we’re both safe and clean baby, just lay back and I’ll make you a real girl.”I was young and stupid and horny so I bet you can guess how it went. I let him push his raw dick inside my sissy pussy bolu escort bayan and, for the first time in my life, I was getting fucked. Now I had had a lot of things in my asspussy before, I’d even gotten a dildo by this time so it wasn’t a foreign feeling having something thrusting into me. That doesn’t mean it was anything like fucking yourself. When a man enters you it just feels different. The warmth, the lack of control, the emotion and the vigor with which some men fuck is hard to replicate by yourself with a toy. So when I felt Daniel thrust into me it was a feeling I’d never experienced before. He was gentle at first and he let me adjust to having him inside me. He kissed me and stroked my nipples as he cupped my little boobs. He told me I was a sexy bitch and that I was going to fucked so good I’d be begging for his dick all the time, that I was going to be his slutty side-piece.I kissed him back and told him to make me his gurl. He began to pump his cock in and out slowly at first and I could see it felt good for him by looking as his face. It felt good to me too as I adjusted to his girth. He picked up the pace and started to fuck me harder and deeper and I just held on with my legs as he sat up and pounded away. He grabbed my little dick and stroked it a bit but he was focused on his pleasure and that, strangely enough, made me feel even sexier. He was really getting into in and turned me over into doggy style. As he tried to reenter I could feel he was getting a little softer. He slapped it on my ass and spanked me before he finally shoved it back inside my sissy box. He fucked me for a few more minutes but I could feel he was having trouble staying hard. What a blow to a gurl’s ego. I asked him if he wanted me to suck him again and he pulled out and I turned around and put it back in my mouth. I looked up in his eyes so he could see how badly I wanted to please him. He seemed frustrated and told me that he sometimes had issues. I tried to reassure him that it was ok but he was a little agitated. He said sometimes if he takes little break the sensation comes back so we laid there on the bed and rested a bit. He was playing with my nipples and reached down to play with my sissy pussy. It was still wet from the fucking he had given me. He slipped a couple fingers in and started to roughly finger my hole. I tried to squirm away but he was firm in his grip and continued to stretch and explore me with his fingers. I told him to stop but he just said, ‘you know you like it cunt!” He was now laying across my back, pinning me to the bed with one hand pulling my right leg aside while his hand was doing its thing to my asspussy. I couldn’t move at all and was starting to get worried he might hurt me. I guess my struggles to get away from him turned him on because he moved in behind me and I felt his cock, rock hard again, stabbing at my pussy. He slipped it in and began to pound me hard and deep and fast. I told him to make sure he pulled out before he came, that he could cum on my face or tits or in my mouth but not to cum inside me. He completely disregarded me and held my hips tightly as he thrust as deep as he could before emptying him balls inside my sissy twat. He gripped me so hard I couldn’t pull forward to get his dick out of me in time. I struggled as much as a could but he just held me there as he filled me with his cum. Then he laughed as he finally slipped his cock out and said, “damn slut, I think you might get pregnant, that was a huge load.”And he was right, I felt it leaking out running over my balls and down my leg. I was tired, upset and still so turned on as I slid down on my stomach and rested. I closed my eyes but was jarred by the thud as his still-dripping cock hit my face. “Clean it up bitch,” was all he said. I dutifully cleaned this asshole’s cock with my mouth like a good slut. When I was done he silently walked off to the bathroom and I heard the shower turn on. I lay there contemplating what had just happened. It was infuriating and exhilarating at the same time. I thought about how I had longed to have sex as a woman for so long and how tonight it finally happened, though, not exactly how I had wanted, but still it felt amazing to know I could please a man. Daniel came out, got dressed, packed up his stuff and said he had to get back home. He’d paid for the place for 3 hours so I had some time if I wanted to clean up before I left. I told him I’d love to see him again but he said he was in marriage counseling with his wife and they were trying to make it work but we’d keep in touch. He left and never returned a call from me again. “What a JERK!”With everything that had happened that night I just wanted to get home. I went to the bathroom, fixed my wig and wiped off my face a bit before getting dressed. I put on my heels, grabbed my purse and got ready to make the walk back to my car. I looked out the window and saw there were still plenty of people around the motel. The two Mexican guys were still at the bottom of the stairs and I was worried they might give me some trouble. I knew I had to get going sooner or later so I opened the door only to be startled by the motel janitor who had a plunger in his hand. Apparently he had to do some work in the room next door and was exiting the same time as me. He just smiled and went about his business. I sighed and headed down the stairs. My two friends both started to talk to me as I made my way down towards them. “Damn mamacita, you’re so fine!”“How bout we go back upstairs sexy mami?”I just smiled and walked on by to my car. I have to say, I was tempted but they were drunk and I wasn’t sure they knew I was really a gurl and not a girl. I didn’t want to find out the hard way if they got upset with me. I got in my car and buckled up and headed home. It was a crazy night for sure and nothing went the way I had always dreamed it would but I was well on my way to womanhood and I knew I would enjoy learning how to be Tiffany as she and I matured.

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