Over Easter my boyfriend and I were both off work so we decided to drive to Chicago over the long four-day weekend. Unbeknownst to him I made contact with a bi-sexual man and woman via the internet, several months earlier. The trip to Chicago was my idea since they live there. I was not sure how he would react but he has always been pretty kinky so I thought he would be pretty receptive, even knowing that I kept it from him until now.
After we got off work Thursday evening we made the three-hour drive to Chicago so we would be there to begin our weekend on Friday morning. When we got to the hotel it was only ten o’clock in the evening so we opted to go out for a drink at a club. When we got to the club I excused myself to the restroom and called the other couple on my cell phone. They had seen a picture of me so I was not worried about them recognizing me when they arrived at the club. I reminded them that my boyfriend did not know about them so they were to act like we were just meeting them when they came up to us at the club. They confirmed and said they would be there soon.
I returned to my boyfriend who was sitting at the bar. He smiled when I approached him, “There you are. I missed you baby,” he spoke lovingly.
“Aww, I missed you too honey.” I smiled before speaking again, “It is so wonderful to get away for the weekend.”
He took a deep breath, “Yeah, it really is. I enjoy the fast pace of the city now and then.”
I saw his eyes on a cute waitress, and commented, “I think there are a few others things you enjoy about the city too.”
Shrugging and letting his eyes linger there a bit longer, he turned to me, “You would think I was dead if I did not look.”
Laughing, I agreed with him, “You are so right. I am glad you enjoy looking but I am even more happy that you enjoy having an open relationship with me.”
“Ah yes, well that works both ways,” he reminded me, “I enjoy allowing you to find a little strange on the side but I also enjoy fucking someone different once in a while too.”
I sat and thought a moment while he continued to check out the scenery. After being together for five years I know what he likes in a woman. I have noticed that some of the women he has chosen are more on the dominant side. My inner core is submissive but when he is in the right mood I am able to take on a more dominant role to please him.
One evening when we had too much to drink our conversation drifted to fantasies. A fantasy that he shared, after some hesitation, was the fact that he would like a Mistress to fuck him with a strap-on. At the time I was heavily intoxicated but his admission brought me to a state of awareness that trapped his confession in my mind forever. On occasion we have played with butt plugs. One time he took a rather large bulbous plug in his ass after a very long time of stretching and preparation. I remember when the plug finally slid in and his sphincter muscles slammed shut around it. He moaned deeply while he panted. Within a few minutes he was driving his cock into me hard and deep with the plug still buried in his ass. His climax was earth shattering because of the added anal stimulation.
I felt a shiver run over my skin, remembering that time while contemplating what this get-away weekend would produce, with the bi-sexual couple coming to meet us. He touched my arm, making me jump, “Are you ok? You seem a million miles away.”
Looking at him, I reassured him, “Yes I’m fine. I was just remembering a special time that we shared.”
“Mmmm, really? What time would that be?” he grinned.
Someone tapped me on the shoulder before I could answer. It was the woman I had talked to on the internet and her boyfriend. She did not let on that she knew me when she asked about the two barstools beside me, “Are these seats taken?”
“No, not as far as I know.” I answered her.
She extended her hand to me, “Hi my name is Anne. This is my boyfriend Peter.” She waved her other hand toward him.
I reciprocated, “Hello, my name is Jane. This is my boyfriend Richard.”
She chuckled, “How ironic, I have a peter and you have a dick.”
Richard could not help laugh at her comment, “Yeah, I was thinking that myself but glad you were the one to say it.”
I watched Richard as he took in the image of Anne. Her dark brunette hair cascaded over her shoulders. She stood at about six foot wearing black boots that came up to her knees. Black Capri pants settled at the top of her boots. A crisp white button-down shirt was gapping slightly to reveal a fair amount of cleavage… enough to wet any mans appetite.
Peter seemed to shadow her but was very handsome in his own right. I reached my hand to his, “Hello Peter.”
“Hello Jane,” he replied before stepping toward Richard to greet him. “He reached to shake Richards hand, “I don’t think I have ever seen the two of you here before.”
“Oh, we are from out of town,” Richard confessed.
“Really, what brings you to the city?” Peter asked to play along with the ploy and get to know Richard better.
Richard hesitated a moment while his eyes continued to drink in Anne then he turned toward Peter. “It was Jane’s idea, but I can already see that it was a great plan.”
We sat and talked for a while, primarily Anne and myself spoke while Richard and Peter talked alongside us. I told Anne that I knew Richard was attracted to her, which made her smile. When the band began playing a slow song I asked Richard if he would like to dance. We made our way to the dance floor. Peter and Anne followed and danced beside us. I knew why my back was toward them, almost the entire dance. Richard was looking at Anne. I let him look all he wanted, knowing that it would only aid the upcoming evening with them.
When the song finished they began another slow song to complete the set. Richard looked down at me, “Do you mind if I dance this one with Anne?”
“No honey, that’s fine. I will dance with Peter if you don’t mind.”
“That’s cool,” he spoke while smiling at me, “I think we may have some fun tonight.”
“Mmmmm,” I purred, before he passed me off to Peter.
Peter wrapped his arms around me and we began to sway. He whispered in my ear, “I think your Richard is smitten with my Anne.”
“Yes, it appears he is.” I reinforced his statement.
Peter looked down into my eyes, “And I am left with delicious little Jane, who I would love to ravish right here on the dance floor.”
I felt the heat rise in my cheeks. “Soon Peter, soon.” I reassured him with a wicked grin.
He leaned to whisper in my ear again, “Richard has a nice thick chest and narrow hips. I do hope he lets me fuck him tonight. Do you really think he will go that far?”
“I honestly don’t know Peter, but I do know that he enjoys anal play. My involvement with you and Anne is to find out if he may enjoy more. If not from you at least maybe he will let Anne use her strap-on with him.”
Peter licked his lips. “I hope he wants to go all the way because the thought of being the first cock in his virgin ass has my cock dripping with anticipation.”
“Are you gay, Peter?” I asked out of curiosity since he seemed so interested in Richard’s ass.
“No Jane, I am not gay. I am bi-sexual, which means I know no boundaries with regard to gender. All human beings turn me on, men and women alike. However, there are two things that make me melt, beautiful women and men with virgin asses.”
After what seemed like only a brief moment, the slow song was over. Peter escorted me back to our barstools while Richard and Anne walked back as well. Conveniently Anne excused herself and Peter for a moment, leaving Richard and I alone.
Richard took my hand, “Jane, are you game to have some fun tonight?”
“Yes, sure, what do you have going on in that deviant mind of yours?” I asked him with veiled excitement.
“When I was dancing with Anne I got so damn hot, I want her. I really think she is a domme playing coy.” He smirked. “How do you feel about Peter?”
“He seems likable enough. When we were dancing I felt his hard cock against my belly, so I think he is game too.” I reassured him.
He looked into my eyes, “If it is ok with you, I will invite them to our room, when they get back here.”
“It is fine with me honey. You know we will both enjoy this evening.” I smiled sincerely.
Anne and Peter returned a few minutes later, Richard stood and put his hand on Peter’s shoulder, “Would you and Anne like to join us back at our room?”
Peter feigned innocence, “What for?”
“Well, we can have a few drinks, talk and enjoy ourselves.” He said calmly.
Peter looked to Anne, “What do you think babe?”
Anne looked at Richard, then me. She stepped toward me and laid her hand on my upper thigh, “I think it sounds like a wonderful plan.” Her eyes drifted back to Richard, “Yes, it is an absolutely wonderful idea.”
“Very well then,” Peter said, “where are we headed?”
Richard took my hand, “Follow us.”
The four of us left the club and walked back to the hotel together. We stopped at a liquor store on the way and bought a bottle of wine to lighten our mood. Anne’s boots clicked on the paved sidewalk behind us, reminding me how good she looks in them. Richard had a silly grin on his face the entire time we walked, glancing at me occasionally to smile and squeeze my hand. One time he lowered his mouth to my ear while we walked, “I love you baby.”
I squeezed his hand in return and returned his smile, “Ditto.”
We arrived at the hotel and let ourselves into our room. Anne and Peter followed us, Peter commented, “Wow, you travel with class. This suite is spacious and nice.”
We sat at the dinette table in the room and drank a bottle of wine while we talked. Slowly our inhibitions faded even more. When the bottle was empty Anne grabbed it and laid it on the table, on its side. “Anyone for spin the bottle?”
Everyone laughed. Richard chimed in, “Why not, let’s do it. I haven’t played that in years.”
Typically when people play spin the bottle someone is shy and reserved but none of us were. When the bottle pointed at each of us we stripped off a piece of clothing with haste, anxious to continue the game. When Anne took off her blouse we were gifted to see her in a black leather corset, which took our breath away. Her breasts bobbled at the top, looking as though they would pop free at any moment.
When Richard took off his second piece of clothing it was his boxer shorts. An ample sized hard cock stood at attention, ready and willing to fulfill anyone’s dreams. We all proceeded to remove clothing until the only one with clothing remaining was Anne. She still donned her corset and black high-top boots. “I win!” Anne squealed with delight.
Richard looked at her, “I’m glad because as much as I would love to see you naked, the vision of you in that outfit is extremely intoxicating.”
Anne stood from her chair and walked to Richard, “Really? And why do you find my outfit so damn intoxicating?”
“It just is, I love seeing a strong confident woman.” He confessed.
Anne pressed him, “Why does that turn you on Richard?”
His wine laced, uninhibited voice said, “I have always wanted to experience being with a Mistress and you definitely look like one.”
“What a coincidence,” Anne said in a deep guttural tone.
“You’re a Mistress?” Richard asked in a slightly shocked voice.
Anne looked directly at him, “I am, ask Peter, he will tell you.”
Richard looked at Peter, “Is she really a Mistress?”
Peter walked to Anne and knelt in front of her, “She is my Mistress.”
Aghast, Richard spoke, “Well I’ll be a son-of-a-bitch. Of all the dumb luck.”
I spoke up, “It has nothing to do with luck honey. I hope you don’t mind that I arranged this for you, for us.”
“How? I mean, When?” Richard stammered.
“I will explain it all later, as long as I know you are ok with this.” I said apprehensively.
“OK? Hell, I’m fine. God baby, you are so good to me. This is fucking beautiful!” Richard grabbed me and kissed me hard.
Anne walked to Richard and told him to kneel in front of her. He let go of me and complied readily. She raised one booted foot to place it on a chair, exposing her pussy. “Lick my pussy,” she demanded.
Richard reached his mouth to her pussy and began lapping greedily. Anne grabbed his hair and pulled him closer. Peter came to me while Anne handled Richard. He lowered his hand to mine and helped me stand, then walked to the bed with me. We stood and kissed for a long while with our hands exploring one another. Finally I dropped to my knees in front of him and looked up. He fed his cock into my mouth, which I sucked hungrily.
Before long Richard crawled up beside me, at Anne’s instruction. “She wants me to suck his cock with you baby.” He said with some hesitation.
I looked at Richard with soft eyes, “Go ahead honey. It is a new experience, something to try. You are still my man, no matter what.”
Even though he was slightly apprehensive, he stretched his tongue to Peter’s cock. I continued to suck on the length of him while Richard dabbled with his tongue. Anne spoke firmly, “Quit playing around. Suck his cock like I told you.”
I withdrew Peter’s cock from my mouth so Richard could do as he was told. Slowly he took the head in his mouth and gagged slightly, “I don’t know if I can do this baby.”
Anne reinforced her demands. “If you don’t suck his cock this session ends with no ass play for you.”
Richard took hold of Peter’s cock again and began sucking, slowly at first until he didn’t gag anymore. Hearing Peter’s excitement drove him on, as well as hearing Anne’s comments about how well he was doing. Peter moved and crawled on the bed to lie on his back. Richard followed him and got on his hands and knees to continue sucking his cock.
Anne laid on the bed and spread her legs, telling me to eat her pussy. I delved into her bush with fervor. She had Richard and I trade places after a while, which pleased Richard greatly. Anne pulled out a blindfold and placed it over Richard’s eyes then had him stand. All three of us took turns sucking his cock, but he did know who was who. Even though he knew one was Peter it did not bother him, with the blindfold on.
Anne spoke to Richard, “I understand you enjoy having toys in your ass.”
“Yes, I do Mistress.” He said quietly.
“Good, I had Jane purchase a strap-on for this evening.”
I knew that was my cue to retrieve it from our bags, as well as the usual butt plugs we play with to stretch his ass at home. Anne spoke to me, “I want you to lube his ass and stretch it, like he likes it.”
I did as she instructed, while he crawled on the bed on his hands and knees. After applying lube I used the mid-sized plug and slid the tip in slowly, then further, watching his ass expand around it. After pumping his ass for a while I pushed it further until the widest part stretched him. Richard moaned and reached underneath to stroke his cock.
From behind me I heard Peter ask, “May I Mistress, please?”
“Yes Peter, you may.” She answered him then instructed Richard. “Peter is going to crawl underneath your upper body to suck your cock, do not forbid him.”
Richard stiffened when Peter wiggled under his body. I felt his ass tighten until Peter grabbed his cock and balls and began massaging him. His expert mouth milked his cock while he moaned with joy. Richard began to relax again so I reached for the larger butt plug. Anne stopped me and handed me the dildo that belonged on the strap on. I took it from her and lubed it then removed the mid-sized plug from his ass. When I tugged it out he let out a quiet moan.
Pressing firmly with the dildo his tight ass fought back until the head slipped in. He let out a soft scream, “What the hell is that?”
“It’s a dildo, but not much bigger than the butt plug we usually use.” I reassured him calmly.
“The fucking head is definitely bigger than the butt plug,” He panted, “Go slowly baby.”
“Yes honey, I will.” I held it steady for a moment then began to push again. It turned me on tremendously to watch his ass stretch to accept the dildo.
Anne instructed me, “Put your mouth on the end of the dildo and use your mouth to push it in his ass.” When I crawled behind him to use my mouth, it left my pussy and ass wide open for her. She grabbed the lube and the large butt plug and began working on me. Each time she pressed the plug into me, my body lurched forward, pushing the dildo further into his ass. We both screamed simultaneously.
When the dildo was buried in his ass she had me clench my teeth on it and pull it out slightly. When I back up she let the widest part of the plug slip into my ass. I screamed and panted, feeling my pussy quiver with need. My body reacted and lurched forward, shoving the dildo firmly into Richard’s ass. He screamed out at the same time.
Anne shooed me aside and fastened the harness on her hips. She told Peter to crawl out from under Richard and attend to my pussy. Anne removed the blindfold from Richard’s eyes and told him to look in the mirror before him. He saw the harness on her and knew she was going to connect it to the dildo in his ass. She did exactly that, as he watched.
Peter rolled me onto my back in front of Richard so he could see the butt plug in my ass while he used his fingers to pump my pussy. He had me turn my head and forced his engorged cock into my mouth, fucking it hard.
She popped the attachment into the dildo and began pulling the dildo from his ass, slowly, then pressed it back in. The look on his face was that of ecstasy and agony. Anne told Peter to fuck me while Richard watched. He slid his slick fingers from my pussy and pushed my leg further apart to gain access.
When he began to press his cock into me we both felt the resistance because of the big plug in my ass. Peter murmured, “Such a nice tight pussy you have Jane, god it feels wonderful. I can’t wait to stretch you wider with my cock.”
Although his cock was not huge, it was ample. He pressed harder until the length of him was buried, then let out a gut-wrenching cry, “Shit, your pussy is so fucking hot inside. If I’m not careful I will cum before the party is over.”
“Your cock feels wonderful. Fuck me now, fuck me hard.” I begged him. He started moving in and out, faster and faster until my body tensed and reached for climax. I begged and whimpered for him to fuck me harder. He bit his lip, “Fuck, your muscles are trying to milk me!” He pulled his cock out and held it with his hand, beating it against my clit, to keep from climax. Each time he hit my clit I felt the kaleidoscope return to my mind; I was entrenched in orgasmic bliss.
Anne grabbed hold of Richard’s hips and assisted him to move between my legs while Peter got out of the way. “Fuck her Richard, fuck her sweet pussy while I fuck your ass.”
Peter stood with Anne and spoke quietly to her then Anne spoke to both of us and continued reaming Richard’s ass with the strap-on. “Peter would like to fuck your ass when I am finished Richard, what do you think about that?”
Richard looked down at me with his cock buried in my pussy, “What should I do baby?”
“Honey, you should do whatever you feel like doing. You know I will love you no matter what.” I reassured him.
“But I don’t want you to think I’m gay if I like it.” He offered with a pained look on his face while she continued to pump away at his ass, patiently waiting for his answer.
I answered his query. “If you like it that doesn’t mean you are gay, if you still like my pussy. Peter explained to me that you might be bi-sexual, like him. He enjoys both men and women, but he is not gay.”
“I’m going to go for it baby.” He said as she drove the dildo deep into his ass causing him to thrust deep into my pussy. We both let out a moan and quit talking. Anne overheard our conversation and turned to Peter, telling him to lube his cock. Excitedly Peter dribbled lube all over his cock and stroked it to completely erection again.
Anne slid the dildo from his ass and left a gapping hole, ready for Peter, who readily stepping in behind Richard. He stood by the bedside behind Richard and lowered his cock to his ass. I looked up into his eyes when Peter grabbed his hips and spread his cheeks, aiming his cock at his ass. Richard’s eyes closed knowing what would happen in the next moment. Peter was kind and went slowly, savoring the virgin ass before him. He spoke to Richard, “Fuck her pussy good and hard so your ass relaxes for me.”
Richard drove his cock into me repeatedly, enjoying the tightness and wetness, emitting several moans and groans while he pummeled my stretched pussy. I felt my body reach climax again and screamed in ecstasy while he held still in my pussy like he usually does when I climax. In an instant I heard a sharp intake of air from Richard. Peter took advantage of the moment and drove his cock deep into his ass and held it there for a moment. Richard screamed out, “FUCK!”
He let Richard adjust before he began moving. We began a steady rhythm together, the three of us, with Richard in the middle of it all. The various expressions on his face reflected pain, pleasure and some expressions that I had never seen before. I knew he was enjoying this but it seemed as though he was experiencing sensory overload from fucking and being fucked at the same time.
Anne returned from the bathroom with the freshly washed strap-on. Taking aim on Peter’s ass she did not show him the mercy she showed Richard. Peter let out a high-pitched scream when she drove the dildo deep into his ass, then settled in and wiggled his ass for her to use. “That’s it Mistress, oh god you know just how I like it.” He cooed.
Richard looked into the mirror to view the chain of people behind him, fucking and being fucked. “Damn,” he said as he looked down at me, “This is so fucking hot baby!”
I responded, “Yes it is honey, it is SO hot. I, I, oh my god, I’m going to cum again!” I barely got the words out when a powerful orgasm coursed through my body, gripping his cock inside my velvet pussy. I came so hard I pushed the plug out of my ass and slipped over the edge into another earth shattering orgasm from feeling it slide out.
Richard drove into my pussy hard and fast, ready to take what was his. He pounded my pussy until his body trembled and he let out a deep belly moan. Letting loose inside me, his hot cum filled my pussy while his cock continued to throb and spew. He screamed out from the intensity.
Peter gripped his hips and swore, “Damn you, your ass is squeezing my cock, milking it… oh my god, I, I, oh shit!” He unloaded his cum into Richard’s ass giving Richard a new sensation. Now Richard knew how good it feels when he cums in my pussy. The three of us crumpled on the bed. Anne slithered her strap-on from Peter’s ass, removing it.
She crawled on the bed beside us and fingered her oozing pussy. After the three of us regained some composure we all turned our attentions to her. I licked her pussy while Peter and Richard sucked her tits that she pulled from inside her corset. She grabbed their semi-erect cocks in her hands and began sucking them alternately. Before long they were ready for more action.
She pressed Peter down on the bed and straddled his cock. Holding it up for her she positioned her body and dropped on him making him moan aloud. She ground down on him, driving him mad. She looked at Richard, “Fuck my ass. I want to feel two cocks in me. Jane you can spread those sweet little legs and straddle Peter’s face, so I can watch him suck the cum out of your pussy.”
Richard obliged her and lubed his cock to fuck her ass. She leaned forward slightly when he was ready so he could slide in her ass. A deep moan came from her body and she closed her eyes and bit her lip when he finally penetrated her, “Fuck yes! I love feeling my pussy and ass stretched!” She bellowed in a slow, deep haunty voice. “Fuck me hard men, fuck me HARD!”
They did as she asked and fucked her without mercy, driving, drilling and banging her harder than I have seen anyone fucked before. I straddled Peter’s face and squeezed my pussy muscles. Slowly cum began trickling from my body, which he lapped up greedily. He placed his mouth over my pussy and sucked hard, so hard that my pussy began to swell. It felt wonderful and engorged. I couldn’t help myself; I climaxed again and began to squirt on his face.
Anne grabbed my face and pulled my mouth to hers. We kissed deeply while I climaxed and moaned into her mouth. She kept kissing me until her body began to tense. She pulled away and held steady for a moment. I saw her eyes roll back in her head and her eyelids quivered dynamically before she screamed aloud, “Fuckkkkkkkkkkkkkkkkkkkkkkkkkkkk!” Not once, but five times before she finally collapsed on top of Peter, panting and sweating from the exertion.
In an effort to retain some of his manhood that he felt he may have been compromised, Richard spoke, “Take my cock bitch, take it up your ass,” while he continued to pound her puckered hole. One last thrust and he exploded inside her, drenching her bowels with his last drops of cum.
I slid off of Peter’s face while Richard slid out of her ass. Peter grabbed her slender waist and held her while he pounded rapidly up into her puffy, abused pussy. Just to see if I could get her to the edge again, I raised my hand and smacked her ass hard. She let out a shrill scream and kicked into gear riding Peter again. “That’s it, smack my ass, smack it hard!”
I continued to smack her ass until she climaxed again and continued to smack it all through her orgasm. Peter drove up into her from below. All we could hear was the sloppy wetness of her juices and their flesh slapping together. Peter screamed, pitifully, “Now Mistress, now please, may I cum pleaseeeeeeeeeeeee?” he begged.
She looked down at him with veiled eyes, “Yes Peter, now.”
He let out a deep wail when she finally gave him permission, bucking his hips wildly, whimpering as he shot his cum into her depths, “Thank you Mistress, oh god, thank you for taking my cum.”
The four of us showered and curled up in the huge king sized bed for the night. Anne was finally free of her corset and boots, revealing a gorgeous body which Peter and I curled up next to on each side. Richard lay behind me, spoon fashion, snuggling into the fray. He whispered in my ear before we drifted off, “I love you baby.”
I turned to him for a kiss, “I love you honey.”