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It is a unique feeling to know you want something different from the norm, especially when it comes to sex. Maybe I was more adventurous than all my male counterparts. Maybe deeply embedded in my DNA, I was bisexual, and just never knew it until I experienced it. Perhaps some felt as I did, but never acted on it. I would be bold enough to suggest that some of the men and women I knew in life never took that chance because of fear of retribution, teasing, or being shamed. All I knew was the doors of wants opened a flash flood of desires after Chuck. I accepted that as much as I loved women, loved being inside a vagina. Loved playing with tits, and loved experiencing sex with every one of them that I could fuck, I was now at the point where I wanted dick. And I wanted dick, just as bad as I wanted pussy. Even though at that moment I had only blown Chuck and had one brief make-out session with Jillian, just holding her dick, I knew I wanted more. And for the time being, my focus was moving forward with Jillian.
Jillian and my conversations grew after our heated car-kissing session. And I think she was just as scared as I was about developing something more. I knew the minute I crossed the line and sucked her dick; I was going to have to determine where my destiny laid. For her, I think the fear revolved around becoming a woman and getting the love she desired. Yet, also knowing she could never be that “regular woman.” She wasn’t going to have kids; she didn’t have a pussy. She would be introduced to family members or parents as the “girl” someone is dating, who has a dick. And I can only imagine the anxiety and apprehension that would come with that.
I never really pushed the issue of asking her about her sex life before me. I knew she had dated a few men, but I didn’t even know if she was taking dick during sex, or giving dick during sex. So, anything further with us was going to be a learn-as-you-go moment. Just like any relationship, you grow and develop how comfortable things can get, or what turns someone on. How you interact, what your partner does, or does not do. So only time would tell for us. More importantly, only time would tell for me on whether or not, I liked having only dick, fucking her, or even her fucking me. But that moment quickly arose and I found out.
Jillian came by my house Saturday night about a week and a half after our golf date. I promised to make her dinner, sit and have some wine, watch a movie, and just enjoy each other’s company. She arrived wearing tight blue jeans, a short-sleeved off-white feminine button-up shirt, little white gym shoes, and white ankle socks. Her hair was up in a ponytail and her make-up was on point. I’m sure we were both nervous about the evening, being it was the first time we were alone behind closed doors. But as the conversation with us increased and the dates we had gone on, the more comfortable we had become around one another. Just like any first night alone with someone in privacy, there’s always that bit of apprehension.
After dinner, Jillian and I sat on my couch watching a movie and we were holding hands and just lightly passing conversations as we watched. I wanted to kiss her again. I wanted to be feeling her up and I wanted to see her dick. I could see the bulge in her pants, not from her being hard, but as she sat next to me, I could see there was a package there, instead of a slim, tight pussy. I may have appeared to be cool as a cucumber, but I was a nervous wreck on the inside.
When that moment arrived, and the tingling inside came as we stared into each other eyes and kissed for the first time tonight, my heart thumped loudly. There was no doubt that if this went beyond our heated exchange in the car last week. Tonight, I was going to be sucking dick, instead of playing with pussy, and as much as I had ensured myself, I was ready for this, I wasn’t sure I was ready.
As we kissed and as our passion grew more, my mind eased a bit, and I just went with the flow. Just like the time before, when I felt the time was right, I slid my hand onto Jillian’s shirt and was feeling up her tits over it. They were firm, ridged, and plump, and still had that hard ballon feeling. But I had to understand and accept that they weren’t real. As time went on, I unbuttoned her shirt, which she eventually slid out of, exposing her skin, except the bra she was wearing.
I pulled Jillian up on top of my lap and we just continued kissing deeper and maslak escort more intently as things progressed. I was feeling up her tits over the bra and rubbing my hands along her back, sides, and neck slowly seducing her. I unhooked her bra and felt it start to fall, Jillian, pulled from our kiss and slid her arms through the loop hoes, tossing it off to the side. I got a good look at her full, plump, affixed-in-place breasts that were more rounded and firmer than any breasts I had seen before.
I slowly kissed my way down her neck and across her chest until my mouth hit one of her nipples. I proceeded to suck on both as I went back and forth from holding one and sucking on one, flipping back and forth to make her feel aroused. When our faces met again, we started kissing deeply, Jillian pulled me slightly forward and pulled my polo shirt up and off of my body. Her hands slowly and softly rubbed my chest and upper torso, as she stared intently at me.
When we returned to kissing, I slowly rubbed my way down past her breast, along her sides, across her stomach, and down into her crotch area. My hand slid up and down over her dick, over her pants and I could feel her body’s reaction to my touch. I will admit it was a wild feeling to know I was rubbing over a dick and not a pussy, and I could feel her hard cock nestled deep inside those jeans, almost begging to be let out. I was rock hard at that moment and I wanted her to suck my dick, as bad as my desire was growing to suck hers.
As I popped her jeans button open, Jillian made a grunting, groaning noise and I froze. Had I gone too far? Too fast? I pulled from our kiss and asked her, “Are you okay with this?”
“Yes,” she replied, as she smiled at me.
“Then why the grunt?” I asked.
“I’m excited,” she replied as she leaned back in to kiss me more.
I unzipped her pants and did my best to slide my hand down into them, but with her sitting on top of me, I couldn’t get the best angle. I could feel her hard dick sticking up in her panties and I was doing my best rubbing over it, as she was getting more aroused because she was moaning and groaning, kind of rocking up and down as my hand slid up and down over her.
Jillian pulled from our kiss with a big huff of excitement and arousal, looked me deeply in my eyes, and started to slide herself off of me and down onto her knees onto the floor.
She looked at me in a longing, loving way for a few seconds and reached for my jeans button. She unbuttoned them, unzipped my zipper, and in a surprise move, grabbed a handful of my pants and underwear at both sides and started pulling my jeans down off of me. I lifted my hips and tried to help her as she wiggled them down my legs. Talk about a moment of embarrassment, as I was now naked on my couch, dick hard, sticking up as she pulled my pant legs from my body, exposing me and leaving me rather vulnerable. I felt very uneasy at that moment. I almost felt as if she was judging my dick size. Was I big enough? Manly enough? Did I look sexy to her? Even more frightening was my mind knowing that even though I was looking at a “lady,” I was about to get a blow jo from “a man.”
Jillian pulled her hair back into her ponytail tighter and then her hands started rubbing my legs, softly opening them, getting her first good look at my naked body. She started kissing my inner thighs, above my knee, bouncing back and forth from one leg to the other as she moved upwards. I spread my legs open and slightly shifted down as her hand reached out and grabbed my stiff dick.
Her hair and her breath came across my dick first and I felt her mouth right at the tip. She slid the tip of my dick just inside her mouth and I gasped ever so lightly, as it slid ii in. As her mouth encompassed all of my shaft, my heart was pounding. I felt her wet warm mouth take it all in and start slowly retreating towards the tip.
I was in complete astonishment. Just seeing her head slowly start bobbing up and down. She was deliberately slow at first, just taking it all in and getting accustomed to me. In my mind, I was screaming for her to go faster, to suck it tighter, to make me want it more. As she continued the slurping, sucking sounds started to fill the room. I could feel her tongue swirling around my dick as slid in and out of her mouth. Her pace quickened and on occasion, she would use her hand in combination making it feel like she was squeezing the skin off of escort gebze my dick. I had my hands resting on top of her head and I knew she could tell she was getting me more aroused and even closer to orgasm than I was seconds before.
As the minutes went on, I was getting closer and closer to cumming, but I didn’t want to cum yet. I surely didn’t want to cum and not be horny enough to return the favor. The time had come and I needed to suck her dick, just as she was doing mine.
I pulled Jillian up from blowing me and pulled her face to mine kissing her softly as her hand still held my dick.
“I want yours,” I spoke through our kiss.
Jillian pulled away from me, leaned back on her knees, and started to stand up. She reached for her jeans at the hips and slowly slid them down off of her legs, bending as she pulled her feet from them. As she stood back up, I could see the tip of her dick poking out of the top of her silky pink panties. There was no denying, those panties were full of balls and dick. Jillian slid her panties down, bending ever so slightly at the waist to get them completely off. As she rose back up, she stood naked in front of me. I could tell she felt just as embarrassed and uneasy as I had moments ago. I looked her over from top to bottom, seeing her beautiful face, and her clean neckline. Her plump, rounded tits, rested perky and set in place. Her stomach with just a bit of chubbiness around the mid-section and her hard dick sticking straight out towards me, with a long full set of balls hanging below them. Her smooth shaved legs, led to her bony knees and calves, which were strong and meaty.
I stared at her shaved dick, just in awe that I was seeing it for the first time. It was 6 and a half inches or so long, about the same as mine, but she was more plump or fatter than mine and I was so excited, yet so nervous about it.
I edged forward on the couch and shifted my head down. I reached out as she moved closer and wrapped my hand around her dick. The head on her dick was perfect, rounded, smooth, and plump as it pointed out from the end of my palm. I leaned further down and without letting fears and apprehension stand in my way, slid her dick into my mouth. I took it all the way in and slid it back out.
I felt how hard she was. How the “bone” inside her cock was firm and ridged, how the skin slid across my tongue. I rocked back and forth just letting it slide in and out of my mouth, feeling what it was like again to suck a dick.
I was at a bad angle and was much too tall sitting on the couch to pleasure her the way I wanted. I pulled her dick from my mouth and guided her a step back as I slid off of the couch and onto my knees. Now I truly came face to face with her erect dick and I slid it right back into my mouth and started sucking on it as if I was sucking a candy treat.
I could hear Jilian moaning lightly; huffing as I was sucking it. I bobbed back and forth, head shifting from side to side, occasionally taking it out of my mouth and licking up and down her shaft, only to take every bit of her back into my mouth, deep into my throat.
I was still rock hard and felt like I wanted to cum as I was sucking her off. I could only imagine what my neighbors would have thought if they could have veered through my window, seeing what appeared to be a woman standing over me while I was bobbing back and forth sucking her dick.
I was enjoying the moment because it wasn’t a lost bet or some impromptu moment this time. I had met her, became friends, and now we were becoming lovers with someone I had been looking for in the aspect of having a dick.
I wasn’t sure if I was sucking it correctly or not. If I was pleasuring her the way she needed, but either way I was on my knees, my mouth full of saliva, as a hard dick slid in and out of it. I was doing it! I was sucking dick again! I was nervous, aroused, overwhelmed, overly anxious, overly jittery, and unsure of how and when this was going to end. But I was doing it. I WAS SUCKING DICK!
Jillian and I went back and forth taking turns sucking each other’s dick. We went back and forth from the couch; to the floor, to kneeling, just taking in the moments of giving each other head. I think every time one of us got close to cumming we’d switch positions to make this moment last longer. Each time I got to put her dick in my mouth, my passion for it grew stronger. I wanted to escort merter suck it. I wanted to feel it in my mouth and the hornier I got and the closer I got to cumming, the more I needed that dick in my mouth. I couldn’t have wanted it more. It was like a drug. The more I tasted it, the more I got it, the more I had the chance, the more I needed it. I wanted to know every aspect of it. The taste of it. The deep-throating feeling I was getting from it. How plump, round, hard, and sexy it looked. How I made her moan as I was slurping and gulping it down. How my head and neck started working in combination with the right flow, becoming more in tune with sucking dick. I was becoming a cock sucker and that night; I was loving every minute of it.
I came first, blasting every drop of my cum deep into her mouth. She swallowed every bit of it and let my dick rest in her mouth a few moments longer as I dripped out the last little bits. I then rolled her onto the couch from her kneeling position and I went back down on her.
I knew eventually she was going to cum. That’s when the biggest fear and panic ran through my head that night. Should I swallow it? Should I let it slide from my mouth as I did when Chuck came? Should I just let her cum on herself? Should I just jack her off when she moans “I’m going to cum,” and let her explode freely?
I wanted to swallow it. I wanted to know what that felt like. I had swallowed my own in practice, but that was way different from someone else cumming in my mouth. This was the first dick I had in years and I wasn’t sure I was ready.
When Jillian started moaning, she was going to cum, I truly felt her cock get harder and fuller in my mouth. I just kept bobbing up and down getting ready, but feeling cowardly that her cum, was about to come. Just as I heard that grunt start, I pulled her dick from my mouth and started jacking her dick, keeping my chin pinned along the top of her dick, pressing my face down as she squirted her cum out.
I looked up at her – as if I had swallowed some – and just kept jerking her off as she continued to spew her load. When she finally finished cumming, I slid her dick back into my mouth just getting a little taste of the last little bit that was trickling out. The rest of it was on my hand, my cheek, and her balls, but I didn’t say anything. I just went with the moment as it had been “accomplished’, but yet she wouldn’t know she didn’t cum in my mouth.
When the moment had come and passed for both of us, we ended up cuddling on the couch, lying naked pressed up against one another. Just holding our bodies close, kissing occasionally, and whispering conversations. We held one another for a while basking in the warmth of our first sexual encounter, in the darkness of the room, with only the flickering TV providing light.
Jillian stayed with me for a while, but as the night grew later, she decided it was time for her to go. I watched as she got dressed as I lay on the couch. To see her slide her panties on and tuck her dick back into them was something I was enthralled by. She followed that up by putting her bra on, tucking her tits inside the cups. Her pants then shirt followed until she was fully dressed and adjusted correctly. It was incredibly interesting to see. I’d seen women do it hundreds of times but never watched someone with a dick do it. It was wild.
I got up, dressed, and walked her to the door. We kissed goodbye, sharing pleasantries about how wonderful the night was and she left. I watched her walk out to the street, get in her car, and drive away before I shut my front door.
I laid in bed that night, relieved I had cum and had got the chance to experience dick again. I wasn’t sure it was absolutely where I wanted to be in life. As much as I talk about becoming a cock sucker, at that moment it time, I was still very unsettled when it came to dating someone with a dick and I struggled with the thoughts. It wasn’t the experience that scared me, I enjoyed being with her, sucking on her dick and making her cum. It wasn’t the dick, as weird as it is to say, it was whether or not I could live that lifestyle permanently and come out to everyone that I was dating a shemale. Words that haunted me, and her for a long time.
It turns out that through the course of our 7-month relationship, Jillian had more fears and concerns than I did, which would all be revealed after some very emotional, aggravating conversations. But before I get to the end of her and I. I will tell you about our first anal experiences and the host of blow jobs we had leading up to our eventual separation and my moving forward in life. But that night at least, I went to bed excited that I had given another blow job!
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