Continue Crossdressing Adventures

I want to thank everyone for their comments on my journey into cross-dressing, even those that were negative. It has been a number of years since I submitted my last story. Life gets in the way sometimes.

For those of you that didn't read my last story let me give a little background. I stumbled into cross-dressing for my own self gratification and then as a method for my girlfriend, Sherry and I to party and drink for free. This worked well until I allowed myself to be put in a compromising position and the only way out that I saw was to comply and give the guy I was with a blowjob. That was a first for me and I wasn't looking for a repeat engagement. This is all in my first offering, now to continue.

After Sherry and I left the bar we headed to her house. Once there I ran the gauntlet of getting past her father again and we cuddled together on her bed talking about the night and what had just happened. Sherry grilled me for details of what actually happened with me and Jim. She kept pushing me for the details so eventually I told her how he had guided me into his car without my really thinking, his kissing me and how he was trying to get under my skirt and into my panties.

I suspected that Sherry would get upset but instead she was being more of a sympathetic girlfriend. Thinking about it, it made sense as I am sure that she had been put into similar situations in the past. As we lay in her bed slowly running our hands over each other Sherry continued pressing me for details. She wanted to know how I felt, what did I like, what didn't I like, what exactly did Jim and I do together, would I want to do it again, am I interested in doing more, etc etc.

Eventually, I gave her all the details of my time away from her while in the club and in the backseat of Jim's car. I even confessed to sucking his cock and swallowing his load. I did explain that I didn't have any intention to swallow and was totally unprepared for his ejaculation.

Rather than becoming upset, it was more like Sherry and I were girlfriends gossiping into the night. She told me about the first time that she blew a guy and how it felt to her. The excitement, the feeling of being desired, the power of making someone weak in the knees, the fear that it was a little out of your own control, the unknown.

I wasn't really too sure of what my emotions really were until Sherry confessed how she felt during the first time as well as every time she sucked a cock. I could easily relate to all the emotions that she was telling me about and more.

I was able to identify the underlying excitement below the initial emotion of fear of discovery. The feeling of being so desirable that the guy you are with can't resist. As strange as it seems the feeling of being powerful and in control of a situation when you really aren't was intoxicating.

During all this talk, Sherry had slid her hand under my skirt and was rubbing my ass through my silver silk panties. Our talk and her ministrations were having the desired effect on my manhood. She slipped her hand inside my panties and began stroking my cock.

Sherry lifted my skirt next and proceeded to get face to face with my little "big" man. She placed a kiss on the head of my cock before slipping the head into her hot mouth. She slowly snaked down the length of my shaft until hitting bottom before working her way back up to the sensitive head of my cock. Once there, she popped it out of her mouth and asked, "Truthfully, did you enjoy it? How about his cum, did you like the way it tasted?" I didn't immediately answer and tried to get her to resume sucking me. Instead, she just blew a cool stream of air across the head of my cock and told me to answer her questions.

I told her that after the initial shock of the position I had put myself in, I did come to enjoy it on some level. With that she gave my cock a big, wet kiss and asked, "Well how about the rest?" She was making it clear that she wasn't going to resume the attention that I craved until I answered her completely.

I told her the truth, "I didn't really like it. It wasn't the worst thing that I'd ever tasted but it also wasn't anything that I desired to experience again." She laughed and said, "It is an acquired taste but it does tend to grow on you. With that she resumed her ministration on my rock hard dick.

All too soon she stopped sucking and asked me another series of questions. She kept teasing my cock with little licks, nips and kisses until I answered this round of questions of which the last one was, "Would you do it again for me so I could watch?"

"I'm not sure" was my last answer.

Sherry resumed my blow job but again stopped too soon. I was sooo close to exploding that it hurt. She was keeping me right on the edge. Once again she cooed, "Please, just one time for me. I won't ask any more questions." She was running her hands up and down my nylon covered legs from my knees to my ass.

I couldn't take it any longer and said, "Yes I will, please finish sucking me." Sherry wasted no time dropping her head and taking my entire length and started bobbing her head while sucking like a Hoover vacuum cleaner. In very short order, I shot spurt after spurt of hot jizz into her mouth and throat. Sherry, ever the trooper, took it all. When she was certain that I had shot my last squirt she popped off my dick and looked me directly in the eyes. She leaned in and kissed me as if she would never kiss anyone again. She plunged her cum covered tongue into my mouth. She had her hands wound into my hair and even though I was trying to pull back she wouldn't let go of me.

Only when she was done and satisfied that I had had a good taste of my own cum did she pull back. It was then that she said, "See how easy it is to get what you want?" "I'll teach you how to keep control of the situation with minimum effort."

I asked her if she was really going to hold me to my agreement? Sherry told me that she had to think about it but thought it was really sexy and made her hot.

We continued hitting the clubs and having fun for the next couple of months. Sherry, good to her word, taught me how to control situations when dealing with the guys. Every time we visited a club or bar we were hotter and hotter, dancing with each other, licking each other's necks, kissing deeply, grabbing each other's asses, you get the scene. This would drive the guys insane. They would come by our table or booth and hit on us and buy us cocktails. Occasionally we would dance with a hot guy. I found that I enjoyed being lead onto the dance floor and held by big strong guys. I really liked it when a song of the right tempo came on and I could grind my tight ass against his crotch and feel his cock swell.

It was after a night out where I spent more time than usual on the dance floor with guys than with Sherry where upon returning to her room we engaged in some heavy petting which lead to my head between her legs eating away at her hot box. Sherry, not to be out done had flipped my skirt over my waist and pulled my throbbing cock out of my panties and was alternating between deep throating me and sucking on my balls.

It didn't take very long and we both exploded in each other's mouths. When I climbed out from between her legs and stood up, Sherry did the same. She wrapped her arms around my neck and pulled my head to hers, kissing me with passion. She then stuck her tongue into my mouth bringing with it a dose of my own cum. She kept her lips glued against mine, swirling my cum around in my mouth until I eventually swallowed it. Then she pulled away and said, "Not so bad is it? You expect me to swallow you stuff now we can share!"

We separated and went to her bathroom to freshen up before going to bed. I pulled off my skirt, washed up and slid into bed in a pair of string bikini underwear, stuffed bra and t-shirt. Sherry was dressed similarly but didn't need to pad her bra.

Sherry started kissing me, rubbing her legs up and down mine and finally grabbed me by the ass. She was telling me how hot it made her to see me swallow my on cum. She went on saying that the only thing hotter would be if it was someone else's semen and coming straight from the fountain so to speak. With that she grabbed my hand and put it right on her panty covered pussy.

She was so hot that her panties, which she had just put back on in the bathroom, were already soaked. Moments later I was working my fingers in and out of her moist hole and she was stroking my rock hard cock. Almost as quickly, both our panties were off and she had mounted me and impaled herself on my hard dick. Sherry was bouncing up and down, riding me as good as any cowgirl could ride a bronco, one hand playing with her own tits while the other was squeezing mine.

I was in heaven. After a few minutes, I rolled us both over and started pounding my gal as hard as I could. She was biting her pillow to keep her moans down while grabbing my ass and pulling me into her with both hands. Sherry slipped a finger into the crack of my ass and started playing with my ass hole which only made me fuck her harder. As I was approaching orgasm, she penetrated my ass with one finger up to her first knuckle. I shot my load so hard into her that I thought it might go right through her. To her credit she reached a magnificent shuddering, pillow biting orgasm as well. Sherry came so hard that she scratched my back with one hand while the other clinched so tight it felt like it was trying to rip my ass open.

As we both started to calm down Sherry said to me, " You are one horny slut aren't you? You liked my finger up your butt didn't you? Can you imagine what a real cock feels like?"

I said, "That was unbelievable, I've never cum so hard in my life!" "Not sure if I liked it but it was intense."

We laid cuddling and talking in bed. It was almost like two girlfriends sharing experiences. I was asking Sherry what did it feel like when I fucked her, how different was it with different guys, did she like longer or thicker, is there a perfect size?

Sherry answered as if I was her girlfriend, not her boyfriend. She told me that there were multiple feelings involved depending upon the situation but that the physical sensations were always very similar. All cocks felt good, thick cocks made her feel full while long ones could feel like they were up in her stomach. She explained that some guys, "like me", just knew the when, where and how buttons to push that set a girl off but that the real difference was in the emotional connection. She went on and said that when a cock first enters her it was so intense, like merging bodies, then as it slides deeper into it almost becomes an out of body experience as there is an object moving inside you that is not you but it is hitting all kinds of pleasure points. You know where you want it to go but it has a mind of its own.

My gal continued, it feels so good but at the same time so foreign inside, that is until the pleasure overrides all other feelings and then you are along for the ride until you hit your climax. She said, obviously guys fuck differently, how they stroke into you, how hard they fuck you, what motions they make and of course the size and shape of their cocks. Sherry went on and told me that for her the emotional connection led to the most intense gratification but that if all else was equal her preference was to a slightly bigger (longer & wider) than average cock with a bigger than average head.

I only have an above average cock in length but only average in girth and head size. She described the feeling of a big cock head penetrating her as crazy good but again she said that for her the connection was a multiplier to her feelings.

We had talked for about 20 minutes and were both thirsty so I jumped up, slipped on a pair of panties and a pair of Sherry's short-shorts and was on my way to the kitchen to grab us a cold drink out of the fridge.

As I opened the refrigerator all I could think of was how Sherry described the feeling of a cock in her and what her finger felt like in my ass. I wanted to ask her how anal sex differed from vaginal sex to her. While thinking of everything I wanted to ask her, I was busy searching the shelves for a Gatorade, soda or bottle water. I was bent at the waist looking on the lower shelves when a hand came gently down on the small of my back and a crotch pressed lightly up against my bum.

I jumped and bumped my head on a shelf. Shit it was Sherry's dad, he said "Stay just like you are, don't move too fast, let me look at your head." With that he kept his hand on my bare lower back, thank god I still had on my stuffed bra under my t-shirt, and leaned further into me as he used his other hand to check my scalp and head. In leaning into me he pushed his crotch harder into my upturned ass. I could feel his cock against my butt and it was growing.

He declared, "Well you seem to be in good shape. Have you found what you are looking for or can I find it for you?" I swear as he asked the last question he moved his growing cock a little harder against my barely covered ass cheeks.

I must have lurched a little bit making my ass to wiggle against his growing manhood. His hands slid down to my waist where he held onto me for that fraction of a second too long before saying, "Let me know if you need anything, I'll make sure you get it."

With that he walked away leaving me scared shitless but excited as all get out. There was no mistaking that my girlfriend's father had just made a pass at me as a girl.

I grabbed a Gatorade and a couple stalks of celery, don't ask why as I have no idea, and hurried back to Sherry's room. I came through the door and she took one look at what I brought back and started laughing.

Sherry asked, "What are you thinking of doing with that celery?" Up to that point I hadn't even realized that I had grabbed celery. I shrugged my shoulders and started telling her what had just happened in the kitchen.

Sherry was laughing uncontrollably and I don't think she saw the seriousness of the situation from my eyes. I blurted out "What if he had found out that I'm actually a guy, he would have killed me?" Sherry really didn't believe that her father had made a pass at me, but did admit that looking the way I did in her short shorts along with the fresh fucked look on my face, she couldn't have blamed him if he did.

With that she started calling me a horny slut trying to seduce her dad, saying, you'll do anything to make a cock stiff. This was all in good nature and in fun until it turned serious when Sherry said, "I think I want to see you fulfill your promise and suck some dick in front of me, slut! The time to honor our agreement is coming."

I asked her if she was really going to hold me to that promise, to which she affirmed that she was and soon. I was both excited, and nervous, well more than nervous.

With that I dropped the shorts I was wearing on the floor and we snuggled together in her bed under the covers. I was breathing hard as well as sporting a hard on from what she had just told me she was going to make me do. Sherry noticed my excited state and said, "I see someone really likes that idea." I told her that really wasn't it (not totally true) but that it was her sexy body next to mine that put me at attention along with our sexy talk earlier in the evening.

Sherry said, "So you liked hearing what it felt like to be penetrated did you?" I had to be honest and told her that the way she described it was downright sexy. I then asked her what were the differences when we engaged in anal sex over the normal vaginal sex?

Her answer was, "As you are the only one to ever have my ass I don't have a lot of experience to compare you with but it is similar while being different. There is a slutty or taboo side that makes it different. She explained the need for some lube at least initially which made the experience more pleasurable. The pressure as you start to enter me is sort of the same but since my butt is more constricted than my pussy it is more intense but the feelings when the head of your cock enters me is fairly similar. Obviously, as you go deeper there are different nerve endings being affected, but once I've adjusted to you being in my ass and you are fucking me in and out it is similar to when you are fucking my pussy, but different.

My dick was cobalt steel blue by this time listening to my sexy girl describe me butt fucking her. This did not go unnoticed by her. My goodness she said, looks like someone is even more excited, I'll have to help you out or we won't get any sleep.

With that she slipped below the covers, pulled my bikini panties down and went to work pleasing me with her talented mouth. As I laid on my side with her between my legs, she took my cock all the way into her throat even putting her hands on my ass cheeks and pulling me into her face. She kept me lodged in her throat for a few seconds then pulled her hot mouth completely off my throbbing cock. Then she slipped the head past her lips and started a slow decent down my shaft. Sherry picked up the pace slobbering all of my rigid cock. She popped my rock hard dick out of her mouth and asked me if I wanted her tight ass right now? Of course I did! She grabbed some lube from her nightstand and handed it to me telling me to get her lubed and loosened up.

I wasted no time attacking her sweet ass, first with my mouth and tongue and then with my lubricated fingers working one then two fingers in and out of her tight ring. I put a liberal amount of lube on my rod and started pushing through her sphincter ring. Unbeknownst to me, while I was thoroughly enjoying myself in her dark tunnel she had taken the bottle of lube and applied a liberal amount to her fingers. As I was approaching climax she slipped a finger deep into my rectum causing me to erupt in her bowels. As I was squirting inside her, Sherry was fucking my ass with her finger causing my orgasm to continue. Sherry continued stroking her finger in and out of my semi-virginal ass. She was curling her finger while it was deep inside me and the resulting feelings were keeping my cock erect. After a couple of minutes I felt her trying to add a second finger into my ass. At this point I tensed up and asked her to quit. My little minx complied but not without first telling me that I was a little slut and she knew I enjoyed her taking my ass. She also told me that this was just the beginning as turnabout was fair play.

We both feel asleep shortly thereafter. When we awoke, Sherry hadn't forgotten about my promise to let her watch me suck a cock. She proceeded to tell me that next weekend was going to be the big event. Truthfully, I didn't want to do it, but this was my HOT girlfriend and I also didn't want to piss her off over a promise that I made to her.

Shall I continue the journey or am I boring you too much?