Going Both Ways
Copyright© 2010 by Everydayguy
Chapter 2
Erotica Sex Story: Chapter 2 - A story with continuous sex about a guy who goes both ways. AC/DC - Bi-sexual - Marches to a different drummer. If you don't like lots of sex, this is not for you. If you are homophobic, you'll hate this one. This story is for other sex addicts who enjoy reading with one hand in their lap. Dean, learns about sex and himself in his formative years then enjoys sex with any and all. Happy stroking.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa mt/ft ft/ft mt/mt Consensual Romantic Gay Lesbian BiSexual Heterosexual TransGender Sports Incest Brother Sister Swinging Gang Bang Group Sex Orgy First Safe Sex Oral Sex Anal Sex Masturbation Squirting Water Sports Enema Cream Pie Exhibitionism
When the alarm went off I sat up. The first thing I noticed was no roomie, oh well.
I put the towel back around me and headed for the shower with my toothbrush. After a couple big glasses of water, I did the shit, shower, and shaved the few whiskers I had. Back in the room I dressed quickly, straightened the room, grabbed my backpack and headed for the stairs.
Dan and Jake were waiting for me with another guy they introduced as Jim. He was also on both the football and wrestling teams. As we walked to the cafeteria, Dan intimated that Jim had the same interests as they did. When I smiled, Jim asked, "Do you swing that way too? You know, like cock too?"
Dan said, "This is a true bi-guy. The man loves pussy but enjoys playing with dicks just as much. Perhaps you can see some of that tonight. Come by about nine tonight. But be nice now, we're going to eat breakfast with my sis and her roomie."
Jim said, "Those are the softball players right?"
"Right. Dean here is messing with both of them so be nice and don't be too overboard."
"Not a problem," Jim said. "I like the way Dean looks though. I bet he's a good fuck."
Jake said, "Like you wouldn't believe."
The four of us found Jill, Mary, and two other girls from the softball team waiting for us. All eight of us went through the line together, flashing our cards at the register. The coaches checked that we ate regularly and what we ate so they knew whether we were keeping to the diets they had specified. Mine was just heavy, all I could eat, whenever I could eat.
When we sat, I was between Mary and Jill with the two other girls across from us. Jill said, "This is Sandy and Kathryn, team mates of ours. Sandy is a good bat and plays mostly outfield and Catharine is one hell of a catcher. We've been telling them about you and they want to visit with us later. Would you mind showing off for these two?"
Dan was sitting next to Kathryn and asked her, "You know, you and I could do some showing off ourselves. What do you think if I should join you guys later?"
Jill remarked, "Oh my, brother has the hots for you Kathryn. If you have him over, you're in for a treat."
Kathryn looked sideways at Dan and said very softly, "You would rather come play with us than stay with cute Jake?"
"There are times," Dan was grinning, "when only the female form will make me happy. With your form, I think you would make me very happy."
I noticed Kathryn's left hand wander into Dan's lap. He had a shit eating grin on his face as she groped him. She spoke again but even more softly, "If what I feel is real, I want to see what I can do with that thing. When Dean comes over to Jill's, come along. I think we might have a party going."
Our classes were about the same. By the time we were in the workout room, I was ready to let some steam off. Since I didn't have an afternoon class, I had time to finish all of my assignments and had been in the batting cage for over an hour. The batting coach spent the last half hour with me working on delivering more power to the ball.
After supper, Dan, the four girls, and myself went to Jill and Mary's room for some fun. This time, Jill and Mary were more laid back. However, as soon as Kathryn and Dan were inside the room, Kathryn was giving Dan a full body press while trying to reach his tonsils with her tongue.
Kathryn told Sandy, "Uncover the goodies baby to see if he's as big as advertised. It sure felt like it this morning."
So while Kathryn was taste testing Dan's lips, Sandy was getting Dan out of his clothes. As we lay on Jill's bed watching the action, Mary was playing with Jill's breasts. Mary kept it up until Jill just pulled her top and bra off. Mary looked at me and said, "Help me get her naked. You can watch for a while."
There was too much to watch. Dan was being treated to some licking by Sandy and stroking by Kathryn. I could see his knees buckling before the girls maneuvered him to Mary's bed. Kathryn was a big girl, and had Dan on his back straddling him. She raised up and began trying to stuff his gigantic cock into herself. Dan was trying to be responsible and asked, "I have rubbers, shouldn't I use one?"
Kathryn said, "I'm protected from your mean bad sperm. Shoot it in me, on me or all over me and it can't hurt me. Are you gonna fill me up with it?"
"Pretty damn soon, You're too hot for me to last long."
"Oh baby," Kathryn said, "you say the nicest things."
About that time, Sandy straddled Dan's head and planted her steamy pussy on his mouth and tongue.
Meanwhile, Mary was chowing down on Jill as if we didn't even have supper yet. I thought I would be helpful and pulled all of Mary's clothes from her. Once that was completed, I buried my face between the glorious cheeks she was displaying. That made her double her efforts eating Jill who was moaning "more" over and over again.
I heard the trio on Mary's bed all grunt about the same time. When I glanced over at them, Sandy had her face in Kathryn's now soupy pussy while Dan was laid back with a satisfied look on his face. His monster dick was flopped over on his belly.
When my two girls had come crazily, I pulled both to me and held them. Mary was giving me Jill tasting kisses as Jill was kissing my nipples and stroking my hard on. She leaned over me and gently squeezed my balls as she sucked me into her mouth. That was about all the stimulation I needed as within a couple of minutes, I attempted to push Jill's mouth from me.
She refused and kept sucking letting me fill her mouth with my first load of the day. When I was finished shooting, she leaned over Mary and let my creamy load dribble into her mouth. That is so nasty.
Jill got up on her hands and knees and said, "Now fuck me, shove that wonderful dick up my wet pussy."
I was no dummy and immediately complied with her demand. As I was beginning to get a rhythm going, I felt small hands pulling apart my cheeks then a tongue probing my butt hole. That will speed up the sperm production. I looked behind me to see Sandy tongue deep in my butt with Mary on her back sucking on Sandy's pussy. Man, these girls were an orgy waiting to happen.
There was a lot of moving around and I saw that Kathryn wanted to get a mouth on Mary who was sucking Sandy who was rimming me. As soon as Kathryn latched onto Mary, Dan got behind her and lined up to plunder the already well used hole.
The stimulation was more than I could handle and I blew my load deep into Jill as she was stuffing a pillow into her mouth to keep from screaming.
When we settled down from that combination, Sandy was licking on my dick getting it to stand up once more. When it was pointing skyward, she straddled me and said, "It's so much nicer to have a real dick to ride instead of one of my plastic ones. Katy, get Dan back up so I can feel him too. You can sit on this one a few minutes before he launches another gallon of man juice."
When Sandy and Kathryn swapped dicks, Kathryn said to me, "You better get with it and come or you're going home with blue balls. It's already eight thirty."
Jill leaned down and gave me a kiss then planted her pussy on my mouth. She was saying, "Suck that stuff out of me stud. You put it there, now suck it out."
The stimulation of eating Jill, Kathryn riding me, and Mary playing with my balls was all that was needed. As I was shooting stream after stream into Kathryn she moaned, "Oh Dean, I can feel you shooting in me. Oh wow, that is so neat."
Jill and Mary gave me some sweet kisses as I tried to dress. Dan was having the same kind of trouble on Mary's side of the room. We were finally clothed at ten to nine and were getting ready to leave when I heard Kathryn ask Dan, "Can you come to our room tomorrow night? You and I could have a private party if you want. You'll still have time to get your dorm room to play with your boy toy."
The two shared a kiss as Jill and Mary made sure I would meet them in the morning. Jill said, "Mary's gonna have her work cut out for her tonight. I'm still so horny I could take on the whole softball team."
Mary said, "You'll have to spend more time satisfying the insatiable Jill tomorrow night. She gets like this sometimes but we've never had a real dick to help cure her itch. Dan comes by sometimes but he can't keep it up with his sister. Imagine that."
Dan and I strolled back to our dorm. He accompanied me to my room so I could drop off my backpack. We went to the next floor and he let us in with his key.
When he locked the door and turned on the light, there was Jim and Jake laying reversed in a sixty-nine sleeping. Dan grinned and said, "Now isn't that a sweet picture. What say we call it a night and let them sleep it off."
He pulled me into his arms and kissed me. He said softly, "I'm sure glad you and sis are working out. She needs someone as kinky as you."
As we kissed, I was feeling his growing cock in his shorts. I said in a whisper, "How about I get you ready for bed and put you to sleep?"
I stripped Dan quickly with clothes being tossed everywhere. When I had him on his bed on his back, I kissed him then went down on the monster meat. He was moaning instantly as I massaged his balls while trying to stuff his dick into my mouth.
Dan began stroking my dick within my jeans and soon had them loose and my dick free. I straddled his head and we began doing a number on each other, sucking, licking, nibbling. Soon we both were shooting loads and loads of creamy come into each other's mouths.
When we pulled off each other, we turned and kissed, swapping loads of cum into each other's mouths. Dan said, "Now I can go to sleep. I've had my snack." We kissed one last time before I left, pulling the locked door shut behind me.
As I was settling down to sleep after a quick shower, my room mate came into the room, stripped and climbed into his bed. Funny, but it almost smelled like perfume along with a sex smell radiating from him.
Jill, Mary, and I became a set. We were together for three meals every day, our workout, and spent a couple of hours each evening giving each other pleasure. When they had their monthlies, they would insist on giving me a blowjob which wasn't necessary.
Jake, Dan, and now Jimmy were still a fun group to play with in the evening and often on a Saturday or Sunday morning. The weather was getting nicer so ball practices were beginning. The football guys were doing spring practices. The softball girls were getting ready for the spring games and tournaments and the baseball team was getting ready for the spring season.
By the third week of practice, the coach had me at short all the time. The scholarship kid who had been at short was not a happy camper but the coach had the final say. I has hitting so good, I'm sure the coach would have used me in right field just to get my bat in the line up.
Jill, Mary, and I were spending every spare minute doing our homework assignments and preparing for class as we didn't have hardly any time after practice and a late supper. We would get to their room by eight thirty without enough time to even grope each other.
The guys upstairs were equally stressed and tired after three hours of rough, tough football practice. We all looked forward to Saturday mornings so we could get a little nasty along with get our clothes into the washing machines.
When it was time for spring break, I was planning on visiting home but found out we had a tournament in another city. The good news was that it was in my home town and the even better news was, there was a softball tournament there at the same time.
The school had made a deal with a hotel and both baseball and softball teams were staying in the same hotel. Jill, Mary, and I agreed we would have to careful as they would have personal bedchecks every night. We did work out a schedule between practices, meals, and games when we could get together in the mornings or afternoons for some fun.
I wanted Jill and Mary to meet my two older sisters. They were still living at home while attending a community college. I was the lucky kid as my dad figured I would probably get some form of a scholarship before my sophomore year. He was right too as the coach announced to me in front of my dad that he was putting me on scholarship for the next semester. He said I could go to summer school if I wanted for free too but he suggested I take a break then come back to practices refreshed.
Donna and Diane really liked Jill and Mary. The four of them had a great time together and visited for the entire eight days we were staying there. When Jill found out I played with my sisters, she was all over them, wanting them to stay over night with her and Mary. They did and Diane later told me that Jill had to be the wildest sex partner she had ever had. Donna thought it was sweet that I had two girls friends at school the same as I had at home.
By the time the spring tournament was over, it was time for practices for the season so I didn't have a chance to go anywhere other than baseball and a couple of meals at home.
What I did enjoy was getting back to my friends upstairs. The first thing I wanted was a mouthful of come. Instead of only a mouthful, I got two mouthfuls and three loads up my cleaned out asshole. They were as hungry for me as I was for them. We spent close to twenty-four hours from Friday afternoon to Saturday evening fucking and sucking. Jill and Mary had an out of town couple of games so I was totally available to play with the boys.
Jake had a new thing he liked to do. He wanted to be fucked and sucked at the same time he was giving a blowjob. He liked having three different guys on him at the same time. Jim was with us a lot and Dan brought a guy named Tom from his football team into our group. Tom was a big black guy that was afraid of his being gay. He had tried and tried to act straight, pissing off many girls because he wouldn't take a hint and go farther on a date. Dan and Jim showed him that he didn't have to be ashamed and that he only needed to act like any straight guy to get along.
Tom had a nice sized cock that seemed to never get a hundred percent hard. It was long and floppy. He could stuff it into a loose asshole but mostly he like to get head and be fucked. He did have a cute bubble butt that just begged to have a dick shoved up there.
Dan and I discovered he could get pretty hard if I was sucking him while Dan was pile driving his butt hole with his massive meat. The funny thing was that when Tom came, he just dribbled out of the head of his dick.
The foursome in Dan and Jake's room raised some eyebrows fairly often but when the guys would see me visiting, they thought it was cool as I had two girl friends on the softball team.
Each of us guys would take a turn being the center of attention. That was when we could suck a load from each of the guys, suck them back up and be pounded in the ass until they gave another load. Sometime one of the guys would have all of the others blast off on their faces. A real bukkake party.
Jake said that there was a gay group on campus that he wanted to get involved with. Dan said, "If you do that, then you better learn to use rubbers on them and us. Those guys are all loose and fuck around with townies and any other gay they can get their hands on."
Jake was kind of pissed because he felt as if we were holding him back. I dug out my Life Sciences Health book and had him read the chapters on sexual diseases to he would know what he was dealing with. Sadly, Jake didn't listen and announced he had attended a party orgy at a hotel downtown. He was trying to get some of us to fuck him but all of us said, "Go to the health clinic and get tested. If you're a hundred percent, we'll be balls deep in your mouth and ass in a second."
Jake wouldn't go until he got a spot on his dick. He went to the clinic and found out he had herpes and his HIV test came back undecided. He had to go back every month for six months to make sure.
The good news was that Jake decided Dan had been correct. The bad news was that Jake was so upset, he decided to quit school and go home. That was the end of Jake.
Jim made a room change and moved in with Dan. I had wanted to but Jim was a junior and I was the lowly freshman.
It was during this period that Dan and I had pooled some cash to rent a double at a local hotel so we could take our girls there for a night of wild sex. Dan brought Kathryn and Sandy and I brought Jill and Mary. This was a night of some firsts as while we were really getting it on. I was screwing everyone but Mary and Dan was porking Kathryn and Sandy. When he rolled off Sandy, Jill just happened to be next to her and he rolled right onto his sister. His huge dick slid into her gooey hole and he was pounding away. He knew it was her and she knew it was him but they were feeling really good about it. When he was blasting her insides with yet another load he said, "It's so nice to be fucking you sis. I just love the thought of you and I getting it on."
Later while the girls were all doing some mutual carpet munching, Dan and I lay down in a sixty-nine and pleasured each other with some good blowjobs. The girls thought that was hot and wanted us to fuck but we told them that it was too messy without the proper preparation. They made us promise we would be more prepared next time so they could watch us fuck.
Anyway, that was the night Mary wanted to lose her cherry. Jill and I tried to talk her out of it but she said she wanted to feel as good as Jill, Sandy, and Kathryn did when we were fucking them. Jill, Mary, and I went out for condoms and lube. When we came back, Jill and I spent a couple of hours making Mary into a mass of sexed up woman. Mary wanted to be on top and when she fit me into just the inside of her pussy, she slammed herself down on me groaning as she did. Within seconds she was coming while stroking me with her tight, hot, pussy.
She was so proud of her first fuck, she saved the condom in her purse vowing she would keep it forever. She also said she was going to get on some form of birth control so she could feel my juices squirting up into her.
Now that's the way to spend your freshman year at school.
Just before summer break, I came back to the room to drop off my backpack. When I came into the room, I didn't notice but roomie was in bed. Not only in bed but there was a girl in there with him. This was not good as if he were caught, he could be put on social probation. Girls were not allowed in the men's athletic dorm.
I was trying to be quiet when roomie looked over at me and smiled. The long haired girl with him raised her pretty face and smiled too. I said, "I'll be out of here in a second. Sorry to intrude."
My self righteous roommate said, "No problem Dean. I put you through enough shit before. Meet Andy, nice huh?"
Andy was on her back and pulled down the sheet to reveal a couple of very nice breasts. She cupped them as if to offer them to me and said, "You like these? Perhaps, Timmy would share me with you?"
Tim laughed but sat up with the sheet still on his lap but his dick holding up the sheet. Andy wiggled around and sat up showing dark stocking encased legs with a garter belt. When she sat up, the sheet was not covering her middle and she was not a she. She was definitely a he. A very well built, long thick he."
Tim said, "Guess you found me out. I like what Andy has. I like all of it. If you want, you can stay and play?"
I asked, "Are you a student Andy?"
He/she smiled and said, "Yes but when I come here, I'm dressed in the slacks and a shirt. I hide my tits so they don't show. One of these days I'm going to become a full time woman. Right now, I get to enjoy both worlds."
This was turning me on as I stood looking at them. Tim said, "Looks like you like what you see. Come over here and let Andy show you what she can do."
It took me less than a minute to lock the door and be completely bare. My dick was down Andy's throat faster than I undressed. She was sucking my generous dick and fondling my balls as I reached down and played with her tits. Roomie was trying to wiggle a tongue into the fray as Andy sucked me.
I told the two, "Lay back. Tim, get higher so I can get sucked by Andy and suck you at the same time." That was almost too much for him as he began leaking large drooling drops of precum before my mouth even had his dick in it.
Tim moaned, "Oh Dean, you suck so good. Damn, I'm going to come already."
As Tim shot into my mouth, I was squirting into Andy's. As soon as I felt like my last load had departed my dick, I switched around and buried
Andies cock into my mouth. It didn't take him but a minute to unload into my mouth. He moaned that this was too wild to believe.
Tim asked, "I thought you were hot with a couple of softball chicks?"
"I am Tim but that doesn't mean that I can't enjoy a mouthful of cum. I wish we could clean up a little as I'd love for you two to fuck me."
Again that was too much for Tim. He began shooting cum straight up in the air. Andy scrambled to get his/her mouth over him.
Tim said, "Damn, you would do that? Andy lets me do that but I haven't done it yet. Do you really like it?"
"I love to get my ass filled Tim. To bad we don't have a private bathroom or we would be fucking every night. Or at least you would be fucking every night."
Andy said, "I have to get my dick into your cute butt Dean. I'd love to have you on your back so I can watch you squirt while I slowly fuck your asshole."
Tim said, "Let's rent a hotel room. We can get one at the Marriott just off campus. I have the money, let's do it this weekend."
I said, "Perhaps we could invite a few others. I sure hope you two are careful and don't fuck around with townies. I shouldn't have fucked with you until I knew for sure."
Andy said, "I've been checked since I've been fooling with Tim. I took him with me so we would know we were clean. We were both a little overwhelmed with you just now though."
Tim said, "Do you know others who like this stuff?"
I smiled, "A couple but just enough for a real good fucking time. I also have a couple of girl friends that would want to come along. We could have a real party."
Andy said, "Oh man, I just love to watch girls get fucked. I want to see this. I can suck on their titties while you fuck them. Oh man, Tim, will you really buy a room?"
"It's a done deal Andy. My dad gives me more money than I can spend. I always have extra. Let's plan on this weekend."
That's how our first big orgy was organized. Dan with Kathryn and Sandy, Jill, Mary, and me, Jim, Tom, Tim and Andy all met on a Friday evening that none of us had any games or practices. We walked off campus and let Tim check into the Marriott. Soon the ten of us were up in the room. The girls used the bathroom first then us guys began cleaning ourselves out in anticipation of some heavy duty fucking.
The wild sight was Andy. He came into the room dressed like a guy with a long pony tail but in minutes he was one fine looking babe with bulgy tits, makeup and painted lips, nice hair, stocking with heels and a bustier. His really nice sized dick was sticking straight out to give the viewer that exciting sight of a transgender babe.
When us six guys were ready and came out of the bathroom, the girls were kneeling on the floor with their backs to each other in a circle. They were all excited by Andy and complimented him/her on her dress.
Jill said, "We want something special. We want your first load all over us. We'll help sucking you all but when you come, we want it all over us. Humor us okay? Come here, Dean, let me get that thing ready."
Andy wanted to be one of the girls but Katy said, "You have a dick and come in those balls. We get the first load then you can be as much of a girl as you want."
We ended up with the girls sucking and stroking our dicks in front of them. They ended up in a row in front of us and when we were all on the verge of shooting, Jill said, "Let'er rip." The four were stroking us, aiming us at their faces as the six of us began blasting shot and shot at them. Jill and Mary had their mouths open for my streams. I know Dan made an effort to get some in Jill's mouth as well as Kathyrn and Sandy's.
When the last streams dribbled out, the girls were gloriously covered in come. The fell on each other licking the come from each other's faces.
Tim got right into the game and was on his knees sucking Andy and Tom was sucking Jim. Dan and I paired up on one of the beds and were sucking each other until Jill and Kathryn came to claim us.
My second load was planted deep into Jill as we kissed lovingly. She said, "If you keep treating me like this, I think you should make us permanent. You and me are too much alike to be apart out in the big world. I think we can get Mary to come along and perhaps Kathryn and Dan. When we finish school we could have a house for ourselves and a continuous orgy."
My third load was demanded by Mary who had patiently assisted getting Jill off before. Mary loved the feeling of being filled and was planning on trying to stuff big Dan into her less used hole.
Soon Kathryn was on her hands and knees, inviting me to pump her plump pussy. While I was doing her, Dan got behind me and was lubing my butt hole. Jill came around and kissed me and said, "I'm gonna see my man fucked, fucked by my big brother and his huge dick. I'm coming without even touching myself."
Dan did fuck me while I fucked Kathryn. Soon Kathryn was filled with my juices and my butt was full of Dan's. My butt wasn't empty long as Andy wanted to get into me and was sliding her/his big one into me. Jill lay down in front of me so I could suck on her sloppy pussy. She told me that the extra juices were courtesy of Tom and Tim. She said they had both fucked her and lasted maybe thirty seconds each. When I had her cleaned out while Andy continued to fuck me, Jill slid up under me to get my hard again dick into her.
My ass was getting a workout at when Andy had deposited a load, Jim said he had to have some of my ass. He left a load while Jill was replaced by Sandy. After Jim finished, Tim sank his dick into me and again lasted about thirty seconds. I finished Sandy off with loads of cum dripping from my asshole.
My second to last fuck was Tom. He said he wanted me to feel how good his ass felt. It was good as he had a great bubble butt that really enjoyed having a dick shoved up there.
As we were all relaxing, after some showers, I was loving on Jill as Dan was next to me loving on Kathryn. Mary was on the other side of Jill and said, "You better fill her one more time. Next week is going to be lonely. We're both traveling and not to the same place this time. We leave tomorrow so you're going to be without us for a few days."
I said, "We leave Sunday and don't get back until Thursday. You guys have a tournament that starts Friday and will be leaving Thursday. Wow, we're going to really miss you guys."
Jill said, "Our only night together next week will be Wednesday. The other problem is that we all need to be studying for finals. The week we get back is all of our finals. I'll do a lot of studying while we're on the road. That will help."
We did make love, long and slow with some nice kisses and touches. I kissed her entire body spending some special time at her erroneous zones. By the time I was balls deep into her, she was coming continuously and this brought me to a mutual climax with her.
As we lay there, Jill said, "This place smells so good, we could just lay here and keep fucking for a week. Damn, I hate to have to go back today."
Everyone thanked Tim for buying the room for us. We actually straightened up the room so it didn't look too bad. Andy washed off his makeup and put his hair back in a pony tail. He said, "I'm glad it doesn't take me much to get dressed as Dan and Jim like to have Tim and me over often."
We walked back to campus where I kissed Jill goodbye as she had to pack and get to the bus to leave. I had a short practice then we were supposed to pack and meet at seven to get ready to ride in the bus all night.
That was the conclusion of my freshman year of school. Jill and Mary's home town wasn't that far from mine so we figured on getting together over the summer months. My dad had a job for me and Jill and Mary had summer jobs. That would take us through the summer.
At home for the summer, Donna and Diane were both going to summer school at the community college. Both would try to graduate a year early. While I was home, the boys introduced me to some variations they had discovered in their playtime but they mostly liked to suck. I was good with that but they were greedy and wanted all of juice for themselves. That wasn't nice.
A pleasant surprise was Andy. He was a resident in my city as well. He and I found ways to get together and take some rides so he could dress. He loved to ride along the highway with my dick in his mouth. He did supply me with loads and loads of creamy come that summer. When it was time to go back to school, Andy decided he was going to New York City to join the many transgender models that were up there. He had a job offer and was excited about going. Oh well, poor Tim.
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