The Misadventures of Calamity Callabyanastymouse©
Although Steve and John were dreamy hot, I survived the initial sexual tension with both, and the three of of us settled in as good friends. These were great guys. If I favored one over the other, well you know, it would have become complicated. We were pre med and spent many late nights studying at the library. I felt really spoiled as I always had two gorgeous male escorts to walk me back to my sorority. I didn't have any time for a new relationship and as the pressures of being an ivy- league freshmen increased, I became so horny I couldn't stand it. I began fantasizing about both guys to escape the tension. One night Steve. One night John. Steve was my left hand and John my right. Sorry Steve John is visiting tonight. It was great fun
My roommate Stephanie would spend weekends with her fiancé Jack. When she was at his place, I could be all alone with my thoughts. My best fantasy would start "Well guys why don't you both stay tonight"? I would fall into a dream world of two cocks; licking one sucking the other; both guys kissing my neck; messaging my tits, licking my ass; eating my pussy; and taking me at the same time. I played with myself for hours. How could I make this come true? I wonder who has the bigger cock? If one had a bigger cock would the other not want to go through with it? Go through with it it? What was I thinking?
I realized it was getting out of hand when I was caught masturbating. Steph had an early morning class and I usually would get up to shower after she left. I was up a little early that morning and after my shower I started rubbing baby oil on my boobs before getting dressed. It felt really good. I started by circling my thick areolas and pinching my nips. I thought I could jump back in bed and finish myself off before going to my 10:00 class. I started playing out what the guys would do to me and I lost track of time.....
"....You really need a guy," Steph smirked.
Ohh no she was back from class and I was so deep in trance I didn't even hear her come in. She caught me under my covers with "John" teasing my clit and "Steve" slowly massaging baby oil around my asshole.
I really need both my guys, I thought.
I had a habit of getting caught in embarrassing, strange and silly situations. You could say I was a little spacey. I forget where I park cars, and get on the wrong airplanes. I am always late for class. I loose cell phones into sewers, forget to wear panties, and work tirelessly on the wrong homework assignments. My name is Jen Callahan but the girls in my sorority call me Calamity Callahan.
I suppose spacey goes with being a horny little California blond with proud pair of 36Ds. I love my boobs. There were times during that first semester after spending most of the night studying with my guys that I would fall asleep holding my boobs as if I were feeding my tits to my imaginary lovers.
It was a real culture shock for me coming to New England. I am a California Manhattan beach girl. We take our bodies very seriously. The girls don't seem as interested in their looks on the east coast. I spend lots of money on clothes, hair makeup manicures, pedicures, the gym and because the sun doesn't shine in New England 5 months out of the year, I also send time in the tanning bed. I have long hair and a cute little bubble butt. I wish my legs were longer so sometimes I wear heels with shorts when I shouldn't to make my legs look longer and my ass look even tighter. I know I know not very ivy league preppie.
As for my guys they were a year older and had known each other since high school and were friends with Steph and her fiancée long before I came into the picture. The guys kind of adopted me as Steph's roommate. Very sweet. Steve was the taller of the two and more athletic. He had an on again off again relationship with this emotional wreck of a girl friend. John's body was not as nice but he was warm and gentle with beautiful blue eyes. He had a steady girl friend back home. Could I fuck John one night , and Steve the next without either finding out?
Stupid. Stupid Stupid. What a selfish little bitch. I had to stop.
I survived my first miserable New England winter and was very glad that spring had finally arrived. I had my jerking off under control. My grades weren't great but I managed not to wash out. Steph and Jack were getting married that summer and invited me and half the sorority up the Hamptons. My guys were going to be in the wedding and I was looking forward to seeing them in there tuxes. They brought their girl friends. I decided to go stag with a few of the girls from the sorority.
I booked this terrific room in a Bed and Breakfast with a massive poster bed and one of those old claw foot bath tubs, soft beige walls and lace curtains. Very nice.
Well as luck would have it the day of the wedding my rental car broke down and the other girls had already gone ahead to the church. I reached Steve on his cell and begged him to come back for me.
"Be ready when we get there Jen," he said with a serious tone.
"I will I will I need 10 minutes to get dressed tops." I had already showered but still probably needed at least another 30 minutes.
I had packed three pairs of shoes and was modeling each and couldn't decide which pair was best.
"Jen it's me are you ready." It was John. I swear they were back in less than 5 minutes
"No," I said sheepishly through the closed door.
"Jen open the door," he said with more than a slight irritation and resignation. I knew he wanted to assess how long it would take me to get dressed and report back to Steve.
I opened the door with my hair pinned up wearing a thigh high robe covering my bra and panties. I had not started my makeup. At least I had made a decision on the shoes and was wearing an adorable pair of gold metallics with four straps around my foot and a fifth around the top of my ankle. Great toe cleavage. Really cute.
John looked at me and didn't say a word. He sat down and called Steve on his cell: "30 minutes. Minimum."
"John I am so sorry."
"Jen the service is going to start in 90 minutes. It's 40 minutes back to the church. I am in the wedding. I need to be there early. What do you need to do?
I went through in every detail: moisturizer; dress; hair; makeup.
John sighed again and called Steve on his cell. You had better park the car and come up."
I suddenly had two guys staring at me wondering what to do next.
"Is there anything we can do to help," John blurted out. "Can you multi-task or something?"
"No, I only have two hands you know," I said while looking into the bedroom mirror applying eye shadow.
"What are you going to do next," Steve asked?
"I am going to baby oil my arms and legs. I don't want my skin to look dry"
Steve grabbed the bottle; kneeled and filled his hands and began applying it to my leg. I spread my legs a little more than shoulder length apart and did not say a word. I kept working intently on my face. John, not to be out done, grabbed the bottle and started on the other leg.
They passed the bottle back and forth and kept rubbing the outside and lower on the inside up to my knee.
Gradually they worked there way up my inner thighs and John chuckled a little and looked up at me in the mirror.
"Tell me how high you want me to go," he said.
"You are doing fine," I said, pretending not to know what was happening. My heart was pounding and I was trying to not to increase my breathing. I was already wet. I loved it. They loved it. They had lost track of time going over the same parts of my legs again and again working their way up a little higher each time. First , on the outside, and then slipping a little higher on the inside and smiling at the situation. Steve was almost massaging my ass cheek.
I pretended to absent mindedly take my robe off and throw it on the bed. Bra, panties, high heels. Perfect. I twisted my upper body slightly and bent over to John with my legs still spread apart. I let my boobs dangle in front of his face. I cupped my hands and said "give me some of that". John's mouth fell open. He poured some oil into my hands. I twisted up slowly not taking my eyes off him and began to rub my arms and neck and then the tops of my breasts. I then looked at Steve in the mirror.
I bent again and looked deep into John's eyes. "More please" I said, and cupped my hands. This time I massaged harder , and deeper into my breast cleavage. I couldn't hide my increased breathing anymore. My chest heaved up and down as a messaged the tops of my breasts.
Both guys were frozen on their knees looking up at me in the mirror. I took one deep breath and made time stand still. I looked at John and then Steve waited for a second, smiled at each in the mirror, reached behind my back and unhooked my bra and tossed it on the bed. I turned towards John so that my ass was in Steve's face. I bent over and slid my panties off so that Steve had a perfect view of my ass.
"Jen..." John said breathlessly. "We can't..you shouldn.."
I put a finger to his lips and whispered, "Shhh..its ok....enjoy this... enjoy me ... share me..and let me please you both....it's what I dream of all the time ..it's all right" And with that I stroked John's hair and offered my left tit to him as if he were a baby . I bent down a little further and gave him a reassuring kiss on his forehead. He closed his eyes opened his mouth and took my nipple. "Umm John," I whispered for him only to hear.
Steve had already begun caressing and kissing my ass. It felt wonderful. We all three had fallen into it like it was the most natural thing in the world. The guys were unbelievably giving and tender and I responded with soft encouraging moans. I arched my back to make more of myself available to both men. John was giving me soft sweetest kisses on my stomach while reaching up tenderly squeezing my boobs. He worked his tongue down to my shaved clit and then slowly back up licking and kissing until his mouth found its way back to my breasts. Both men flowed back and forth worshipping me with their hands and mouths.
Steve spread me open a little more and was teasing slowly around my asshole with his tongue. I twisted my ass up and down like a Brazilian dancer. I tried maneuver my bung hole so that he would stick his tongue in it. I kept missing and getting and more excited. I looked back at him and caught his eye.
"Ooooh..... Oh Ste... it's so goo.. your so.... good." He then twisted his head up under me so that he could get better access to my pussy. I spread my legs more.
To catch my breath, I rested my chin against John's head and let my hair fall over his face. I wanted to lean over and kiss him again but the sensations of both of them were unbelievable. My body stiffened and I began to shake. A wave came over me and my entire body convulsed. I couldn't offer myself anymore. I had to grab my knees to stand. John stood and grabbed my shoulders to help support me. I surrendered my mouth to his. He kissed me with more and more passion.
Steve was now more intently licking around my asshole and back to my pussy. Nothing had ever felt this good. I tried to roll my ass around again to encourage him. He grabbed my ass cheeks and plunged his tongue deep into my asshole. It was so unexpected and felt so good I couldn't keep kissing John. My head rocked back. "Ohh fuck yea...like that... lick my asshole like that...," I cried out and came again.
The next thing I could remember was John scooping me up and carrying me a few steps . He bent and let me gently spill into the big bed. I whimpered for them to join me. They were both still dressed with their pup tent erections showing through the pants of their tuxes. They had stopped to admire my body but the moment was lasting too long. I curled up on my knees and went over to each of them. I braced myself against the bed poster and kissed Steve first in appreciation of his tongue skills and then John. Each was standing on either side of the corner of the bed and I held on kissing John on one side and then Steve on the other. They did not resist my kisses but, I could feel them drifting back into reality.
They were thinking not acting. I slowly climbed back off the bed and got down on my knees.
I looked up at each and begged "I want your cocks, please let me have your cocks." I went after John first and struggled with his zipper. Steve popped himself out. His dick head was like a cute little red apple. I turned away from John and slowly slid Steve's cock into my mouth and gently cradled his balls with both hands like I was drinking wine from a large goblet.
I reached back as John had freed himself. . The guys let go again and we fell back into our rhythm. Slow and soft at first feeling their erections grow even harder in my mouth. I went from one to the other stoking and sucking. I gave a sweet little pop sound as a pulled away. They began to gasp and moan. I looked up as each stared down and I gave them the best eyes I had. We worked as a sex team. . Each man wishing to be pleasured but not wishing to deprive the other of the pleasure I could give. It was an absolute joy.
I started to moan creating more sensation on their dicks. John gasped. Ohh no, too much sucking for him.
I went back to Steve, easing my hand strokes with John hoping he was not ready to explode. I gobbled at Steve's balls, licked at the base and worked d all the way up to the tip of his dick. I licked up one side and then back down the other.
And then after a few moments back to John I barely touched him with my open mouth when....
" Ohh shit... Jen..I can't hold on anymore..."
"Give me those sweet juices," I purred.
He was cumming too soon and hunched over. I cupped his ass with both hands and wrapped my lips around his dickhead and held on. Steve was left alone to watch and jerk himself off. John exploded into the back of my throat. I drained him. Not a drop of his delicious jizz escaped. I swallowed his warm cum. It was wonderful. After a few seconds John looked down me with almost a sad resignation and embarrassment that he couldn't stop. I gave him one more long slow suck on his softening cock. If I had worked it I know I could have brought him back up. "It's ok baby..I'll be back for more later" I whispered.
Steve stumbled backwards slightly holding his dick ...the complete reality had hit him... his sweet little sorority girl sucking two dicks at the same time and joyously drinking cum shots. I looked up to him demurely. "Steve....please take my mouth now... I promise you ...you can have all of me later..." I pushed my chest out, grabbed the heels of my shoes, and walked on my knees over to him. I looked up at him like a baby bird begging for a thick juicy worm. I wanted him to put his dick back in my mouth without me grabbing it.
"Steve, ...it will be all right," John blurted out.
With a slightly pained look Steve guided his dick back into my mouth and then cradled my face in his hands. He looked down at me and begged, "Jen sweetheart... can you please finish me off quick too so that we can go to this damn wedding?"
I did and we made the wedding with plenty of time to spare.