Free Erotic Stories

Office Assistant - Part 4

It’s been about a month since she started working with him. She was making progress on getting his office affairs in order. He was very pleased with her work and everyday he his feelings for her were becoming deeper. He loved her naughty side yet loved her sensual side too. The idea of making her fantasy a reality was all that he could think of. He loved his encounter with the couple long ago and had always wanted to try it again. Pleasuring a woman in that manner stimulated him and he wanted to experience this with her. He begins making plans for her fantasy.

Reaching out to his friend from college, he was certain that he would be on board, he had just gone through a terrible divorce. In one of their conversations, his friend had expressed how much he missed being intimate with a woman. Their conversation started like it always does, each sharing with one another what’s happening in their life. Chris then brings up why he called. His friend listening attentively to every word.

“So just so I understand, you have a new assistant who you’re falling in love with, and you want me to help you with her fantasy to be with two men. Are you sure you want to do this?” He asks.

Chris shares his experience from long ago and shared how hot and erotic it is, you’ll see if you agree. This will be a surprise for her, and I promise you, she’s, an amazing lover. We can’t get enough of one another; we have sex at least 5 -6 times daily. Some days it’s difficult to get any work done, laughing.

“Okay, I am on board. So, when do you want to surprise her? I could fly out this weekend if you would like.” He says.

“Man, that would be perfect. Can you be here on Friday? I will pick you up and we will get her fantasy weekend started. Are you sure you’re up for this?” Chris asks.

“Yeah, of course. You know it’s been a long time and I’d do anything for you man.” Joe says.

“Great, you won’t be disappointed. She’s beautiful, sexy, and smoking hot in bed, this is part of what I love about her. How this came up is we went toy shopping, she wears a butt plug daily, it’s so erotic. Anyway, we bought a toy that allows me to DP her. She loves it. I told her that she would love the real thing more. She trusts me and agrees to allowing me to surprise her.” Chris shares

“Wow man a butt plug? The visual in my head, thanks man. I am looking forward to meeting her.” Joe says.

“Okay, I’ll see you this weekend. Send me your itinerary, looking forward to this.” Chris says.

He’s already busy in his office when she arrives. He greets her with a tight hug and kiss and expresses how much he missed her the night before. “Before we get started today there’s been a change in our schedule this week. I have booked you a spa day on Friday while I play golf with my buddies. We will meet back here after and will go out for a nice dinner. How does that sound to you?” He asks.

“Thank you, that sounds marvelous.” She says.

“Great, I have a couple of meetings shortly, let’s see if you observed the dress code. Bend over, he commands.

Lifting her skirt rubbing her ass, gently spanking one cheek and the other says

“Good girl, you’re dressed perfectly. Let’s meet after my meetings to review the rest of the day.” He says.

Leaving his office, she was a little disappointed that he didn’t initiate morning sex with her, it made her wonder. She was falling for him deeply and craved their sexual encounters. Knowing she had a lot to do, she concentrated on her work. A couple of hours had passed, she wondered if he was still in his meetings. She peeks in his office tapping on the door gently. Looking away from his work he says,

“Come in, I just finished up, your timing is perfect, and I do believe it’s time for our lunchtime inspection. Come her beautiful and sit in front of me”. Sitting on his desk facing him, her legs together she smiles at him,

“I hope your meetings went well. I purposely didn’t interrupt you today. I wanted you to stay focused hoping that maybe we could take the afternoon off. I have finished my duties for today.”

“Well beautiful, taking the afternoon off is an option however will depend on your mid-day examination. Spread your legs for me.” He orders. Spreading her legs wide, he massages her clit. “Good girl, you’re soaking wet, fingerbanging her while massaging her g-spot, moaning she whimpers, “You’re going to make me cum.”

“Squirt for me beautiful.” Pushing his fingers into her harder and harder

“YES, ah, ah! She screams, I am cumming”, squirting her juices on his fingers.

Removing his fingers, he shoves his cock deep inside of her. Grabbing onto her hips, pushing harder and harder, he whispers

“I am going to fuck you so hard today you naughty girl.”

She responds, “promise?”

And just when she thought he couldn’t possibly go deeper, one thrust pushed her back.

“I promise.” He moans.

Holding onto one another catching their breath, he says.

“I don’t want to sound like a broken record, but this gets better and better every time. I love how we respond to one another, it’s incredible.”

“I agree, it’s like you unleashed something in me or we unleashed something in one another.” She says.

Agreeing to end the workday, they make some lunch and discuss the rest of the week. He shares that he has a couple of out of office meetings giving her the opportunity to either work from home or at his office. Friday will be an off day; you have a spa day, and I will be playing golf he adds.

We will end the week with a romantic dinner out.

Friday has arrived, she has no idea what he has planned for her. He’s nervous yet excited for the weekend. He sends a morning message to her,

“Enjoy your spa day beautiful, I will see you this afternoon.” Responding,

“Thank you handsome, I can’t wait for our evening, please enjoy your day.”

He has already shopped for her and prepared everything for her fantasy. He’s hopeful that it will be everything she imagined.

Arriving at the spa, she was surprised at the services he had booked for her. The attendant informs her of her treatments which includes a 90-minute massage, a facial, a makeup and hair session. She’s informed that her massage will be performed by two massage therapists due to the length of the massage. Having had massages before she was curious why there would be two, her mind wondered. She’s lead to the massage room; the attendant tells her the therapists will be with her shortly.

Joe, the masseuse enters the room. He asks her if there are any areas that need attention or that are off limits.

“Off limits?” She asks.

He tells her that they offer to a select few clients the option to have their bum and / or breasts massaged, asking her if this would be of interest to her. She’s never heard of this however she liked the idea. She agrees. He leaves the room allowing her to unclothe.

Starting at her neck to relax her. Down her back she feels two sets of hands massaging her. Massaging her legs, taking their time, one moves to her ass and then the other. Parting her ass cheeks, dripping oil in her crack, the masseuse’s each place a finger on her sweet spot, gently rimming her. Wondering what’s happening yet aroused, her ass rises as an invitation.

“How does that feel.” He asks,

“It feels wonderful.” She says.

Massaging the entrance to her anus, feeling one finger and then another enter her anus. Moving their fingers in and out slow and gently, she loves the sensation and feels a climax coming on. The masseuse’s take their time fingerbanging her ass. She moans and she whispers,

“This is going to make me cum,”

Keeping a steady pace, they fingerbang her ass until she climaxes. Removing their fingers, massaging her ass cheeks, gently spanking her. Moving their hands up her back, he instructs her to turn over onto her back,

“Please keep your eyes closed.” Joe says.

Starting at her feet, massaging her tone legs, their hands open her legs slightly. She feels their hands brush across her pelvic bone. Up her stomach, to her breasts. Massaging her breasts, each pinch her nipples gently at first. Asking her how it feels, she responds,

“Amazing, a little harder please.”

They respond to her request twisting her nipples between their fingers. Her body rising, moaning,

“That feels incredible, would it be too much to ask you to please suck my nipples?” She asks.

Cupping her breasts, licking, and sucking her nipples gently at first waiting for her response.

“Suck harder.” She requests.

She has no idea how much time was left; all she knows is she the feeling of two men massing her body felt amazing. She thought about her fantasy and hoped that Chris would surprise her soon. The therapist tells her there is another option for select clients if she is interested. Asking what that was, he tells her,

“We offer Yoni Massages, are you familiar with that?” She is and responds, “Yes, I know what that is.”

“Is that something that interests you today? We have another 30 minutes.” He says,

“Yes, I would like to experience that.” She whispers,

Moving their hands slowly down her belly to the top of her pelvic bone. Feeling their finger’s part her pussy, slowly massage her clit. She feels one and then two fingers enter her pussy while two fingers massage her clit. Slow and gently, their fingers move in and out of her pussy massaging her g-spot. Slowly moving her hips, she moans

“This feels incredible.”

They continue massaging her slow and gently for about 20 minutes. Wanting them to finger fuck her harder and faster, she whispers, “Harder and faster please.”

They accommodate to her request, both pushing their fingers harder and faster deep inside her pussy. Fingerbanging her harder, her hips thrust up and down, her body shakes, she feels a climax coming.

“Ah, ah, yes, I am cumming.” Squirting her juices soak their fingers.

“How do you feel?” Joe asks.

“Amazing, I’ve never had a massage like this before. I think I should return for regular sessions. She says.

“I am happy that you enjoyed your session. If you would like to schedule another session, you can request me and Phillip. We are new here and happy to accommodate anything you desire.” He says .

“My lover booked this for me. I wonder if he had anything to do with this.” She says.

“What do you mean? Do you think he knows about the special services that Phillip and I offer?” He asks.

“Well, that’s a good point I suppose he likely doesn’t. I am sure that he will want to know how it was. I guess I will leave out the special treatment.” She says.

“Do you think he will be upset? I mean you just had two men worship your body. Do you think he would be jealous? He asks.

“No, I don’t think he would be jealous in fact he would likely want to watch or join in. You see I have a fantasy of being with two men and he wants to make it a reality. After my massage I want it even more!” She says.

“Well, if your lover wanted to join in on your next session that could be arranged. Be sure that you book a 120-minute massage, with 3 of us we will need more time to service your needs.” He says.

“I will keep that in mind and will let him know.” She says.

She dresses and goes to her next appointment. The stylist asks how her massage was, she responds with incredible. Arriving at his home, he asks her how her spa day was. Hesitant to share her massage experience with him she responds,

“It was amazing, thank you so much. I loved my massage and I think we should do a couples massage someday.”

“I like that idea” Smiling back at her.

“I hope you don’t mind, there’s a small change in our plans this evening. I took the liberty of ordering a gourmet meal for us, rather than going out we can have a lovely dinner at home. I know you wanted to wear your little black dress and you still can. Is this okay with you?” He asks.

“Sure, I don’t mind. It will be lovely and yes; I would still like to dress up for you if that’s okay?” She asks.

“Of course, darling. Come with me, I have a surprise for you.” Taking her hand, he leads her to the bedroom. Laid out on the bed is sexy lingerie, a cup less bra, crotchless panties, her butt plug, and strappy high heeled sandals.

“I would love if you would wear this to dinner, no dress just this. Would that be okay with you?” He asks.

Smiling at him she responds,

“Yes, anything for you.”

Hearing the doorbell ring he comments that their meal has arrived. I will meet you at the dinner table.

Feeling incredibly horny and sexy, she dresses for dinner. She wondered if she should tell him about her massage experience. She didn’t want him to be jealous since she knew that someday he would fulfill her fantasy. Joining him at the dinner table he comments

“You look extraordinary, so beautiful and sexy. Let’s enjoy this lovely meal.”

Over dinner he asks her about her spa day, reluctant to share she vaguely says “it was amazing. I would like us to enjoy a couples massage some time It’s very relaxing.” Not pushing for details, he comments they will defiantly do that.

Finishing their dinner, he clears their plates and says,

“We have dessert, relax while I bring that out.”

Returning to the table with long stemmed strawberries and whip cream he asks her a question.

“Do you trust me darling?”

“Yes, of course why do you ask?” she asks.

Placing the plate of strawberries and cream in front of her, he says

“I want you to wear this.” Pulling a blindfold out his pocket.

“Are you comfortable doing this for me?” He asks.

She whispers “yes.”

Wondering what he had up his sleeve. After her massage all she wanted was for him to fuck her all night long. Placing the blindfold over her eyes, he says,

“Open your mouth.”

She submits. Placing a berry with whip cream in her mouth he whispers,

“Lick the cream.”

Circling her tongue around the tip of the berry, he whispers

“Now take a bite.”

Slowly biting, the juices from the berry dripping on down her lips.

“Good girl, now stand up.” He commands.

Unable to see, she doesn’t know what he will do next. He kisses her lips his hand placed on her breast and nipple, twisting her nipple, one and then the other, she whimpers. Kissing her neck, continuing to twist her nipple, she feels a hand on the other side of her, squeezing her breast and nipple. Her legs weaken, she moans. She had felt this earlier in her massage and realizes that Chris is making her fantasy come true. He whispers,

“Relax beautiful, this is your night. We are going to make passionate love to you all night. I am excited for you to experience this.”

Not knowing how to respond. She whispers,

“I am ready.”

Taking her by the hand, they lead her to the bedroom. Laying her down on the bed, they position themselves on either side of her. She thought their touch was familiar and wondered if Chris was the other person in her massage, she after all didn’t see who it was. They begin worshiping her body. One licking and sucking her nipples while the other licked and sucked on her pussy. She wanted to touch their cocks; he told her in due time. Propping he on her hands and knees, removing her butt plug Chris says,

“Straddle his cock.”

Submitting to her lover, she lowers herself onto the other man’s cock taking every inch deep inside of her. Chris positions himself behind her spreading her ass cheeks, he whispers,

“Are you ready for two real dicks?” Moaning,

“Yes please, I want to feel you inside of me.”

Entering her slow and gently allowing her to become comfortable. Her lovers make love to her slowly for about 10 minutes. The sensation of two cocks was unbelievable, she wanted to be fucked harder. Thrusting her hips back and forth, she moans.

“Please fuck me harder.”

Submitting to her request they thrust their cocks deep in her pussy and ass, pounding harder and harder, she screams,

“Ah, ah, yes, I am coming!”

Feeling their bodies jerk, both unloading deep inside of her ass and pussy. Whimpering, she says,

“That was amazing.”

Laying back on the bed with them on either side Chris asks her if she wants to remove her blindfold to see who he’s picked out. She does and much to her surprise it was Joe, the massage therapist.

“Wait, today at the spa was that the two of you who gave me a massage? She asks.

“Yes, it was, I made special arrangements for you so that we could give you your massage. I wanted to get you ready for tonight. Are you disappointed? Chris asks.

“I am not disappointed at all, today was amazing and I can’t wait to see where tonight goes. Thank you, my love.” She says.

Wanting to pleasure her every desire, they again suck her nipples while they both insert fingers in her pussy. They love watching her body respond as they fingerbang her pussy. Both insert a finger in her ass, sending her over the edge. He body quivers, she’s close to climax when they stop. “Darling, the night is still young, you must save your energy. And by the way, Joe will be here all weekend and we plan to pleasure you every chance we get.” Chris comments

“I am lucky girl. I have two sexy and handsome men at my disposal. I do hope that you will let me pleasure you both as well.” She says.

“Of course, darling, after all you give the best blow job I’ve ever had. Why don’t you show Joe how good your blow job techniques are.” Chris comments

Sitting between them, she takes a cock in each hand. Slowing stroking their cocks. Leaning over, she licks the tip of Joe’s cock while still stoking Chris. Taking the head of his cock in her mouth, Chris whispers

“Suck his cock baby.”

Both hands now on Joe’s cock, stroking him up and down, sucking the head she slides her mouth down his shaft. Joe’s places his hand on the back of her head gently, pushing deeper into her mouth, he moans,

“Fuck that feels amazing.”

Chris positions himself behind her, slaps her ass, inserting his dick into her pussy. Fingering her ass, he pushes hard forcing Joe’s cock to go deeper down her throat, she gags. Joe is ready to explode, it’s been a while since he’s had a blow job and she is an expert. Chris fucks her faster knowing Joe’s dick is going deeper down her throat. Joe yells out,

“Ah, ah, I am going to cum!”

Unloading his juices adored down the back of her throat, she keeps sucking. Chris meanwhile is ready to fill her pussy, yells out,

“Ah, ah, yes, (slapping her ass) I am going to cum.”

Swallowing the cum in her mouth she says,

“I love pleasuring you both, this is amazing. Chris darling, I want to suck your cock now. I know it doesn’t take you long to recover. Come here baby.” She says.

Sitting in between them again, both cocks in her hands. She wants Joe to fuck her while she sucks Chris and hopes he will recover quickly. His cock is slightly thicker, she loved how he felt inside of her. She loved being adored by these two men and wanted to pleasure them just as much. Chris is hard again, and Joe’s cock is coming to life. Getting on her hands and knees, she takes Chris’s cock into her mouth, still stroking Joe until he’s rock hard. Sucking and licking the length of his cock, Chris is moaning with desire. He tells Joe, to fuck her. She becomes a wild woman when she’s spanked and called a naughty girl.”

Getting behind her, Joe slaps one cheek and then another,

“Do you like this naughty girl?” he asks.

“Yes, I love to be spanked, please fuck me!” She orders.

Continuing to suck on Chris, Joe enters her pussy shoving his cock hard and deep. Thrusting her forward, Chris’s cock pushing deeper down her throat. Joe hasn’t had sex in a long time, and when he started fucking her fast and hard, she whimpers,

“Ah, yes harder.” She begs.

Sucking harder on Chris’s cock, he unloads deep down her throat. Joe still pounding her pussy, Chris whispers,

“That’s my naughty girl, take it deeper, fuck him.”

Joe still pounding her pussy hard and fast, just like Chris does when she’s been a bad girl. He can’t stop, he hammers her for a good 20 minutes, Chris watches while he sucks her nipples.

“Ah, ah, oh I am going to cum!” Joe screams out, one last hard push, his body shaking as he unloads deep in her pussy.

They fall onto the bed and Joe says,

“I am sorry if the was too hard. It’s been a while and I couldn’t contain myself. Chris, you’re a lucky man. You have yourself one hot, sexy, and sensual woman. Don’t let this one get away.”

“Man, I know, and I have no plans to let her get away.” Chris responds.

She snickers and says, “y’all are talking like I am not in the room.” They giggle.

She goes onto say, “I think it’s time for some more wine and a hot tub, how does that sound to you both.”

“Perfect” They both comment

While she was enjoying herself, she needed a bit of a break. She had just been fucked hard twice with no break in between. She wanted to check in with Chris to be sure that he was also enjoying himself. This was his idea, however she wanted to be sure he wasn’t having any regrets. Joe gets in the hot tub while she checks in with Chris.

“Are you enjoying yourself? Is this what you had hoped it would be? She asks.

“Yes of course I am enjoying myself. I shared with you that I wanted this for you. Are you enjoying yourself? Is it what you imagined it would be? How does it feel having two men fill your ass and pussy at the same time? I admit it was amazing watching you take us both and equally enjoyable watching you suck his cock while I fucked you.” He says.

Smiling at him she responds,

“Yes, I am enjoying myself, this is incredible. The sensation of both of you inside of me is better than I imagined. I feel so naughty yet sexy too. My naughty side just thought of something.” She says.

“What’s that beautiful?” He asks.

She shares her thoughts, “How would you feel about using our toy, you in my ass, the toy in my pussy, we could show Joe what that looks like. I would like to suck his cock at the same time, allowing you both to fill every hole in my body.”

“Holy fuck, seriously? You want 3 cocks, well two and the toy? Naughty girl, I love the idea; in fact, it crossed my mind too.” He says.

“Really? You mean that turns you on? Watching me with 3 cocks?” She asks.

“Hell yes, this is your weekend and I want to please you in every way possible. I think it would be incredibly hot and sexy watching you fucking 3 cocks even if one is a dildo, your wish is my command. It’s only the first night, Joe will be here all weekend, I can’t imagine what that naughty mind of yours will think of next.” He says.

“I hope to not disappoint either of you and hope that I don’t get tired out. I am sure my naughty mind will think of something else, like bending over your desk, while I suck his cock.” She adds.

“Damm woman, I cannot get enough of you. We should join Joe in the hot tub.” He says.

Joe comments he thought he was alone for a minute. Chris shares they were discussing what was happening, checking in on one another. “How are you feeling Joe? Are you comfortable with what’s happening?” Chris asks.

“Yes, I am comfortable. I admit that I was a little nervous coming into this. You both however made it comfortable and relaxing. I’ve never done this before, and it’s been a long time since I had sex. I am enjoying myself, thank you for thinking of me.” Joe says.

“I am glad that you’re comfortable. I am enjoying myself too.” She says.

“She’s so comfortable that she has a special request” Chris adds.

“What is that?” Joe asks.

“You’ll see and you won’t be disappointed trust me.” Chris says.

Aroused by them both, standing in the middle of the spa, cupping her breast, twisting her nipples for them she says,

“Do either of you want to suck these?”

Moving to either side of her, cupping her breasts, licking, and sucking her nipples.

“mmm, that feels good, suck harder please.”

She begs and didn’t expect what happens next. Her lovers clamp down on her nipples harder, gently biting which startles her.

“Oh, not so hard.” She whimpers.

“Do you like your nipples chomped on naughty girl?” Chris whispers

Whimpering, she whispers,

“Yes, I love my nipples nibbled on, please bite them, it makes me wet.”

Her lovers submit to her request, both biting gently while licking and sucking. The sensation brings on climax. Whispering,

“You’re going to make me cum.” She trembles.

“Wow, that was fucking hot.”

Joe says, Chris agrees and suggests they go in the house to play some more. Both of their cocks’ rock hard and ready for her. The settle in front of the fire with a bottle of wine while Chris fetches their toy.

“Our cocks are ready for you, get on your hands and knees naughty girl.” Chris demands.

Chris puts the toy on his cock, Joe watching not knowing what would happen next. Chris informs Joe this is the toy I was telling you about. She wants to suck your cock while I double fuck her with this, she wants to feel all her holes filled, so we will give this naughty lady what she wants. Entering her pussy with the toy and then her ass with his cock. She moans and says,

“Joe, come here, I want to suck your cock.”

Going slow allowing the sensation of having three cocks inside of her take control. Watching her suck his friend’s cock turned Chris on, he loves how sensual she is when she gives blowjobs. Slow and sensually, he pumps her with his cock and toy while she sensually sucks on Joe’s cocks. The three lovers moaning with desire before they whisper in sync that they are close to cumming. Picking up his rhythm, Chris rams her hard pushing Joe’s cock down her throat. Joe pushing deeper, unloading his nectar down her throat. Chris is close to climax, feeling her orgasm, he releases in her ass. Laying in front of the fire in silence, Joe was the first to speak.

“That was incredibly sexy, watching you take three cocks was mind-blowing.” Chris speaks up, “yes it was, how are you feeling sweetheart.” He asks,

“Incredible, I never imagined this would be so sensual. Feeling three cocks was so erotic.” She says.

“That’s some toy you have, do you guys use it often?” Joe asks.

Chris responds, “We have been using it regularly to prepare her for this. At first, I was reluctant, however I like using it on her as often as she wants which is frequently.”

“I do love it, but the real thing is better, you were right sweetheart.” She says.

Joe speaks up,

“Well, I am honored you asked me here this weekend. If you wanted to do this again after this weekend, I am in. This is the best time I’ve had in a long time; I am really enjoying myself and will always respect your boundaries.” He says.

She’s tired and suggests they retire for the evening. Adding,

“After all, we have 2 full days of playtime ahead of us.”

They agree, Joe goes to the guest room, while she and Chris settle in his. Holding one another tight, Chris asks her how she is feeling.

“I am a little tired, however I feel amazing. Tonight, was incredible and I am looking forward to the rest of the weekend.” She says.

She asks him how he’s feeling,

“Amazing, I am happy you’re enjoying your fantasy. It’s better than I imagined. The best part was watching you suck his cock while I double fucked you, I would love to do that again.” He says.

“I admit that was one of my favorite parts of the evening.” She says.

“What was the other part?” He asks.

“The blindfold, that was so erotic. Not knowing what you were doing was a huge turn on for me.” She adds.

The wheels in his head turning, the idea of adding another man to her fantasy crossed his mind. He wondered if he could pull it off. They drift off to sleep.

Final coming soon.