Naughty Gift Exchange

I am obsessed with Madison, my amazing catch of a girlfriend. Not only is she a beautiful strawberry blonde with a bright smile that always gets me, she had delivered on an incredible fantasy for my birthday. Now, I knew I had to get her something just as special for hers. The most obvious thing for me to get her was to fulfill a fantasy of hers but when I asked her she demurred, "no, I don't think I really have a fantasy."

I suggested other gifts like jewelry ("I don't really wear much"), until I got frustrated with all the dead ends.

The day after Madison's naughty gift was my actual birthday. We both took the day off and Madison came over to my place. She looked amazing and soon we were naked and in bed, with her on top of me.

"Is this the way Monica sat on your face?" She asked sweetly as she looked down at me, her pussy inches from my mouth. I had tried not to give too many details but knew she knew the answer.

"No...she...uhhh...faced the other way..."

"Really?" she asked in an innocent voice. "Her ass must have been like...right in your face!"

I blushed as my cock twitched. "Like this?" Madison asked as she turned around, her ass brushing my nose before hovering tantalizingly close.

"Yes...mmm...like that."

She pushed back so my nose was in her ass crack. "But her ass is HUGE...your face must have been right in it!"

My response was muffled as I spoke into her ass, "Yes...it was."

"Wow." she giggled. "Did you...beg to tongue her asshole?"

It was clear she had discussed specifics with Monica but I was still shy to talk about it. "I...."

Madison bounced up and down, so her ass crack ran along my face. "Stick it out and show me what you got!" she taunted. I had never seen Madison quite so...aggressive.

I stuck out my tongue and she pushed back all the way so I went deep into her tiny asshole. She moaned a little and I tongued her, trying hard to make her happy.

"Ohhhh....I bet she liked that!" Madison said, mockingly. "You were her little ass bitch."

I felt a strange mix of shame and arousal, but said nothing, continuing to tongue her ass. Madison pulled away suddenly and looked over her shoulder at me, "Weren't you?" she demanded.

"Yes." I said. It gave me an intense thrill to see her take charge like this, exposing my secrets and wielding them against me. Madison looked down at me with a playful smile and I added, "I was...her little ass bitch."

Madison suddenly turned around and straddled my chest, looking down at me, "But whose submissive bitch are you every day?" she asked.

"Your bitch." I said enthusiastically.

Madison gave me a shock with a slap on my face, "That's right...and you love pleasing me don't you?" she asked, smiling down at me.

"I do...I really do...thank you."

She laughed then put me inside her then bucked as she played weith her clit until she came. Afterwards she lay with her head on my chest. I told her it was hot to see her take charge like that and she said it was fun to see me be so submissive.

After quietly enjoying this postcoital cuddle a while my mind kept going back to Madison's comment last night that she was excited to see what I would get her for her birthday. She had said it in jest but of course I wanted to get her something special.

"Is there...a fantasy you have that we can fulfill for your birthday?" I asked a little tentatively.

She was quiet for a moment as if thinking, then answered, "No...I'm happy with my submissive bitch", and kissed me on my neck.

I smiled and kissed her lips. "I could get you some nice jewelry?" Madison's nose wrinkled, "Nah...I don't like to wear a lot."

This was true but now I was worried I wouldn't have anything special for her. I felt a knot in my stomach just from the idea of disappointing her on her special day.

"You're sure you don't have any fantasies?."

She smiled a little then looked away, "No...not really" she said.

"Come on..." I said, tickling her side, "there must be something."

"Well..."

"Go on...you can tell me."

"Well...it's...sometimes I imagine what it would be like...you know...to be fucked by a really big cock." she burst out in nervous laughter, very different than the girl who was so aggressive with me minutes earlier.

I was a little shocked, and of course thought of my own, rather average sized member. "You...must have had bigger cocks than mine?" I said tentatively.

Madison quickly reassured, "Oh no...yours is fine baby", she paused as if choosing her words, "I mean of course I've had my share of different cocks...it's just...I wonder what it would be like to be really filled up."

I got a little nervous at the idea, "Sure...I get that. But where would we find someone that big?"

"Oh...I mean it's just a fantasy." she said, burying her face in my chest.

"Yeah....I mean I guess there's no way of knowing who..." I said, not finishing the thought.

"Well...", Madison said quietly.

"Huh?"

"Well, there is a guy. But...I mean maybe just a bracelet like you said."

"No." I said my throat dry. "You...know a guy with a...errr..."

Madison shyly kept her head looking down at my chest. "Do you know Jack from the 12th floor?"

My heart pounded in my chest and I wondered if she could hear it. I knew Jack. I had heard him talk about the many girls he had fucked, and (not knowing I was her boyfriend) how he intended to get to Madison one day. I had even jacked off imagining him taking her, something I had never imagined with any other guy.

"Yeahhh...I do", I said quietly.

"Oh...no, it's silly." Madison said shyly.

"No...why...do you think...?'

"Well", she started, "Monica went out with him a couple of times and...she said he had a monster dick."

"Oh...ummm...lucky him." I said as I collected my thoughts. "But how would I..."?

"I'm just being silly."

"No...I mean, it's your birthday, and...you made mine very...special."

"Well...maybe you could...ask him for me? Tell him I want his big hard cock?" I didn't answer immediately, and I felt her small soft hand wrap around my cock. "Wouldn't my submissive bitch love to do that for me?' she cooed.

I hardened immediately and she giggled, "See...you love the idea", she lifted her head and looked me in the eyes, "You could walk up to him and say, my girlfriend asked me to see if you would fuck her with your big cock." Monica was smiling but looking at me earnestly as she slowly stroked my cock.

"I'm sure he would." I said, wondering if I could really go through with it. "And then you'd..."

"And then he'd fuck me", she said matter of factly. "He'd push inside me and fill me up." She looked at my hard cock and softened her tone, "Would that be ok? Maybe you could watch since we are 'exclusive'?"

I wasn't sure if she meant that last part, but I imagined what it would be like to see big Jack on top of my girlfriend and she offered herself to him desperately. Madison started to stroke faster. "Or maybe that's too much, even for my birthday? Having my boyfriend arrange a date for me, then watch while I get fucked hard by a giant cock?"

I started to shoot and Madison giggled as she milked me completely, then kissed me on the cheek when I was finished. "Oh yay, this is going to be the best birthday ever!"

Madison's birthday was still weeks away, so I had some time before taking on this humiliating task. Madison didn't pressure me about having the discussion, but she did bring his name up every time we had sex so I knew she hadn't changed her mind. She would sit on my face and tell me how good my tongue felt, then say how amazing it would be to have Jack's big cock push inside her.

The threat/promise of Jack made having sex with Madison even more exciting and truth be told I was fantasizing about it even when I jacked off alone. But when I imagined actually approaching Jack about this I wasn't sure I could do it. On Thursday, with her birthday coming up that weekend, Madison finally asked me if I really was going to arrange this. I told her I wanted to but I was having a hard time actually doing it. Madison nodded with understanding but then dropped the bomb, "Of course. It won't be easy for you, even though I know you are desperate to please me and excited to make it real. Let me text Monica and she can coach you through it. She knows Jack and is good at things like this."

I wasn't sure what 'things like this' might include but I got very nervous imagining talking to Monica about it. Truth be told I had avoided Monica at the office since the night she had pushed her giant ass in my face. I was shy to look her in the eye after she made me beg to lick her asshole and I showed her my submissive side. In fact I had avoided all the girls in the office, unsure of how much they might know. But now was the time to be a man and make sure my girlfriend had a great birthday. I approached Monica at her desk the Friday morning as she and Madison had agreed. Monica looked amazing in a low cut red dress.

"Hi Puppy." Monica said cheerfully, making my face turn red.

"Hi Monica...ummm...can we go get a coffee so I can..."

"Awww...sure, I guess we can do that."

We went down to the lobby coffee shop and as I brought Monica her coffee order she said brightly, "So I hear you are planning a special birthday for Madison!"

Even though the others around us had no way of knowing what this was, I felt very embarrassed. "Yes, I want to...I mean...I am just a little..."

Monica surprised me by putting a finger on my mouth, then cupping my chin in her hand, "You need to make this happen. Madison got you something very special for your birthday, now you need to man up and ask Jack to give her what she wants." I nodded, a little stunned and rather aroused as Monica looked me in the eyes and smirked, "And believe me puppy, she's gonna LOVE it."

Monica helped me make a plan and offered to help. We set forth to Jack's office but with every step I took my legs felt more wobbly and my throat got drier. Be a man. Make her happy. This is what she wants. You are her submissive bitch. The mantras pounded in my head, warring with the sheer, crushing weight of my pending humiliation. How could I articulate this? How could I ask another man to take my girlfriend, a woman I adored?

When we arrived my heart was beating really fast and I felt hot. It was Monica who knocked. "Hey hon", he said, clearly surprised to see her.

"Hey Jack", Monica said, suddenly seeming a little shy. "Hey, I think you know Caleb?", she said, nodding towards me.

"Oh, yeah, we've met, right?" Jack said, still sitting and looking confused. He was even taller and bigger than I remembered.

Yeah...I mean, we had lunch with Benjamin."

"Ah, yes." he said, still seeming unsure.

Monica looked at me anxiously and I began, "Well...you know Madison on our floor?". Jack nodded curtly, wondering why we were there. "Well...I'm her...boyfriend and it's her birthday and...she wanted you..." I spoke fast then choked before I finished.

"Tell him Caleb", Monica demanded.

My face burning red, I barely managed to say, "she asked if you could...fuck her?"

"Fuck her?" Jack said loud enough that I worried the girl in the cubicle outside his office could hear.

I nodded, unable to find my voice as I found myself shrinking, wishing I could disappear into the floor. He looked at Monica and she nodded with a smile.

"Yeah...I could do that." he said, chuckling. He thought for a moment and licked his lips, "And what would you be doing while I took care of her?"

The humiliation was too great to speak, and it didn't help that an erection had formed in my pants as I imagined big Jack 'taking care' of my sweet Madison. Monica jumped in, "Oh, he'll just be watching." she said with a sadistic smile. I tried to nod. I hadn't discussed that with Monica but apparently Madison had.

"You want to watch me fuck your girl?", Jack asked, loud enough that I was sure the girl outside his office could hear. I nodded, wanting to melt into the floor.

"And I want pictures!" Monica chimes in cheerfully. "One of you boys make that happen."

I texted Madison to tell her Jack would be coming over the following night and she thanked me and told me how excited she was for her gift. That night as we fucked she kept reminding me that Jack would be enjoying her tomorrow. "Imagine how deep he'll go if he gets me on all fours like this?" "Do you think he'll like my pussy more than Monica's?" "Mmmm...that's it baby, warm me up for Jack tomorrow.".

I came too quickly but Madison reassured me that it was good to get some rest before the big night. She fell asleep soon and my cock got hard again imagining Jack fucking her while I watched.

On Saturday neither Madison nor I could seem to think about anything else than the pending evening activities. She giggled when we woke up that I would have to give up my bed to Jack later, but it was clear she was as anxious as I was. And yet I was in a constant state of arousal, barely believing that this was really going to happen.

"You'll be a good boy and let me enjoy my gift won't you?" she asked as we smoked a little weed that afternoon.

I promised her I would be. "Good." she said. "Mmmm...I have a feeling you might enjoy it almost as much as I do." she teased as she pushed her bare foot into my lap and poked at my growing arousal. I went to kiss her neck but she giggled and pushed me away, "Now now...why don't you help me pick out an outfit for Jack?"

We chose a simple short plaid skirt with a white shirt, no bra and pink panties. With her strawberry blonde hair, creamy white skin and freckles, she looked like an innocent girl who was heading out to a club in a slutty outfit. But we weren't just waiting for her gift to arrive.

When I answered the door I saw Jack looking like a mountain of a man in a black t shirt and black pants. I had only seen him in a suit and tie at the office but the size of his arms now made it clear that he was a gym bro who lifted. As I promised Madison, I thanked him for agreeing to be my gift to her.

"No worries Craig, where is the birthday girl?"

"Oh, my name is Caleb, and...she's right in here." I said, showing him to the main room. Madison was standing there with a nervous smile and Jack looked her up and down.

"There she is", he said in his deep voice. "Nice, you look hot." he said. "Give me a turn". Madison giggled and turned for him. "Very nice. Come her babe" he instructed. Madison obediently went to him and fell into his big arms, pressing against his body. "Oh we're going to have a good time", he said.

Madison giggled again. To my surprise her hand went down to his pants and she stroked the outline of what was already evidently a large cock. "Can't wait to unwrap your gift?" Jack laughed. A sharp pang of jealousy pierced through the heat building in my groin. This was my girlfriend, stroking his cock with an eagerness I hadn't seen directed at my own in that specific way. Yet, even as the humiliation threatened to consume me, my less impressive cock throbbed, a shameful testament to the perverse arousal that was inextricably linked to this scene. It was a bizarre, internal war, fought within the confines of my own skin.

Jack seemed to revel in Madison's eagerness. He reached under my girlfriend's skirt to give her ass cheek a spank, "Why don't you pull it out and take a look?"

Madison looked over at me as if to get permission and I found myself nodding to reassure her. Madison got on her knees and unzipped his pants and quickly pulled out his already erect cock. I heard her gasp. The rumors were clearly true, it was large in girth, and especially length where it was more than both Madison's hands. "It's...beautiful", she said, stroking it lightly.

"Don't worry, I'll make sure you can take it all", Jack assured her. "Why don't you take me to the bedroom and strip out of that little outfit."

Things moved very quickly after Madison took Jack by the hand and led him to my bed. I took a seat beside the bed and watched as Madison stripped down quickly, first pulling off her short and exposing her small, pert tits and pink nipples, then pulling down her skirt and panties at the same time so she was presenting herself completely nude to him. Jack removed his shirt, showing off his big chest and abs, then pulled down his pants as he lay on top of her, sucking on one tit. Cock aside, he was twice her size and it was striking to see his big body on top of her.

"You sure you're ready?" he teased as he pushed two fingers inside her already wet pussy.

"Yes! Yes please Jack, I want you to fill me up!" my girlfriend pleaded.

Jack laughed and told her not to worry, she was going to get the gift she had been begging for. He put on a condom and told her he was going to push in slowly so she could handle it. I watched as my girl spread her legs for him and saw him put just the tip inside her. She moaned loudly in excitement and anticipation. I stroked my cock through my pants.

"More Jack, please!" Madison begged. Jack immediately pushed much further into her and this time Madison let out a yelp and moan of pain mixed with pleasure. "Oh god, that feels so good." she cried.

Jack started to push in and out of her but warned, "Oh, here is still more to go, are you sure you're ready?"

Madison seemed a little surprised, but was eager, "Yes...ok yes...fill me up all the way Jack."

This time he waited, pumping faster and faster as I watched and heard the sound of her juices. Finally he gave a strong thrust and he was all the way inside.

"Mmmmmmmphh.....uhhhhh.....oh god you're huuuuge!" Madison cried. "Oh you're so deep." Jack started to pump even harder, shaking my bed and seeming like he might go through her.

"You like that?" Jack teased. Is my birthday slut enjoying her gift as her cuck boyfriend watches?

Madison assured him she was loving it. I was startled to hear him mention me, but took the cue to pull my cock out and start to stroke and he continued to destroy my girl. I watched Madison cum loudly. I had made her cum before but never that fast and never by fucking her. Jack didn't let up, driving his big cock in and out of my girl without mercy. Madison kept her eyes mostly closed as she loudly continued to moan, but for a moment she looked over at me and mouthed 'thank you'. Something about that intimacy drove me over the edge and I started to shoot cum while Jack continued to fuck her. Madison came a second time and soon after he flipped her over and entered her again from behind. Wincing in pain but clearly loving it, she told him he was even deeper now, "I've had many cocks inside me, but never one this deep!" she exclaimed.

Jack was holding on to her hips, allowing him to slap hard against her ass without knocking her into the wall. Madison pushed her head into a pillow muffling her moans as she kept her ass raised for him. Finally he came, pulling her body into him for his last thrusts.

Madison lay there exhausted for some time as Jack pulled off his condom and took a break. Then, for a moment, she was mine again, motioning for me to come closer then stroking my face and thanking me for the 'best birthday' as she lay spent, face down on the bed. The smell of sex filled my small room.

Suddenly Jack smacked her ass hard. "Oh it's not over yet" he announced. I came all the way over here and I'm going to have to pop twice." He paused a moment and smiled, 'besides, I hear you are an amazing cock sucker."

My mind raced, wondering who had told him this. Madison had kissed and licked my cock, but she had actually never given me a bj. I actually loved kissing her body and going down on her so much I had never missed it, but it was still a bit shocking to hear this was a special skill she had.

Madison smiled, pretty clearly game to show him, but wanted to make sure I was on board. "Oh baby, is that ok?" I didn't answer right away, and she added, "Oh, I can sit on your face and you can try to make me cum again while I try to take his giant cock down my throat!"