Andrew's Adventures 10
The weekend went by fast as Dave and I had family responsibilities to do, but on Sunday evening the four of us got together to work out our invitations to the party. On Monday, we handed out the invitations to our costume party, mostly to kids who were either gay like us or knew Tom and Jem were gay and were cool with it. Nobody at our school knew about Dave and me, outside of Tom, so this meant most of the invitations went with Jem. Some went with Tom to hand out to kids at our school, and I did give invitations to Benny and JP from the play, as I had a hunch they would enjoy the party.
The party was for Saturday, and was to be held at Jem's house, as Scott and Mark agreed to host it, but had three stipulations. One, the invitation had to be returned at the door with a parent's signature, confirming the parent knew of the party and that their child was allowed to attend. Second, there was to be no drugs or alcohol at all, which was fine by all of us. The third and the final stipulation, the four of us were to be responsible for the party, which meant we were to control it. Everyone was to have fun and be safe, and if at any time the party got out of control, it was on us to bring it back, as well as fix or replace anything damaged. Mark made it a point to note the cost of certain mechanical parts of the hot tub, which had Tom, Dave and I, white with fear as we could never afford such things. Jem rolled his eyes at the whole speech, saying he had heard it a million times.
On Monday afternoon I was in the library wearing my soccer shorts and t-shirt, studying my lines for the play, before soccer practice. I had picked a spot in the back of the library, where no one could see me, or hear me, as I wanted privacy to move around the table as I pretended I was on stage saying my lines. It wasn't like it was hard to get privacy, it was after school, and I was the only person in the library, outside of Mrs. Cook the school librarian. I was waiting for Dave, as he had said he would practice with me, but so far he hadn't shown up. I was lost in the words of Juliet when Dave walked up behind me unseen. His hands went to my hips, as I jumped in surprise.
"Shit you scared me," I said as he kept his hands on my hips, and kissed my neck.
"Sshhh" was all Dave said as his right hand slid into my white nylon soccer shorts, and his left hand traveled up and under my t-shirt.
"Ahh, Dave, what are you doing, no not here, oh babe, mmmmm." My hands had gone to the table to keep my balance, as Dave pushed his crotch into my ass.
"Sshhh."
Dave's hand found its way into my white briefs and started fondling my quickly rising dick.
"MMMMM, babe please someone might see us, please you have to stop, oh God."
Dave's hand slid from my cock, which was now rock hard, around to my ass where he pulled my shorts and underwear down to just below my cheeks.
"Dave, Dave what are you doing, stop, oh huh huh, please, mmmm."
"Ssshhhhh," Dave said as I felt his lubed cock touch the walls of my ass, as it slid towards its favorite spot.
"Babe, babe, paaleeaaasssssse, ohhhhh."
My pleading was landing on deaf ears, as Dave's cock touched my hole. I was scared someone would see us, and the word would get out quicker than I could pull up my shorts that we were gay. And that was only half my concern, because if someone did see us we were surely expelled for this. I knew we should have stopped, but the possibility of being caught, and the pure animalistic lust Dave was showing as he took control of the situation were more than my logical brain could handle, especially once his cock spread my pussy open.
"Dave Dave Dave, Jesus, Oh God, mmmm, hhhssssss, uuhhh." I had to bite my lip as his lubed cock entered my boy hole with a slight twinge of pain. Dave slowly entered me as if he knew what I was feeling, which only added to the eroticism of the moment.
"Ssshhh, babe, we don't need Mrs. Cook spoiling the moment."
Dave was slowly pumping in and out, but with force as he would smash his groin into the cheeks of my bubble butt, driving me forward, making me grab the table to keep my self from slamming against it. The sex was hot and it felt so good, as the tip of his dick pressed my boy button over and over again. Dave took his right hand off my hip and slid it back under my shorts and briefs again, grabbing my prick as he began slowly stroking it.
"Oh Dave it feels so good, please, oh yeah, yeah, mmmm fuck, shit shit, I can't, huh, you need to stop, I'm going to cum in my underwear if you don't."
Dave was driving me on to the tips of my toes with every thrust, as he took his hand off my dick and pulled the front of my shorts and briefs down so the waist band was tucked under my balls, but since they were already lowered in the back they quickly fell to around my ankles, leaving me naked from the waist down. Dave moved his hand back to my cock and resumed his pumping of my cock.
"Uh uh uh uh uh, mmmmmm, oh boy, oh boy, oh boy, OH FUCK," I moaned as quietly as possible, as my cock shot forth a rope of cum all over the table in front of me. My eyes were rolling back as I was over taken by my orgasm. I barely heard Dave say the word fuck before launching his sperm into me, which made me clamp my mouth shut and grind my teeth, as I fought back the desire to moan out loud.
Dave kissed my back and shoulders as his cock slowly shrunk and slid out of me. Once Dave was free of my hole I quickly grabbed my underwear and shorts and pulled them up, as I turned for the first time to face Dave.
"Babe you were lucky we......"
Dave stopped me mid sentence as he pushed me back so that I was sitting on the table as he kissed me hard. I could feel the cum that was pooled on the table soaking into my shorts, adding to the wet spot forming from Dave's cum leaking out. I finally broke the kiss, a little pissed at Dave, as I shoved him back.
"Damn it Dave, what am I going to do now, I can't go to practice with cum stains all over my shorts and underwear."
"Don't worry babe, I have an extra jock and pair of shorts in my gym locker you can wear. And I'm sorry, don't be mad at me. It's just that after watching you fuck Jem in the hot tub the other day, I've been dying to fuck you standing up like you did Jem, and well I saw you here swinging your perfect ass in your cute little soccer shorts, and well I couldn't resist, please don't be mad."
"Babe, I'm never mad when you make love to me. I love it too, especially when you're driven like that. You just need to be careful; we can't get caught doing this kind of stuff."
"You're right, I'm sorry...But you know you liked it, especially the possibility of being caught." Dave said with a dirty little smile.
"Uh Hum, Excuse me boys are you two done back here, as I would like to close the library and go home if that's ok?" Mrs. Cook said.
Dave and I both jumped, as we nodded and quickly grabbed our stuff and ran out of the library.
"How long was she standing there?"
Dave was laughing as we ran to the boy's locker room, "I don't know, but I am pretty sure she didn't miss the huge wet spot on the back of your shorts, they're almost see through."
"What?"
On Tuesday Scott had been introduced to Mr. Heid, and they hit it off big time, as Mr. Heid was ecstatic to have Scott helping with the clothing. Thursday was our first real rehearsal, and Mr. Heid asked JP, Benny and me to come dressed in a dress, as we would need to get used to acting in them. Mr. Heid suggested we dress as far as we were comfortable with, and that each week he would assist us in adding the layers necessary for the parts, such as make-up, wigs, and appropriate body enhancers to look the parts.
This is what I had been waiting for, so there was no reason to pretend to step it up gradually with what I was comfortable with. I was comfortable with it all. I would just tell everyone that my mom had helped me get ready and that Dave's sister provided the clothes, with Dave backing my story. So on Thursday, after school had been let out and I had finished my soccer practice and showered, I found a teachers bathroom and entered it with my bag of clothes and accessories. I had decided that my light pink summer's dress was the best fit for today. Every other dress I owned was either too formal or too slutty. The light pink floral cotton dress with buttons coming from the collar down to a cute little hand tied bow at the waist, and stopped three inches before my knees was perfect for this occasion, as it could easily be one of Becca's dresses. I had Becca take my blond wig and braid the sides so they wrapped around my head in the style worn by women of the Elizabethan times. I put on regular boy cut white panties, my white padded bra, falsies and slipped into a pair of flats, before heading for the theater room. Normally I would have put on my make-up, but that didn't fit with the story I was giving, that Becca and my mom helped me with the outfit, and I really didn't have the time to do it anyway.
Dave was waiting outside the bathroom for me as he wanted to walk with me to the theater; his reason was to make sure no one gave me trouble. The rumors of the all boys Romeo and Juliet play had surfaced and the gossip had started to spread, but Dave and Tom did a pretty good job squelching them, as they were pretty high up in the social class of popularity, even though they were only freshman. That was a gift given to Dave from Steve as his popularity carried clout for Dave with most of the seniors. And with Dave in the production, few were ready to stand up to him and call him gay to his face, but there were always a handful of kids who felt the need to try and elevate their social status by picking on those whom they deemed weak. I personally think Dave wanted to walk with me because Mr. Heid had suggested Dave get used to performing in tights, like he had suggested with our dresses. And believe me when I say, Dave looked good in his brown tights, as I slapped my own hand on more than one occasion from grabbing a handful of his beautiful rump. But you could tell Dave was very uncomfortable in them, as he kept pulling his t-shirt down to try and hide his quite noticeable package.
When we entered the theater, most of the other performers were already on stage acting out some of the scenes, but when we got closer, you could have heard a pin drop.
Mr. Heid was the first to speak, "Wow Drew, you look wonderful, a um, I mean that is you look like you did your homework, I think we picked the right person to play Juliet."
"Thanks Mr. Heid." I said as I gave him my rehearsed speech of who helped me and how I got the outfit.
As Dave and I took the stage you could still hear the silence, as we separated and went towards the groups we would be rehearsing with for act 1 scene 1. Mr. Heid wanted to work with the three boys who would be playing the girls parts so we stood together at first. As I stood next to Benny and JP, all of us silently evaluating each others outfits, I couldn't help but notice the vast difference between these two boys. 16 year old Benedict Bell was as short as me if not a hair shorter and a bit over weight, which probably added up to why he was a shy kid. You could tell that Benny, as everyone called him, didn't make it into the sun much, as his skin was a pale white. His hair was like Tom's and a lot of other boys in this town, a short buzz cut. Benny was wearing an old button up purple blouse and pleated skirt that he either got from his grand Mother's closet, or a salvation store. The colors and patterns were all over the place, but the natural curves of his body fitted the clothes well, as his small tits and wide hips made him look very much like a girl. His boy tennis shoes and white socks, made me laugh and added to the hot mess I would soon call a friend.
John Paul Hernandez II on the other hand, was a tall skinny Latino boy, with dark wavy black hair. He was 17 and a senior in school, but you wouldn't know it. As a matter of fact you wouldn't even know he went to this school if you didn't have a class with him, and even then you quickly forgot about him. It definitely wasn't his looks that made him so forgettable; it was the way he carried himself. JP kept everything to himself, his answers to questions were short and to the point, he never stop moving to talk to anyone, everything about him was a mystery; everything that is except how he would look in a dress, as the answer to that question stood before me. JP was wearing a nice thin shoulder strapped charcoal grey evening gown, which was a bit much for rehearsals, but still looked nice. My mind was struggling to figure out where he got the dress, as it fitted him like it was tailored. JP being a couple years older, I really didn't know much about him. I was pretty sure he wasn't dating anyone at this school. JP was in a nice pair of flats that matched the dress, even though the dress really demanded heels.
"Wow Drew, you look really good."
"Thanks Benny, Dave's sister Rebecca helped me. You guys look good too. I was wondering JP, where you got the dress?"
"A cousin let me borrow it."
"Wow, she must be really tall," I said as JP was at least 6'.
"Yep"
"Are those Rebecca's fake tits and all?"
"No Benny, I had my mom get them for me, as I figured I wanted to look as real as possible."
Benny was staring at my chest and I could tell he wanted to touch them, but knew he shouldn't. I was about to let him when Mr. Heid walked up.
"Very well done boys, I am pleased to see you were up for my challenge and have taken it head on. I wanted you to get use to wearing a dress, and you all have accomplished that with what you're wearing and I commend you. I know it probably wasn't easy for you to find these outfits, so I want to let you know that for this play you won't have to worry about making or getting your own costumes as we are very lucky to have a gentleman who used to work on Broadway doing them for us. And even though some of you," as Mr. Heid looked right at me, "Are wearing a woman's bra, the women of Elizabethan times didn't wear bras as they weren't invented then, so none of you will need to wear them. And while we're on that subject, Drew, while those are really nice chest enhancers, and I hope you didn't spend too much on them, the corsets of that time period really smashed the women's chest down, so I don't think you will need them, but thank you for jumping into this roll with so much effort and thought. That goes for all of you; you really are brave for doing this. I believe in my heart you will be better young men for doing so, as it is a special gift to spend some time in the shoes of the other sex, to begin to understand some of the qualities that makes a woman, and to go where other men fear. These lessons you learn today will stay with you the rest of your lives."
Mr. Heid gave his speech with such energy, you really felt moved, so much so that I wondered if he had ever worn women's clothing. The rehearsal went fine as we worked on our lines and our movements on stage. At times I did feel self conscious about my outfit choice, as from Mr. Heid's point of view from below the stage; I was certain he could see right up my skirt and see my white panties. To make matters worse, every time I looked at Mr. Heid, he'd simply smile and wink at me.
On Friday, Dave met me at my house as we performed our usual routine, as we had everyday since we started it. It wasn't always a 69 before school; sometimes if either of us had spent the night then we would swap blow jobs in the shower as we got ready, or on one occasion Dave still had homework to finish so as he worked at the computer I sat between his legs and serviced him, only to have him service me on his bed, this morning we were running late and so after getting fully dressed I drop to my knees in front of Dave and pulled his cock through the fly of his pants and sucked him hard and fast, and no sooner had his load entered my mouth, Dave was on his knees pulling my dick out returning the favor. As soon as my cock was in my pants we scurried off to school. Dave informed me he had to pick up his costume and that he would be a little late to Jem's house tonight to set up for the party as we promised we would. Dave still wouldn't tell me his costume, even though had told him mine, which was Marilyn Monroe.
Saturday finally arrived and, my excitement was at an all time high with anticipation. My parents knew of the party, but they didn't know it was a costume party. The plan was to head over to Dave's house and get dressed, turn on the webcam and show Josh and Sean our outfits and talk to them for a bit, as we did a couple nights every week. Then Tom would pick us up and we would head over to Jem's and hour or so early to help with any finishing touches.
When I arrived at Dave's house, Mike met me at the door dressed in his usual golf attire,
"Party tonight huh sport?"
"Yeah"
"You two have fun, and be safe. The last thing I need is the cops calling me to pick up my son and his boyfriend, because they were shit faced and wearing women's clothing." Mike said as he laughed at his own joke."
"That's funny, I would have thought you would have liked the police station seeing as you and the cops have the same fascination with restraints." I said returning the laugh.
"I see my son and his smart ass attitude is rubbing off on you."
"Yes he rubs off on me almost every night; I just hope I don't get pregnant."
"Well if you do don't call me," Mike said as he left the house laughing.
Dave had told me to knock before coming in so he could surprise me with his costume. When I knocked, and Dave opened the door, I was swept up in mix of emotions as my teddy bear stood before me in his Cleopatra outfit. I laughed a little, as the idea was funny, but there was nothing funny about how sexy he looked in it. Dave was wearing a black wig with long strands that reached the middle of his back and bangs that framed his forehead. The wig was entwined with gold ribbons, and a golden headdress, with gold and jewel-encrusted snake medallion in the center. Dave's dress was a pullover turquoise blue dress that had gold thread woven into the shimmery material. The dress ended mid thigh, showing off Dave's smooth legs. The bust was embellished with circular sheer patches and gold sequins which also decorated the cowl-like neckline of this dress. The centers of the circular patches were open to revealed Dave's wonderful chest. Attached to the back was a sheer cape that draped from his shoulders and stopped just above Dave's ass. Attached to his arms were shiny gold fabric wrist bands and the two shiny gold arm bands. Dave wore an open toed gold sandal which laced up his legs with gold ribbon and decorated with matching leaves. Gold looped ear rings, necklace and a snake arm cuff finished the outfit.
"So what do you think? Is this like your dream?"
"You look really good babe, now we just need to find you some young naked boys to fan you and the picture will be perfect."
"Did you happen to bring two naked boys with you or are you just teasing me?"
"Look at you, already trying to get me into group orgy and the evening hasn't even started yet. And just wait the real teasing will happen when I am dressed."
"Sounds good to me, but just so where clear though, you are ok with a group orgy right, just in case I find two naked boys."
As I was heading to the bathroom to change, I turned and looked at Dave, "You know the answer to that question."
My outfit was known by every man, straight or gay, in the free world, as its picture was printed a million times if not more. Marilyn Monroe, standing on a windy subway grate, as her white halter dress blows up in the wind. I was sure I wasn't the first boy to dress up as Marilyn Monroe, but I wanted to feel sexy tonight and this costume did just that. And if I don't mind saying so myself, I looked HOT, from my blond curly wig and fake black mole, all the way down to my white open toed heels. I finished the make-up for both of us as, Dave turned on the web cam. Josh and Sean couldn't talk long, but they praised how we looked and wished us a great time, as we signed off and called Tom to pick us up.
Dave and I were about to mess around in his room when there was a knock on the door. Dave looked puzzled, as Becca was out with Brian and we knew Mike had already left.
"Who is it?"
"Hey bro, it's me, can I come in?"
"Oh, yeah sure"
I was mixed with excitement and anxiety, as I hadn't seen Steve since the drive-in theater evening, but I didn't want to seem too excited to upset Dave as I knew he was a little jealous that I had gone out with Steve.
"Wow, look at you two. Where's the party, and can I come?"
"It's at a friend's house, and of course you can go, if you can find a costume. Wait, what are you doing here anyway?" Dave said as he got up and hugged his brother.
"Dad didn't tell you? I'm down for the weekend while the school does some renovations on the dorms."
"So what kind of costume party is this? And can I really go?"
"Well, the theme is that boys need to dress as girls and vice versa; and hell yeah you can come, if you can throw something together."
"Well, it's not exactly on the top of the list of things to do, dressing like a girl and hanging out with a bunch of 15 year olds, but based on how you two are dressed, it sure looks like fun, and I have nothing better going on, so sweet, I'm in."
"Drew, you think you might be able to help me with a costume."
"Absolutely."
Not fifteen minutes later Steve looked like an honest to God street walker or prostitute as we called them here. He had to squeeze him into some black heels I had bought for Dave, but the rest of the costume fitted him well. We tailored a pair of his old worn jeans into a pair of short daisy dukes, followed by a pair of fish net stockings which I had in my collection, which ripped as soon as Steve pulled them up his strong legs, as I knew they would, but it only added to the over all image. Steve wasn't ready to wear panties and opted to throw on a pair of briefs instead. He did however wear a black bra, which I filled with some more stockings, as Dave and I were wearing my only two pairs of falsies. I finished the outfit off with one of Mike's large white button dress shirts, which I left open to reveal Steve's chest and black bra. I also pulled one of the corners of the shirt off Steve's shoulder to reveal even more flesh and then rolled and knotted the bottom of the shirt to show Steve's belly button and happy trail. With the outfit done, I threw on my brunette wig and some thick red lipstick and eye shadow, and a couple large loop ear rings I borrowed from Becca. All in all Steve looked like a real tramp, but for fun we stuffed some money into his bra to cap the outfit off.
Tom picked us up, as we made the introductions and headed to the party. Tom knew of Steve from school, but had never met him. Tom was dressed as Wonder Woman, with his red leather boots, his blue with white star's speedos, and red and gold leather top, he looked ready for action, and I could only imagine how the whip that came with the outfit was going to be used tonight.
Jem answered the door, as we all stood on the front porch, wondering who was watching the site of four teen boys dressed in women's clothes. Jem was dressed as Superman, with a sports cup on to make the focus of the costume his groin, which made me laugh, as I got the humor right away.
"I new you would get it baby doll, that's why we're best friends."
Dave looked at me confused as I had to explain to him, Jem always dresses as a girl, so if the theme is to do opposites, then Jem would dress as boy or man.
Jem took a quick liking to Steve as we prepped the house for the party. Mark and Scott were dressed as Sonny and Cher, with Mark being Cher and Scott being Sonny, for the same reason, Jem was Superman.
At 6 the party was off and running as guest arrived in all sorts of costumes. At a little after 6:30 Benny arrived and I was blown away. Benny came dressed as a belly dancer, and what a hot little chubby belly it was. He was dressed in what looked like a two piece red bikini, with silver quarter sized medallions dangling all over both garments. The bikini bottom was wrapped by a red chiffon skirt, which blurred the bikini and his bulge, which I was definitely trying to look at, as the chiffon skirt was such a tease to the eye. His belly, small boyish tits, and large bubble butt were plump to say the least, but the outfit accented them well. Dangling from his ears were large silver looped ear rings and his head was covered by a red chiffon material, giving him an almost gypsy look. His make-up was thick and clearly done by someone without experience in applying it, so one could only conclude he did it himself, which made him even cuter. His small feet were bare and adorable, and made me wonder why I had never noticed feet before. The little finger cymbals finished the costume off.
"Hi Benny, thanks for coming. You look amazing."
"Um thanks Drew. And thanks for inviting me." Benny paused for a second as he looked me up and down. "Wow you look really hot, I wish I had someone to help me with my make-up."
"I wouldn't worry about it Benny, you're pretty hot yourself."
"Thanks. I figured go with what you got, you know." He said as he gave his belly a little jiggle.
"Well it works."
"Is this your place?"
"No this is my good friend Jem's place; he's around here somewhere, look for the Superman costume."
"I thought boys were to come dressed as girls?"
"Well yeah, the idea is to come as the opposite sex... and well Jem kinda sees himself as a girl, and so..."
"You don't have to tell me anymore, I get it."
As I was pointing out where the drinks and food were to Benny the door bell rang. Since we had yet to leave the front entry, I got the door. Standing on the other side was JP, or at least I was pretty sure it was JP, as the person before me was dressed as Catwoman, with mask and all. The costume was a full body skin tight suit made of a light purple lycra material. His hands were covered with black leather gloves that went to his elbows, with nails to look like cats nails on his fingers. Knee high black leather boots and a black leather mask, complete with ears, finished the body of the costume. The final touch was a two foot black tail coming from his rear end.
"JP?"
"Yep. Thanks' for inviting me, nice outfit Drew."
"Thanks, yours is nice too. Really nice."
"Thanks; you look good too Benny, nice costume."
"Thanks JP; Wow, you're smokin hot in that costume."
Both JP and I looked at Benny after his comment.
"I'm sorry, did I go too far, I just meant your costume looks cool, that's all."
"Don't worry about it Benny, you were right the first time, JP does look hot in that costume."
"Jeeze guys, a... I... a don't know really how to comment on that, a I guess thanks."
We all separated with me making a mental note that Benny was probably gay like a lot of the kids at the party. JP on the other hand was a puzzle I just couldn't get a read on. Did he like boys; maybe he liked girls; maybe he just really excelled at dressing up like one. I had no idea and it was driving me nuts. The party was in full swing as everyone seemed to be having a great time. At about two hours into the party Benny found me and asked if he could talk to me for a second. I excused myself from the conversation I was having and walked with Benny as he led me outside where no one was around.
"Every thing ok Benny, are you having an ok time?"
"I'm having the best time ever, I it's just, um, a well," Benny looked around to see if anyone was in ear shot, "Um a lot of people here seem to be gay, and well I was wondering if you invited me cause you think I am?"
"Oh, well yeah I guess most of the people here are gay, is that a problem?"
"Oh no, but did you think I was gay. And um are, are you gay?"
"Yes Benny I am gay, and I haven't told a lot of people, so I hope you can respect my wishes and not tell anyone. As for whether I thought you were gay...No, I just thought you would enjoy the party, as I knew you didn't mind dressing as a girl."
"Oh ok," Benny said with a little disappointment in his voice.
"Does that disappoint you?"
"Not really, well yeah I guess it does kinda...It's just, well, I am gay, and I was hoping you invited me because you liked me or something, cause I really think you're cute and all."
Benny was blushing a new shade of red when he said that.
"Wow Benny, that is really sweet, thank you, but I have a boy friend. But if I didn't, I sure would hang out with you, because I think you're pretty cute too."
"Really, you think I'm cute?"
"Oh hell yeah, you have a sweet ass, and while you're not ripped or anything, it kind of works with your face, and gives you a really sweet and innocent look, something I find really hot."
"Wow, no one has ever said I was hot... So it's Dave huh? Dave's your boyfriend?"
"What, oh, um, uh, yeah, how did you know?"
"Well you two are kind of all over each other, but at first I thought it was just you two being really close friends and all, but after you said you had a boy friend, it all kind of made sense, and it had to be him. Plus you two look happy when you are together."
"Yeah, I am happy." I said a little too enthusiastically, as Benny's expressed sadness.
"Don't worry Benny there is someone for you out there I am sure."
"Thanks but you don't have to say that, I know you're just being nice and all. But lets be real, you know I'm shy and clearly over weight, and nobody even notices me, unless they're calling me Buddha Benny. I was just hoping since you're kind of shy like me, and well, I think you're cute and all, a... never mind, I've said too much."
Benny started to walk away.
"Wait Benny, I meant it when I said you're hot looking, and well, maybe I can help you out. I know most of the kids here; maybe I could talk to someone for you?"
"Really, you'd do that for me?"
"Yep, anything for a fellow thespian."
"Well if you're offering," as Benny spun around, " and pointed to a guy standing next to the hot tub by himself looking out of place, "Who's that, and is he gay?"
I chuckled a little, "You like him huh? Yeah I could see that."
"Yeah he's hot. I don't know why he is all alone, especially dressed like that, but damn he's cute. Probably way out of my league though."
"That's Steve, and yeah he is pretty hot. And today Benny is your lucky day, as he is a good friend of mine. He's older and bisexual, but I know he's recently single, although I am not sure he's looking for anything steady, but I can ask."
"Yeah thanks, if you don't mind."
Benny's smile had returned, even though I knew there was a good chance Steve would blow him off, but it never hurt to ask. I mean Steve found something in me he liked, so who knows.
I walked over to Steve and asked him how it was going, and if he was having an ok time, which he said he was. I then talked to him about Benny, as I pointed at the shy looking kid. Not completely surprised, Steve did seem interested, and said sure he'd talk to the kid for me, which made me feel really good, but he did give me one condition though, that he could come back some day and use this cool looking hot tub. With the way Jem reacted around Steve when they were first introduced I knew this was a no brainer, as I agreed quickly.
I left my conversation with Steve to find Dave and see what he was up to as I hadn't seen him in while. When I found him he was the living room talking to a tall kid from the school basket ball team named Jake. Jake was 6'-7" and played center on the team with Tom and Dave. He was built similarly to Tom, as he was tall and lengthy. His hair was a little longer than mine, as he kept it short, but was still long enough to comb. What really made him stand out were his cute freckles that splattered his face, and one could only imagine the rest of his body. Tom and Dave had told me Jake was bisexual. Even though at school he had a girl friend that hung all over him.
"Hey babe," Dave said as I walked up.
I shot Dave a questioning look for his use of words in front of Jake, as I approached.
"Don't worry babe, Jake knows about us, and he's cool."
"Oh ok, is there anyone who doesn't know about us?" I asked semi kidding.
"Jake was just asking me about JP, and wondering what his story is about. You think he's gay?" Dave asked me.
"I have no idea; I have been scratching my head on that one."
"Well I sure would like to find out; I mean straight, gay, bisexual, whatever, when you come dressed in a skin tight leather suit like that, with a body like that, damn." Jake said burning a hole into JP's ass, as JP played a game of nine ball by himself.
"Go get him cow girl," Dave said as Jake was dressed as Jesse from the Toy Story movies.
Dave and I mingled some more as the party started to wind down. The only one's left were trying to finalize their moves on someone or closing the deal and making out in a random corner of the house. Jem and Tom had long since disappeared and I smiled when I saw Steve and Benny chatting it up like good friends, and standing awfully close to each other. The night had been a huge success, and people were commenting on how much fun they had had. I myself had to agree, as seeing all those boys in women's costumes had me super randy and needing of a good fuck.
I leaned in and whispered into Dave's ear, "Hey babe, do you think Cleopatra would be interested in showing Miss Monroe her serpent? Cause Miss Monroe sure would like to play with something long and thick."
"Would she now?"
Dave turned and excused us from our conversation as we headed up stairs to find some privacy. There were multiple rooms on the second floor, including Jem's room and the master bedroom where Scott and Mark were currently hiding. Also on the second floor was the spare bed room where Jem had said we could stay for the evening, and where we were currently headed. In all honesty we weren't really paying any attention to the closed door as Dave's tongue was in my ear and his hands were working there way up my skirt, but when we opened the door to the room, and saw Wonder Woman, holding Superman up against the wall with Superman's bare legs wrapped around Wonder Woman's hips as Wonder Woman drove her large dick into Superman's ass; well you kind of stop what you are doing and stare, which is exactly what we did.
Tom had Jem off the ground with Jem's legs wrapped around his hips, and his back pressed against the wall as he long dicked Jem's boy pussy. Jem had removed his blue tights and red speedos, but had kept the skin tight shirt, cape, and red leather boots on while he was getting pounded. Tom had lowered his shorts, which were around his ankles, as he was fucking the life out of Jem, or least that's how it sounded. Jem had his eyes closed and his hands on Toms neck as he bounced on Tom's rod. Tom had one arm around Jem's back and one on the wall for balance as he gave short powerful thrust with his hips.
"That's it baby oh yes, yes, uh, uh, uh, huh, huh, mmmmmmm, oh yes Wonder Woman take me."
"Oh fuck, your so hot babe, shit yeah, take it take it Superman."
Dave and I backed out of the room before we were noticed, and started laughing, "Take me Wonder Woman, take me." Dave mocked.
"Now that's something you'll never see in the comic books." I said as I pulled Dave across the hall, to Jem's room.
Dave and I figured that if they were in our room, we'd use their room, but we should have figured there was a reason they weren't using it. When we opened the door, there on the bed was another couple making out, only this couple was a couple of girls, and girls we didn't know, so we quickly left the room, embarrassed we interrupted them, but again laughing at the scene we saw, as the girls were dressed as a priest and an altar boy.
Dave and I laughed as we continued our search for a room to fuck in.
Outside Benny was talking to Steve,
"Drew said you just broke up with your girl friend huh?"
"Yeah, it was mutual though, we just weren't on the same page."
"That sucks, sorry to hear about that. I hope I am not being to forward, but I think she must have been an idiot to not want to be with you." Benny said rubbing one bare foot on the other. "But at least now I bet you're getting a lot of rebound sex... Oh jeeze, a um I'm sorry, I can't believe I just said that, that was really rude of me. I'm going to go." as Benny turned to leave.
Steve smiled and put his hand on Benny's shoulder, "Stop Benny, it's alright, you didn't do anything wrong. I wish I was getting rebound sex, but the truth is we broke up because she wasn't as sexually adventurous as I was, and well I've been kind of doing some soul-searching to see if it was me, maybe I'm the one who pushed it too far."
"Oh, well I don't have a lot of experience, actually not much at all, but I know there isn't much I wouldn't do. Oh my God, I can't believe I said that out loud, you must think I am such a freak."
"Just relax, you're fine, and actually I think you're kind of cute." Steve leaned in and gave Benny a light kiss on the lips.
Benny was shaking after the kiss, but it wasn't fear that over took him; it was excitement as he quickly leaned forward for another kiss. Steve was tickled by how randy Benny was, but put his hand lightly on Benny's shoulder,
"Whoa Benny, lets go find somewhere a little more private, what do you say?"
"Yeah, yeah ok."
Benny followed Steve to what looked like a either a shed on steroids or a small mother-in-law unit. The small white house was about the size of large bedroom, with windows on two sides, and a window in the door. The door was over sized, as Steve tried the handle.
"I can't believe they would leave this unlocked," Benny said.
"Why would they lock it, it's not like anyone could get into this neighborhood who wasn't meant to be here, and even if you did sneak in, you're sure not getting out with anything with all the security around here."
"Yeah I guess that makes sense," Benny said as Steve turned on the light.
You could tell the unit was for someone to stay in; as there was a table and chairs near a small kitchen, with a bed in one corner. One could also tell that Mark and Scott hadn't had anyone in here in a long time, as backyard items littered every corner. Tiki torches and patio chairs stacked in one corner, floating pool chairs in another, and miscellaneous rolls of fabric piled on top of boxes which had the words of every major Holiday written on them filled the rest of the space.
"Works for me," Steve said as he spun around and grabbed Benny and pulled him in for a kiss.
Benny returned the kiss as their hands began to roam each others bodies. Steve pulled Benny back to the bed, moving some boxes and rolled up Broadway posters, before sitting down.
"Are you ok with this?" Steve asked as he held Benny's hands, with Benny standing between his knees.
"I'm a little nervous, when I said I didn't have much experience, I really should have said I don't have any experience; that is with someone else anyway."
"It's ok Benny, we'll only go as far you want to go."
"Oh no Steve, that's not what I meant. I want to do it all, I want you to do what ever you want with me, it's, it's, I don't want to disappoint you, that's all. I mean, I'm sure you're used to hard bodied ladies who know what they're doing, and well I'm neither of those things."
"It's not like I didn't know this before we came in here Benny, and how do you know you're not exactly what I am looking for?"
"Really?"
"I'm here with you aren't I; now no more talking,"
Steve removed his wig, shirt and bra as he sat there in just his jean shorts and briefs.
"Why don't you do a little dance for me Benny?"
"Ok, but I'm not a good dancer."
"Shh, just dance."
Benny started dancing as he jumped all around, his chiffon skirt bounced all over the place, as his tiny chubby tits jiggled like a young teen girls. Steve put his hands on Benny's hips as he slowed Benny down, and brought him close enough to kiss his belly.
Steve moved Benny's hips in slow side to side motion, similar to that of a dance performed by an honest belly dancer. Steve then leaned in and ran his tongue around Benny's belly button, licking and kissing as Benny swayed his hips, Benny's hands on the back of Steve's head.
"Ohhh, mmmmmm."
Steve had never heard someone moan so loud and he hadn't even begun to get to the good part. Steve found it strangely exciting to hear Benny so into it. Steve ran his hands up Benny's thick legs as he realized they were hairless.
"I love your legs, are they the only part of you that is hairless, or is the rest of you hairless? Wait, wait, don't tell me, I'll find out for myself." Steve said with a dirty little smile.
"Benny was pleased with anything Steve wanted to do, especially the way his hands felt running up and down his legs. He really loved it when Steve's hands ran over his ass and moved up his back to the strings of his bikini top, where he felt Steve pull the string, and release it. Steve stood up grabbing the bikini top and raising it above Benny's head as he removed it and the chiffon head dress. Steve leaned in and kissed Benny's ear, and removed the clip on ear rings. Steve began kissing the nape of Benny's neck as he unbuttoned his jeans and let them fall to the floor. Steve, now only in his black Calvin Klein briefs and the torn fishnet stockings, began to lower himself to his knees, with the idea of showing Benny a pleasure he had never known, but Benny beat him to the punch as he dropped to his knees in front of Steve.
"Mmmm, uhhh, um, um, um, um," was the noise Benny made as he mouthed Steve's hard cock through his briefs.
"Fuuuckk, yeah, Shit Benny, suck me." Steve said a little caught off guard.
Benny's enthusiasm pushed Steve back so that his legs buckled by the bed and he landed on his butt. Benny didn't miss a beat as he crawled forward on his knees and grabbed for Steve briefs and pulled them down his legs, as the sight and feel of Steve's hairy legs quickened Benny's pulse and arousal. Benny had many fetishes, but they usually all involved him being a bottom to a well muscled hairy man, and Benny could think of no one more beautiful than the man in front of him.
"Tell me what to do," Benny said before kissing the large mushroom tip of Steve hard eight inches.
Steve tickled the palms of his hands with the bristles of Benny's short hair, as he lightly pushed his cock into Benny's mouth.
"That's it Benny, yeah, watch your teeth, ohhhh God, yeah Benny, mmmm, now use your tongue, yeah like that, ohh man, mmmm. Oh shit it's been too long."
Benny had been completely honest with Steve when he said he had never been with anyone before, but Steve had no idea of Benny's sexual hunger. Benny had been preparing for this day for years now, carrots and cucumbers had been his closest friends over the years, and they had prepared him well for what he was doing now, as he pushed Steve's cock deep into his mouth and down his throat. It was the warmth of real flesh that Benny was locked on, the pulse, as blood cycled through the large veins his tongue danced with. Benny was in heaven, the day he had waited for was here, and he was going to enjoy it.
"Shit Benny, oh damn you're good, oh shit umm, huh huh."
Steve was close and he knew it was but seconds from no return. He pulled his cock back, so that only the tip was in Benny's mouth, as the first shot splattered across Benny's tongue hitting the back of his throat. Steve pulled his cock all the way out and aimed it at Benny's face and the second and third shots hit Benny on the nose and lips. The rest of Steve's cum was aimed at Benny's tits as he let the less forceful shots drop and run across Benny's nipples. Benny was savoring the flavor of cum in his mouth as he smiled from ear to ear, loving every moment. Steve stood up and had Benny lie on the bed on his back. Steve bent over and began kissing Benny on the lips, smearing the cum into Benny's lips and mouth and he kissed him deeply. Steve moved to Benny's tits and sucked the quarter sized puffy cum drenched nipples into his mouth as his hands ran up and down the rolls of Benny's smooth belly. Steve could feel Benny's hard dick throbbing on his abs, as he licked every inch of Benny's chest, making sure to get all of his cum. He moved down to Benny's crotch, where he quickly removed Benny's bikini bottoms and was happy to confirm Benny was indeed hairless everywhere. Benny's dick fitted him well, as it was short and stout. Steve guessed it no bigger than 4.5"s, but as thick as his. Steve gave Benny's cock a quick lick as he work his way to his down to Benny's wrinkled sack.
"Oh hisssssssss, ahhhh."
Steve moved from Benny's cock and worked his way to Benny's virgin pussy. Steve dove right in, his tongue running over the wrinkled hole, circling its prey, worming its way in. Steve loved ass more than anything in the world. It was an obsession of his that had started at puberty. Steve loved looking at the asses of his fellow team mates in their tight baseball and football pants. He loved looking at his friend's asses in the showers when no one was watching. His love for ass didn't stop with just boys, he loved girl ass as well, and if you had a bubble butt you had Steve's attention. Steve knew it was his obsession that attracted him to Drew, and now Benny, but he also knew it was his obsession that had driven most of his girl friends away, as none of them could keep up with Steve. Steve was addicted and he couldn't get enough, and now spread-eagle before him was a young man offering his bubble butt freely, almost pleading with Steve to use it whenever and however he saw fit. It was his obsession that had Steve's dick pulsing hard again; it was Benny's instant trust in him and his young boy innocence that had his heart pounding.
"Oh, oh ahhhh, ahhhh, uh, uh , MMMM."
Steve removed Benny's calves from his shoulders and had Benny stand up and move to the end of the bed. Benny bent over and grabbed the iron footboard, as Steve grabbed some Hawaiian leis that were in a bag near the bed and quickly tied Benny's hands to the footboard. Steve gave Benny's sweet plump toosh a couple quick pats as he watched it jiggled. Walking over to the small kitchen Steve grabbed a bottle of hand lotion near the sink, and on his way back to Benny stroked his 8" cock with copious amount of lotion.
"I'm going to fuck you now Benny, ok? I'll go slowly at first so you can get used to it, but then we're going to fuck." Steve said more as a statement than a question.
"This is what I want Steve, just do it, just fuck me hard, oh damn I love this."
Benny was really shaking his rump now, like he knew about Steve's addiction, and was waving the drug in front of him. Steve put a hand on Benny's hip to stop the swaying, as he used two lubed fingers to prepare Benny's boy pussy. Steve pushed his cock into the valley of Benny's butt, leaving it at the entrance to his hole. Benny was lost in its warmth again, as he felt Steve lean over and kiss the base of his neck. Benny sucked in a mouthful of air as he felt Steve simultaneously nip at the skin of his neck and pop his cherry with his mushroom tip.
"Oh God, ow, ow, oh, oh, huh, huh, mmmmm."
Benny was moaning loudly again, and Steve was concerned he had pushed it too far, literally. Steve was about to back it out slowly, when all of sudden Benny pushed back, sinking most of Steve's cock into him. Steve would have buried it home had he known what Benny was about to do, but as it was, the sudden move pushed Steve back as well, as he held on to Benny's hips to maintain his balance.
"OOOOOHHHHH FFFUUUUUUCKKKKK, you're huge, OH GOD, oh shit, it feels so fucking gooood."
Benny had shoved many things up his ass before, so he was used to the initial sting of pain as something spread the rings of his love tunnel. Steve however was larger than most of those items and with those items Benny was always in control, and now he had none, and loved it.
Steve grabbed the iron footboard Benny was tied to and used it to pull himself deeper into Benny. He had missed the feeling of a tight hole squeezing and caressing his cock, as Benny spread his legs to allow Steve to get even deeper.
"Oh Benny, oh man, your ass is sweet. Oh Jesus, Oh yeah that's it."
Steve took a hand and placed it on Benny's tits as he squeezed and twisted the nipples. Benny was moaning and thrashing around, as the feeling over took his thoughts. Steve pumped Benny for a good 15 minutes, with each forceful thrust drawing a moan from Benny. Benny could feel his cum boiling, and knew he was going to explode any second.
"Oh fuck, fuck, fuck, I'm gunna cum, oh shit."
Steve took his hand off Benny's tit, and placed it on his chubby cock and started stroking as he continued to pound away at him. Benny's cum fired out and hit the mattress as his ass clamped down on Steve's dick. Steve stopped stroking Benny and grabbed the iron rail again and used it to drive Benny onto his toes with each powerful thrust.
"Here's my load Benny, take it, yeah fuck yeah take it uhhhh." Steve groaned as his cum sought refuge in Benny's pussy.
Steve let his slowly shrinking cock fall from Benny's hole, as he leaned in and licked some of the cum that dripped from his pussy and down to his balls. Benny was resting his head on his arm and breathing hard, as Steve walked around and scooped up what was left of Benny's cum off the bed sheets and rubbed it on his balls. He then laid on the bed on his back with his leg hanging over the footboard, and the looked at Benny who was watching him with a smile.
"Lick em babe." Was all Steve said as he looked at his sack.
Benny, still tied to the foot board, stepped up and leaned over and began licking Steve's balls as he nudged them with his nose, inhaling the smell of cum and sex.
"You, my sweet Benny, ohhh, are a Godsend, oh man, mmm"
Steve let Benny lick him clean for a good 10 minutes before he got up and released Benny. The two kissed and cuddled as they returned to the bed, both in a happy bliss, both beyond tired, as they quickly fell asleep, Steve on his back, with Benny resting his head on Steve's muscular chest.
Being more careful Dave and I checked the rooms as we went and found only one down stairs not occupied and it was Scott's tailoring studio. We knew we shouldn't go in there but we were too horny at this point to use logic. If the images of the kids in costumes making out was enough to get us to stop and stare then this room took the cake. Lining the walls were mannequins of various sizes and shapes. Most of the mannequins were dressed in an outfit you could tell Scott was working on, as the outfits were in multiple stages of completion. Those mannequins that were naked were really special, as Dave and I quickly noticed they were all male, and by that I mean all male, as they were anatomically correct. These mannequins, depending on size, all had a nice set of balls and a flaccid penis. We both shook our heads as Dave pointed at two mannequins which were dressed in what we could only assume were our costumes for the play.
"So you ok with an audience?" Dave asked as he ran his hands under my skirt.
"I'm Marilyn Monroe; I don't do anything without an audience."
"Than how about you use that pole over there and show me a nice little dance, Miss Marilyn."
I walked over to a pole used to hold up garments and wrapped my leg around the pole and spun around, as I put a finger in my mouth and began sucking. Dave sat on the edge of Scott's desk and watched as I did my best strip tease. I grabbed the pole and slid my hands down to the bottom as my white dress flipped up and exposed my panties and ass to Dave. I used gravity and a little wiggling on my part to shimmy out of the dress. Turning around in my panties and bra, I placed my finger into my mouth again and circled it around my belly button and then down to my pulsing cock, with one hand still on the pole as it split the cheeks of my bubble butt and ran up my back. It was the final straw for Dave, as he jumped off the desk.
Dave slid to his knees and slid my white panties off and began kissing my thighs. I held on to the pole as he worked his way to my balls. He kissed and fondled them with his tongue, as he slurped one at a time into his mouth. Dave moved me to the desk from his kneeling position, so that I was bent over the desk as his hand went back to tickling my nuts and his lips went to my hole.
"Oh baby, yes that's it."
Dave lovingly licked my hole spearing me with his tongue. Dave slowly worked from my hole until he was standing behind me. Dave pulled his skirt up, and revealed that he wasn't wearing any panties.
"How is it that no one notice your sword all night Miss Cleopatra?" I said looking over my shoulder.
"Well there was a hot Marilyn Monroe running around, and I think every boy was sporting a sword tonight." Dave said giggling.
"Good answer."
Dave stepped up and moved his cock to my hole.
"No teddy bear tonight, ok." I said, as I turned and grabbed the desk to brace myself.
"What ever Marilyn needs, is my command." Dave said as he pushed his cock into me.
"Oh baby, yes."
Dave did as I requested and skipped the normal pleasantries of making sure I was ok before pounding my ass. This time he simply stuck his dick in me and started pounding like a mad man, pushing me on to my toes.
"That's it baby yes, oh yes, fuck me, oh harder, harder, yes Ohhhhh."
Dave reached around and started stroking my cock, as his dick slipped out. Dave quickly slipped it back in to sounds of my heavy moaning.
"You like that babe, you want to be long dicked?"
Dave purposely pulled his cock all the way out and punch it back in driving me crazy. Every time his cock left my hole, it would spasm and start to close, only to be slammed back open by the force of his cock re-entering my ass.
Dave must have been horny as hell, because after only ten or twelve long strokes, Dave was babbling, "Oh Shit babe here it comes, oh fuck." Dave moaned as he slammed it in and held it deep in me, and deposited his warm seed.
Feeling his cock pulse in me was my trigger as my cock fired off 6 quick blasts.
Dave and I quickly finished and cleaned the room and left, not before examining the costumes for the play. When we made it back upstairs, we found Jem and Tom had made it back to their room and ours was left open.
Dave and I slipped into bed after removing our costumes completely.
"You are beautiful, you know that, I could stair at your body all day and night." Dave said as he dragged a finger up my naked hip. I pushed my butt back into his crotch, as I snuggled up closer into our spooning position.
"Thank you babe, you're not too bad yourself."
"No I mean it; I don't think you know how beautiful you really are. Everyone was talking about how good you looked tonight, and how they wished they had your looks, I was practically bragging to everyone that I was the one dating you."
"Wow, I knew I looked ok in the costume, but I didn't think I was anything to write home about."
"Babe you were more than ok looking you were smokin hot; and trust me when I say the things most of these horny boys here tonight wanted to do with you, is not the kind of thing you write home about."
"Well babe, you're the only boy I was trying to impress here tonight, but I hope everyone else had a good time."
"Well we know Jem and Tom did, and I am pretty sure Steve did, as I saw him holding hands with Benny, which makes me think Benny might be gay. And I know Jake had a good time, even though he didn't get to hook up with Catwoman, and we know the priest and the altar boy had a good time; who else was left?"
"Yeah I think you covered the important ones. And yes Benny is gay, and I am pretty sure your brother had a wonderful evening. Which makes me think, since everyone had such a good time, maybe we can do something like this for your Birthday party that's coming up?"
Dave leaned in and kissed my neck and ear, "I don't think my dad wants to see a group of gay teenage boys running around his house in dresses. Now we better get to sleep before I get my second wind, and you're unable to sit tomorrow."
"Well when you do get your second wind let me know, because I have something for you to blow; but as for being able to sit tomorrow, well I believe it's my turn to pitch next." I said giggling.
"I love your dirty mind," Dave said as he pushed his chubbed dick into the crevice of my ass, and promptly fell asleep.
"Basketball players, good for a quick sprint and handling balls, but no endurance." I said in a quiet whisper as I felt Dave's warm breath on the back of my neck. I fell asleep with the images of teen boys in dresses strapped to metal horses and leather swings in Mike's garage as Mike stood in the middle with a smile across his face.
Thank you again to all of those who have sent me wonderful comments on the story. Please keep the comments coming. Any ideas, suggestions, or criticisms are welcomed.
Sincerely,
Tony
Tfreitas91@yahoo.com