Five days, five long days of pure lust, five days of squealing, five days of begging, five days of throbbing, five days of kissing, five days of teasingly hellish pleasure, five days and lots of cum ingested, five days and not a single drop of paint used, five days out of fourteen years of life, is all it took to show me how much I loved being Dru.
The lies to my parents had become quite elaborate, `No, no Dad, really I'm ok, I'm just walking funny because of all the ladder work we did today', or `Mike fed me a huge lunch that's why I'm not hungry for dinner Mom', which I guess wasn't a huge lie. Nonetheless, neither Mike nor I could come up with a lie big enough to explain needing to continue working for another week at his house, so we took a break after five days of wonderful sex. Mike was a lot like Steve, which shouldn't have surprised me, as he had no qualms about giving as good as he got. Mike gave me the most wonderful blowjobs, they were slow and teasing, and when I would finally cum, I could have sworn I was going to blow his head off. I relaxed for most of the weekend, letting my beautifully sore holes recoup, knowing full well that as soon as my parents were gone on Monday, I would be back at Mike's house begging for more.
Monday morning came, and I was woken to the sound of my Mom shutting the door, on her way to work. I sat up and rubbed my belly, as a huge yawn escaped, my hard 5" dick, the only thing excited to be up this early. I finished showering and stepped out into the bathroom, the water dripping off my naked flesh, I barely recognized the boy in the mirror without my make-up and breasts. For fun I threw on my Moms silk robe, as I walked back to my room. I was eating breakfast when Mike called, and asked if we could talk. The sound of his voice, made me think, this wasn't going to be good. I quickly threw on a sweatshirt and ran out the door. When I got to Mike's house he seemed to be waiting for me, and opened the door.
"Hi Drew, come in, come in, have seat real quick," he said as he pointed to the couch.
"Is everything alright Mike," I asked worried by the serious look on his face.
"I hope everything is alright sport, I've just been doing a lot of thinking, and I'd like to know how you feel about what happened last week; does it bother you? Are you ok with it?"
Thinking about his question for a second, "Well it was a little weird the first day, but yeah I liked it, I liked it a lot, and it's not like you hurt me or anything, did did you not like it?" I asked concerned I had done something wrong.
"Oh God no Drew, I loved it very much, no, no it's not that, I've just been thinking that it was, well, wrong of me to do that. I mean I know you say you liked it, and I'm glad, but I shouldn't have pressured you into, you should have chosen to do it, and you're so young compared to me, and well with everything going on with you and my kids, I shouldn't have gotten involved with you, but that's just how I'm feeling, it has nothing to do with anything you've done, or didn't do, ok?"
"Oh, ok Mike, but you know I would never say anything to anyone right, you know I wouldn't do that.
"I know sport, I'm not worried about that, I'm more worried about you; what we did was fun, but perhaps a little to adult for you, and definitely too much for you right now, with you trying to figure out who you are and all. I think you know what I'm talking about Drew, right?
"Yeah, I get it I guess, but does that mean you and I can't fool around anymore, I don't want it to end."
"Well for right now I think we should stop, but I'll admit it Drew, I am attracted to you, and I don't think my will power will let me stay away from you completely, but I'll let you make the call from now on, when you think the timing is right."
After agreeing to what Mike had said we continued to sit there and talk about how it came to be with me wearing girls clothes and how much I was starting to love it, but that I wasn't ready for people to find out just yet, especially my parents, who were pretty opened minded, but would probably have a hard time understanding this. He then asked how I was able to keep it from them, with all the outfits and wigs and stuff, and I told him about my secret box in my closet, but that he was right, it was getting more difficult as I acquired more stuff. Mike discussed his dislike for the way I was hiding my clothes and came up with an idea that I thought was brilliant; he would tell Dave that he had found our tape, and scold him for leaving it out, but that he also confronted me about it while Dave was at his Moms, and after talking to me, Mike would tell Dave that he was hesitantly ok with me dressing in women's clothes around the house, as long as we all kept it a secret. He would then tell Becca, pretending she didn't already know, but since we both knew she did, we were pretty certain she would go for it, although we also knew she would give him mock disgust at the whole idea. All I had to do was get Dave to let me keep my clothes at their house, and then tell Steve about what happened, so that everyone knew. I was so excited about the whole prospect; it was all I could think about for the next four days until Christmas.
Dave got back from his time at his Mom's, and as we returned to school he filled me in on all the boring details. We also discussed the conversation he had with his dad, about the tape, to which he profusely apologized for leaving out, as we discussed my pretend conversation I had with Mike, and how he said he would be ok with me wearing my women's outfits around their house. Dave felt really bad about the tape, and I am sure a little embarrassed about what his father saw him doing, but he also was excited that I would be able to walk around the house freely in my outfits. And long story short Becca, found me at school that day and let me know she thought it was cool too.
After new years everything kinda went back to normal, except instead of going home to change and jerk off, I now would run over to Dave's house, usually with Dave, and change into one of my outfits and do my hair and make-up. All of my stuff was now folded or hanging in a cupboard in the garage that Mike had cleaned out just for me. With football over, it gave me and Dave plenty of time to fool around each afternoon, before Mike came home, and boy did we ever. I would usually suck Dave off right away, and then after he came we would take a quick break and then he would fuck me, followed by him jacking me off while fingering my pussy, if I hadn't cum while he was fucking me. During each afternoon session, Dave was becoming a little more vocal about his desire for me to finger and rim his beautiful ass, before I sucked on his wonderful tool. Becca, usually went over to one of her friends houses after school, but on the occasions she was home, I picked her brain on all sorts of things from clothes and make-up tips, to hair styles and boys in the Teen Vogue magazine, which I initially started reading for clothing up-dates, as it was hard to get girls gossip on cool fashion, when I wasn't a girl, but I also started noticing all the teen boy photos, and all I could think about is what I wanted to do to them, and Becca usually agreed.
It was the second week in January when Becca found Dave and I in the living room watching TV. I was wearing a tight white t-shirt, and some Daisy Duke jean shorts, a white cotton bra, with the falsies Mike got me, and a pair of white thong panties. My make-up was done and I had my pigtail wig on, the one Becca got me, as I sat on the couch bare foot letting my toe nails dry. Dave had been sitting on the couch right next to me rubbing his hand on my thigh, giving me one hell of a chubby, when he quickly moved to the other side of the couch, as Becca came walking up the stairs from her room, which put her right in the living room.
"Do you guys have a second", she asked looking at us and then the bulge in my crotch, as she smiled.
"Sure, what is it Becca," Dave said, as she sat down on the living room table in front of us.
"Well next week is Winter Formal at Washington High, and Brian and I are going"
Washington High being the cross town high school, and Brian being Becca's latest boyfriend, who just transferred to this town and that school.
"And well we would like to get a limo, and kind of make it a party, instead of just us, but the cost is to much for just us, and all of my friends don't want to go, and Brian doesn't have any close friends yet, Soooo, I was thinking you might want to go."
"You know I just broke up with Amy, so who would I go with," Dave said looking confused.
Both Dave and I were looking at Becca for an answer, as she looked at me and said,
"Well I thought you could go with Dru, seeing as no one there would know you, and well," and now she was looking deep into my eyes, "You're getting really good at the make-up and hair, and I don't think anyone could tell you're not a girl."
"Thanks," I said no longer embarrassed of how I looked as a girl. Looking at Dave, "I guess I would be up for it, if Dave is," I said with a wrinkled face, wondering what his take on it would be.
"Hell yeah, sounds like fun, how much is the limo, does Brian know about Dru, where are we going to eat?"
I had to laugh, I was so happy that Dave had no reservations about being in public with me, and the way Dave could take something and just run with it without a second thought, was something I always envied. You could tell even Becca was shocked at how fast Dave moved with the idea,
"Oh, a, Great! Yeah the limo will be about $50 each, and Brain has no idea, and really doesn't need to, and well we really haven't thought about dinner, but yeah cool, I'm glad you guys are on-board."
Becca left the room with a huge smile on her face, as I'm sure she had figured she would have to do a lot more convincing than she did, hell even I was shocked at how fast both Dave and I agreed to this. Before she left she said we would talk about perhaps going dress shopping and that she thought we should get pedicures and manicures before the dance, I simply smiled and said ok. When the whole idea of what I just agreed to sank in, it scared the shit out of me. I had been in public once with Becca, but it was quick and deliberate, this would be much more. I think Dave could see the concern on my face as I sat there looking into space, wondering if I could do this. Dave slid over and put his hand back on my thigh and started to rub,
"It will be fun, you'll see, plus, Becca and I won't let you get hurt, I promise."
Dave may have been just a dumb jock, but his heart was probably the biggest muscle he had, and when he said that, with the loving look he gave me, I couldn't help but cry.
"Are you ok Dru, you don't have to go, I didn't mean to make you mad," Dave said scared he said the wrong thing.
"I'm not mad, I'm happy, you and your family have been so nice to me, of course I want to go, and especially with you, I'm just nervous."
If Mike wasn't expected home any second now I would have jumped Dave's bones right there, and really shown him how happy I was with his comment, but as it was, I leaned in and gave Dave the best kiss I could.
"Wow, thanks for the kiss, but don't go getting all mushy on me, it's bad enough you're my best friend, almost like a second brother, and well, you're also a girl friend with benefits too, so I don't need you becoming like another sister to me, that would be gross, he said laughing, and then smacking my thigh as if the girl clothing meant nothing, and I was once again his best friend Drew.
That Saturday Becca and I went to the mall for the second time as Dru, this time looking for Winter Formal Dresses. I was lucky as there was no way I could afford a nice dress and obviously I couldn't go to my parents and ask for the money, so I was really lost as to how to make this work, when Mike stepped in and offered to buy both dresses, and anything else we needed. Becca seemed really shocked by her father's generosity, but went with it, I on the other hand knew I would have to pay Mike back, and was excited to do so. Becca and I looked at dresses all day, and we finally picked the two we liked the best. Becca looked beautiful in a sky blue ball gown with an A line pickup skirt, crinkled lame', strapless sequin/bead empire bodice, and pleated midriff. She looked like a beautiful snow princess. Her dress really accented her beautiful eyes and shoulders, and although you couldn't see them, as the dress went to the floor, she also bought a matching pair of blue strappy sandals. I on the other hand went with the formal black color, as I already had the heels to go with it, and I really didn't want to spend too much of Mike's money, as I knew I wanted to look at new wigs as well. My dress was a Vera Wang knock-off, and had what was called a sweetheart neckline, which was strapless, as it wrapped just under my arms and over my chest. There were three pleats over each of my breasts which traveled down to a well defined waist, where the pattern went horizontal in a 4" wide belt if you will, that wrapped around my waist, and from there it flowed into a long pleated skirt. The dress was my first black dress, and it was beautiful, but the fact that it fit me almost perfectly was also a huge selling feature, as having someone take my measurements to tailor the dress was not an option. The final item for the day was a new wig, to which I bought a brunette colored wig, where the hair was straight, and went just past my shoulders.
The day of the dance had approached quickly and all that was left was my nail appointment with Becca. This scared me more than the dance it-self, as there would be someone no more than two feet away doing my nails. I grabbed the tightest long sleeve black shirt I could fined, to highlight my chest, and perhaps erase any doubt of my femininity, and then a pair of capri jeans and a burgundy scarf to throw around my neck. Because I was so self-conscious of the situation I put on the black jock Mike had given me to make sure my little dick was held down as tight as I could get it. I threw on my new wig, make-up, and flip flops, and I was out the door. The outing with Becca was wonderful. We had so much fun; Becca chose a nice blue nail color for both her hands and feet, which we were sure, would go well with her dress. I went with the more traditional French manicure and pedicure. We were laughing and joking throughout the whole experience, and not once did I feel like people were looking at me or judging me. By the time we got home it was about time to get changed for the evening, and ready for our big date.
Becca jumped into the shower first, as I went to the garage and got my black strapless bra, make-up kit and heels, I already had my dress, wig, and the latest purchase I made, a black mesh, floral print, thong, garter belt and stocking set. As I was closing the cupboard, Mike walked up behind me.
"God you're going to look beautiful tonight, I've seen the dress you bought, Wow, I wish I could be Dave," he said taking my hand. "He is a lucky boy, and I have to admit I'm a little jealous."
Looking up at him with a sultry little smile, "I'm sorry Mike, I'll have to make it up to you," I said, looking at his pouty sad face.
Now with a smile on his face, "Is there anyway you can start right now, I mean Dave is with Brian getting the limo, and Becca is in the shower, come on Drew please," Mike said as his hand went to my shoulder, and rubbed it.
I had changed out of my jeans and t-shirt and was just wearing a pair of red shiny mesh boy shorts, white sleeveless undershirt and white socks. Even my wig was off, as I was planning to get into the shower soon, and just needed something to run around the house in. The only thing on from my earlier outfit was my make-up.
"I don't know Mike; I don't think I have time," I said trying to tease him as best I could.
Excitement ringing in his voice, "We can be quick babe, I promise, but ..... I also said that I would let you pick the right time, so if you're not comfortable than I understand"
"Well, you have been really nice to me and it was you're idea to stop, so I might have a few minutes, IF you promise to be quick, no teasing and nothing leather ok?" winking as I said it.
Looking like a kid who was just told he could get anything he wanted in a candy store, "As you wish babe", smiling as he leaned in and kissed me.
Mike pushed me up against his work bench as I dropped the items I was holding. Mike's right hand slid up my thigh as it slid under the smooth fabric of my shorts. His hand stopped on my cheek as our tongues battled. I knew this was not the right time for this, but it felt so good to be with Mike again, and as he dropped to his knees kissing my throbbing boy meat through my shorts, my concern about the clock and how much time I had was forgotten about. Lifting the bottom of my undershirt up he gently placed kisses on and around my belly button, as his hands lowered my shorts, pulling them down and off my legs as I stepped out of them. Mike slowly kissed and sucked on my hairless nut sack, as moaned and bit my lip. Mike worked his way up my hard cock and took it all the way into his mouth,
"Miiiikkkkkeee, ooooooo, shitshitshitshit." My toes were curling in my socks trying to grip the cold concrete floor.
Mike spun me around and started working on my hole, as his hands massaged my bubble butt. At just 5'-4", I was too short to be completely bent over by Mike's work bench, but that bench was the only thing holding me up as Mike worked me over with his tongue. Just as Mike tongue had loosened my ring Mike stood up, with the sound of his jeans and belt hitting the floor. I had a sudden shiver as I felt the warmth from Mike's cock touching my skin. I heard him spit and then I felt the head of his cock push between the valley of my cheeks, looking for its happy place. Touching my lips, his head slowly entered me.
"Oh God Mike, rrrrrrrr, huh huh huh huh huh, you're soo big, ooohhhhh mannnnn,"
I pushed back to feel Mike's bush and boxers. He was still wearing his underwear and it was kind of a turn on. Mike put his hands on top of mine as he drove his steel cock into me. Mike's sheer body size and strength was lifting me off the ground with each thrust.
"Mike mike mike mike, oh oh huh huh uuuugggghhhh, fuck."
"Oh fuck yeah, that's it baby, take it, take it, rrrrrrrr, God you're so tight."
Mike moved his hands from mine and put one hand on my bald pubic area and grabbed my stiff prick with his other hand. His thrusting increased as he drove my dick into his hand, effectively jacking me off.
"Cum baby, cum for me, mmmmmm," Mike said in my ear.
"Yes Mike, shiiiiiiiiit, yes yes, please ohhhh God, uuuuhhhh, huh huh huh,"
I could feel my balls drawing up in what was certain to be a huge cum. My cock lurched as the first shot of cum flew out and hit the shelf below, followed by four more shots, as my pussy gripped Mike's cock. That was all it took for Mike to launch his load up my love tunnel, flooding me with his hot seed. Mike and I stood there for a second to catch our breaths as Mike's cock slowly slipped from my butt.
"Thank you babe; damn your beautiful," Mike said as he kissed my neck.
"Even like this Mike, I'm not dressed," I thought it was only Dru that turned Mike on.
"Babe it doesn't matter what you wear, you have been and always will be beautiful to me, no matter what you wear, or don't wear."
Mike handed me my shorts, which I slipped on, as his cum slowly leaked out of my ass. Mike kissed me before he let me go and I thanked him and rushed to Becca's room walking like I was in heels, as I was squeezing my cheeks together trying to keep Mike's cum from making a huge mess in my shorts. Just as I got to the bedroom Becca opened the door to the bathroom.
"Sorry I took so long, but there should be plenty of hot water," she said looking at me.
Becca was covered in only a towel, which would have been hot to look at, on any other day, but with Mike's cum screaming to come out, I scurried past her and into the bathroom to take my shower, as I said thanks. Replaying the scene from the garage in my head, as I sat on the toilet letting most of Mike's cum go, and how Mike's dick had felt so good, and the added excitement of possibly being caught, had my heart racing. Although, it was a wonderful distraction, I knew I needed to focus on getting ready for my date with Dave. Even though I had shaved recently, tonight was special and I wanted to take no chances, so I shaved once more chest to toe. Becca and I got dressed as if we had been the best of girlfriends, we were giggling and laughing, and I am sure the wine coolers we had didn't hurt the mood either. I knew my panties and garter belt were a little racy, so I wasn't sure if Becca wanted to go that far with our little girl party, in terms of sharing, but when she came out of the bathroom, after having done her make-up, in only a lacy powder blue bra and matching thong panties, I was glad I had shot a load already, or I would have been pitching a tent in my towel. I was also glad we were so open with each other, because I really needed her help with the stockings. Once dressed, I thought we looked pretty hot. Becca had used a very light foundation and eye shadow, to make her beautiful blue eyes pop with her dress. Her long dark hair spun into a stylish bun, laced with pearls to match the one's on her ears and around her neck. I was in my black formal dress, with my new wig, the shoulder length brunette colored one, which was wavy, and covered some of my neck. My shoulders and arms were bare, which I was a little concerned about as they were little more muscled then your average high school teen girl, but Becca said it gave me a fit look, and helped offset my slightly pudgy belly, not fat just not washboard like Becca's. Becca said my arms and shoulders also worked well with my wonderful bubble butt. My dress stopped about mid shin, and you could see my black stockings and heels. With a little help from Becca my make-up was looking better than ever as my hazel eyes were made to look even bigger with the help of Becca's eyelash curler, and a little mascara. Of course I went with a darker shade of red lipstick, to accent my lips, but not make them stand out. I had a pair of clip on fake diamond ear rings, and I borrowed Becca's real single diamond necklace which hung just above the valley of my chest. All in all we were two little bombshells.
Brian and Dave were waiting for us in the living room, with the limo outside. Both Brian and Dave looked stunning in there shirts and ties. Brian, who was clearly of Asian descent, was about 5'-10", with a good swimmers frame, short dark hair, dark brown eyes, and looked hot in his black slacks, white shirt, and light blue tie. Dave, standing just a little shorter than Brian, looked just as good, with his dark wavy hair, sparkling blue eyes, black slacks, dark red shirt and black and red tie. After the whole exchanging of corsages, and photos, which was a little awkward, as Mike was the one taking the photos, and it seemed like everyone was a little on guard, and tense. Once in the limo the date was off and everyone seemed to relax, especially since Mike had put a bottle of champagne in the limo for us. Brian seemed really nice, and it was a lot of fun sitting so close to Dave as his arm held me tight. We had fun making up our story of how we met and started dating, and our past as the dinner conversation was light hearted and joyful. Not once did Brian, or anyone else for that matter, make me feel uncomfortable, and on the contrary, all of the comments on how beautiful Becca and I looked, from the boys, Mike, the Limo driver, and now our waiter, made me forget the little secret I was hiding between my legs.
We arrived at the dance, and after taking another set of photos, we found four chairs around a table, and just observed the dance floor, as we were all a little nervous, with none of us really knowing anyone here. Brian asked Becca to the dance floor and of course Dave and I followed. After one quick dance and one slow dance, I realized the shoes had to go. Once the shoes were off, we had a blast, and although I prided myself on my dancing ability, the slow dances with Dave, being so close to me, and his hand on my butt, were amazing. At one point I needed to use the restroom, and after grabbing my shoes I ran off to take care of business and get back to the dance. In my haste, I made two big mistakes; one I went on my own, which is not in the fashion of teen girls at dances, and two, I ran into the boy's room, without a second thought. With it being toward the end of the dance, no one was really by the restrooms to catch my mistake, and even after going and washing my hands it wasn't until I was walking out that my mistakes were made clear to me. As I opened the bathroom door I turned and walked right into the chest of a boy heading in.
"I'm sorry," I quickly said looking up at a tall boy.
"It's ok, looks like you mis.....read the sign's", he said with a confused and puzzled look on his face.
I turned and noticed my mistake, as I realized I had just come out of the boy's room.
"Drew......Drew is that you?"
Shocked I spun back around and looked at the stranger who just called me by name. I don't know why I didn't recognize him at first, but now it was quite clear, it was Thomas, from my school, the boy who I had just a little over two months ago given a lap dance too at the infamous Halloween party.
"I think you have me confused with someone else," I said looking down hoping he would buy my story. "Sorry I ran into you," I said as I walked by trying to leave the scene.
Not ten feet away from where Tom was still standing, Dave came out of nowhere, and with my head still down I didn't see him as he said with a rather loud voice,
"Dru, there you are, I was wondering where you had snuck off to, we're all ready to leave"
Mortified that Dave had announced my name so loud, I turned to see Tom smiling and nodding his head as he stepped into the boy's room.
"Yeah Dave lets go," I said, hoping to forget the last ten minutes.
The limo ride home was a good distraction from what had happened at the bathroom, as I simply shrugged it off and figured Tom had no proof it was me and no one would believe him anyway, as we laughed and talked about the fun we had. Brian and Becca wanted to use the limo a little longer, and kinda hinted they wanted to be alone, which was fine with Dave and I, as we wanted some alone time as well. The limo dropped us off at Dave's house, and we made it up to his room without any issues, as it looked like Mike was gone. Once inside, Dave shut the door and locked it,
"You were wonderful tonight," he said as he gave me a light peck on the lips.
"Really, you weren't embarrassed or scared to be seen with me," I said looking in his eyes.
"Of course not Dru, you're really are gorgeous, I mean there were a lot of boys looking at you tonight, and I am lucky to be the one going home with you," he said taking my hands and leaning in for a deeper kiss.
Kicking my heels off again, I let Dave lead me to the bed, never once breaking our kiss. Dave gently lowered me into the bed and began kissing my neck and ear with a slow passion I had not seen in Dave before. Dave had me stand up, as he had no idea how to get the dress off, and as I removed it he sat there on the bed looking me over.
"Damn Dru, you're better than any fantasy I could have ever dreamt." "I mean it Dru, your hot, SHIT your hot," he said as he placed his hands on my hips and pulled me, so that I was standing right between his legs, his hands running up and down my stocking covered legs.
When his hands would get to the straps from my stockings to my garter belt I could feel his fingers run under them on my bare legs to just over my panties. Dave leaned in and began kissing my belly and then my belly button.
"You taste wonderful Dru," he said as his hands dragged across my ass and up my back and then around to the front of my bra.
"I don't think we need these anymore," he said as un-did the clasp of my bra, and removed it and my falsies.
"Are you sure Dave, its ok if you want me to leave them on?"
"No Dru, I want you, not some fake rubber tits, but you do wear them well," Dave said just before kissing one of my nipples.
"Ooooooohhhhiiissssss, yeah that feels gooood, oh jeeezzzze.
My boy clit was pulsing hard in the black mesh thong. Before this got to one sided, I pushed Dave back and started unbuttoning his shirt, as he removed his tie, and revealed his amazing chest, which I had become a connoisseur of these last few weeks. Dropping to my knees, I un-did his belt and pants and pulled them to the floor, where I removed everything except his underwear, which was a pair of black briefs.
"Your body is amazing Dave, any girl would be lucky to be with you."
I started kissing up his legs as I removed his last article of clothing. His six and half inches of hard boy meat slapping his body as his underwear released its prize. My lips tickling the hairs on his legs, making him squirm on his bed. Dave sat on his elbows, looking down at me as I approached his dick, my tongue dragging up the underside, and then circling the tip. I had become quite proficient at giving blowjobs, and from the last few weeks with Dave, I knew his first load was always a quick one, and I also knew he really love it when I would rim him. I took his dick in all the way and gave him a couple quick and sloppy bobs, before leaving his dick and heading south.
"Oh God, Dru yes you know what I like, yes Oh man mmmmmm," Dave moaned as my tongue started circling his wrinkled lips.
My saliva dripping all over his boy hole as it loosened and my tongue began to go deeper,
"Pleaaaaassssee Dru, finger me, pleeeaaasee."
The shy little guy I was, loved having my ego stroked among other things, by large guys begging for more. I did what Dave asked and stuck my lubed middle finger gently into Dave's pussy, as I once again took his cock into my mouth.
"Oh shit, yeah oh yeah yeah," Dave whimpered, as he pushed back on my plunging finger.
A few minutes later, and Dave was begging again,
"Please Dru more, please add more, ohhhhh, aaaahhhh, mmmmm."
Wow this was the first time Dave had ever asked for another finger, and his excitement in the moment was making me hornier than ever as my own pole was starting to drip. Removing my middle finger for a second, to a disappointed moan from Dave, I lubed my first finger and started to insert both fingers together.
"Ohhh, yeeaahhhhhh, that's it, oh huh huh huh, yes."
I could feel Dave's hole squeeze down on my fingers as it fought, what I was sure the farthest it had ever been stretched. My new wig cascaded down both sides of my face as I resumed my sucking of his cock, I'm sure adding to the sensation as the hair danced all over his thighs and groin. Dave's thrashing and moaning were getting stronger and I knew he was close to exploding in my wanting mouth. Dave's pussy lips gripped my fingers, his hands clenched the sheets, his back arched and his hips drove his dick into my throat, where he unloaded his hot seed. Swallowing as fast as I could, the first shot hit the back of my throat, and slid down to my belly, where the rest of his load were soon to follow. I pulled back so that I could control when I swallowed as I savored his load, and my cheeks pooled with his baby makers.
In the past few weeks the routine had been the same to the beginning of this evening. I would suck Dave off, we would stop to let him recoup, and then we would start again, where he would fuck me, and I would either cum while he was screwing me silly, or Dave would jack me off after he was done. The situation was fine by me, and I assumed fine by Dave, as neither of us suggested switching it up.
I knew my feelings for Dave were changing; I knew to me he was becoming more than just my best friend, or even a friend with benefits, I was starting to crush on him, and I wanted to take it slow, as this was my first crush and I didn't want to scare him off. So I let Dave determine what we did in the bedroom, as just being close to him, made me feel good, but tonight something was about to change. Dave sat up and looked me in the eyes, as I started to stand, thinking we were going to take a break for a second,
"Come here Dru," he said as he stood up himself.
This was different, but like I said I let Dave lead when we were together. As I approached, Dave took my hands and pulled me into another deep kiss, as one hand went to the center of my back and his other hand to the small of my back. Dave had never kissed me right after I'd given him head; to say I was caught off guard was an understatement. His kiss was deep, as we French kissed with passion. Dave spun us around and laid me down on the bed as he bent over, placing his hands near my shoulders on the bed and began kissing my chest. Dave worked his way slowly to my nipples and now it was my turn to squirm.
"Hhhhuuuusssss, Daaaavvvvve, mmmmm," I moaned.
Dave slowly moved down my smooth chest and belly getting to my thin meshed garter belt. Dave slowly hooked his fingers in the garter belt and panties and pulled them and my stocking down slowly, as his fingers never broke their touch on my smooth legs. I had no idea where Dave was going with this, but I had learned my lesson with his older brother, and there was no need for me to ask, as what Dave was doing seemed pretty GREAT to me. Dave moved to his knees and his head leaned in above my shaved pubic area.
"I love that you're so smooth, so sexy," he said as his kisses were just inches from my dripping dick.
Dave looked at me with a mix of concern and excitement in his eyes, as he grabbed my dick,
"I I've never done this, let me know if I'm doing it wrong, ok."
Dave didn't need to tell me he's never done this before, I knew that, but I also knew this was where I should have said something to reassure him, but all I could do was smile and nod my head. Dave started by licking the head of my cock, his tongue darting around the crown more like an investigation, than an attempt to please me. His lips joined the action as he started bobbing on just the tip. Slowing down but keeping my dick pressed to his lips Dave looked up at me as I sat on my elbows, watching the boy of my dreams sucking his first dick, my dick, he spread his lips wider and took my pole deeper into his mouth, slowly letting it slide in. Dave was either better at this than I was on my first go around, or I was just too horny and excited to care about his skill, but it seemed as though he knew how to cover his teeth, and not once did he choke while my cock got closer and closer to disappearing completely in his wonderful mouth.
"Ohhhh Dave, it's wonderful, ohshit ohshit, yes yes mmmmmmm."
Dave's lips made contact to the bare skin at the base of my dick, as the only sign of his rookie skills became evident, by the excessive saliva flowing all over me, as his lips pushed the warm wetness into my skin. With the past adventures I had been having with Mike, I had become much better at controlling my ejaculations, so I knew I wouldn't cum too quick, but damn if this wasn't HOT! It was probably only 5 to 8 minutes after Dave had started that I could tell my will power was running thin, and my pending orgasm was fast approaching uncontrollable.
I whispered, "Dave, Dave, Shit I'm gunna cum soon, you need to sto, stop huh huh, Oh man."
Which to my dismay Dave removed my cock from his mouth, but kept jacking me off as his tongue would dart out and swipe at my little cum hole.
"Yeah Dru, cum, cum hard, mmmm," Dave said as my first shot hit his face just below his right eye, and then the next one hit near his nose, as he directed my shooting cock toward his open mouth for the final few blasts, as my thick boy jiz painted his face and tongue.
"MMMM, that's not bad," Dave said giving my cock a couple final swipes, and swallowing what was in his mouth.
"Wow Dave you were amazing, oh man, I can't believe you did that."
"Thanks, Dru, I I just wanted to try some knew things tonight," and while biting his lip, "I guess I'm kinda a mess now," he said running a finger through the wet cum on his face.
Sitting up, and looking at the beautiful boy in front of me, I took his hands this time and pulled him on top of me, "I can take care of that," I said with a smile.
Dave leaned in as I wrapped my legs around him and began licking my cum from his face. Dave and I were kissing deep, sharing what was left of my cum, when I felt his hard cock tickle the skin of my bubble butt. Breaking the kiss I looked into Dave's face,
"Fuck me Dave," was all I whispered before going back to his plump lips.
Dave took one of his hands, as he directed the tip of his cock to my pussy, and gently pushed. His head slipped in and slowly spread open my love tunnel, in what was becoming a common feeling for me.
"Oh God Dave, yes ooohhh, it feels soooo goood," as Dave kissed my ear and neck.
Dave pumped me hard, and although he had cum once already, it was clear he was really excited, as his thrusts were short compact and fast. At one point Dave looked me in the eyes,
Dave's cum rocketed into me as he pumped his cock a few more times grinding his thick curly bush into my cheeks.
"I'm sorry Dru, I couldn't stop myself," Dave said as his cock slipped from my ass.
"It's ok babe, you were wonderful, and you have nothing to be sorry about."
I got out of bed and walked naked to my overnight bag and grabbed my gym shorts from earlier and slipped them on. I went to the bathroom at the end of the hall and cleaned myself of any left over cum, removed my make-up and wig, ran some water through my hair, giving it a short spiked look, and returned to Dave's room. Dave was already in bed, as he pulled the covers back, and I approached the bed as it was a little after 2 in the morning, and we were both tired.
"Do you want to sleep naked," Dave asked looking at my shorts.
"Sure if you're ok with it," I said.
Surprised by Dave's request, as this seemed out of Dave's comfort zone, with me clearly out of my femboy outfit. I shucked the shorts and jumped into bed where Dave spooned with me as we fell asleep, his soft cock nestled into my butt, as he kissed my neck, and whispered in my ear thanks for the evening.
It had only been a few hours or so since we had first closed our eyes, that I was awoken to Dave's hand running up and down my hard pole. Somehow in that short time we had completely rolled over and swapped positions, as I was now the outside spooner. Dave's hand stopped stroking my shaft when he heard me moan, and slowly pushed his butt toward my aching hard on. Although tired and slightly drowsy from being asleep just seconds ago, Dave had my full attention as my cock slowly slid between his athletic cheeks,
"Oh God Dave, huh, are you sure," I panted, as I felt tip of my cock touch his virgin boy hole.
"Yyeeaaahhh Drew, I couldn't sleep, I need to know what it feels like, just go slow,"
Dave swallowed hard as he too felt my cock touch his hole. I couldn't believe this was happening; was Dave really giving me permission to pop his cherry. I gave my hard dick a gentle push forward, as Dave pushed a little back and my head opened him a little with out fully penetrating him.
"Oh GOOODD, Dru, huh huh, is it going to hurt?"
"Yeah Dave, its gunna hurt a little, huh huh , but it will feel real good too. If you're sure you want me to do this you need to take a deep breath and push out with your hole."
Not wanting to scare Dave, but making sure he knew what he was asking for, as I really cared for him. I also knew, that like me, the first time you let someone stick their dick in your ass, the meaning behind it creates a lot more fear, than the actual anticipation of the pain you might experience. Fully awake now I stretched to reach Dave's ear as I whispered,
"I love you Dave, I won't hurt you," as I nibble on his ear and pushed a little harder.
Dave took a deep breath and pushed out with his hole and back with his butt, as the head of my cock pierced his ring.
"Oh shit, oh shit, oh shit, rrrrrr, uuuuggghhh," Dave groaned as I stopped with just the first inch of my five inches in his pussy.
Holy shit he was tight, the only thing I had to compare this to was when I slept with Becca, and while her pussy felt so good, it didn't compare to Dave's hole and its grip and heat around my dick.
"Ohhh, mmm, are you ok, huh huh, do you want me to stop."
"NO. nooo, mmm, just go, ahhh, huh, slow, it stings a little," Dave whimpered.
I knew what he was feeling, and remembering from my past experiences, I knew I could help take his mind off the pain. I began kissing his shoulder blades and the center of his back, as I reached over and started lightly brushing the tips of my fingers over his balls. The warm kisses and gentle tickling, was working as I felt his ring relax a little and my cock slid further in. I had gotten about half way in, and wanted to pull back, but remembering how shocking it was to have Steve pull his dick back the first time, I felt I should warn Dave before I did it.
"I'm going to pull back a little babe, ok, it's going to feel a little weird at first, but you'll get used to it.
"Ok ok, mmmm, ohhhh," Dave said as I moved my hand from his balls and started stroking his cock.
I pulled back a bit, not much but enough to move some of the lube around, as I prepared to push back in, Dave beat me to the punch and pushed back with his beautiful toosh, sinking my cock almost all the way in.
"Oh fuck Drew, shit mmmmmm, damn, huh , ok ok ok, wait wait ok ok ok, fuck me fuck me," he pleaded in a gritty whisper.
I sure as hell didn't need to be asked twice, as I moved my hand from his cock to his hip and started a slow pumping motion.
"Oh Dave, oh man, it feels soo goood, oh jeeze you're so tight."
For the first time I got to feel what Steve, Dave, and Mike felt, as my dick took Dave's cherry. Dave moved his top leg on top of mine, which let my dick slip a little further in, and then he started jerking himself off. The sensation of my smooth groin smashing into Dave's smooth ass, was adding to the unbelievable feeling, as my moaning and thrusting increased.
"Dave, dave, huh, oh man, can I, huh mmm, can I cum in you, ohhhh shit, yes."
"Yeah yeah do it do it, shit I'm gunna cum tooooo, OH FUCK!"
Dave roared as his cock shot its third load of spooge in the last six hours, as I felt for the first time the feeling of a gasping love tunnel, as his pussy squeezed and released my cock in a wonderful milking.
"Here it cums Dave, OOOOhhhhh, Fuck Fuck fuuuuUUUUUCCKKKK," and with that I let my cum fly into my first ever boy pussy.
"Oh shit Drew I can feel it, oh man it feels good, oh God oh God , yes."
Our breathing came back to normal as my chubby flaccid little dick pulled and fell from Dave's hole, to simultaneous moans from both of us. Dave rolled to his stomach as I got an even better shot of his beautiful butt, not as plump as mine, but tight, athletic, smooth and gorgeous. Looking at Dave, with a smile on my face,
"Was it what you thought it would be, was it, you know, good," I asked, nervous he didn't like it or I hurt him.
"It was everything and more than I thought it would be." "I can still feel your cum in me," "I love it, I ...... I love you too Drew."
I had forgotten I had told Dave I loved him in the throws of passion,
"Really Dave, I love you so much, I think I have for a long time."
Dave smiled, moved onto his hip and grabbed the back of my head as he pulled me into another deep kiss.
"I really do love you Drew," as Dave kissed me again.
I rolled over so we were spooning again with Dave on the outside. Dave leaned into my ear,
"So we're clear though, I'm not wearing any dresses......... but I might try the panties,"
"DAMN!" Was the last thing I said before we both fell back asleep.
Thank you to all those who have commented on the story, you have helped me tremendously with this chapter.
Please keep the comments coming, your comments keep me energized to keep writing.