Jen left her boyfriend’s house early. Like usual. She enjoyed the sex they just had but was going to miss him on his business trip to Puerto Rico. She got in the car and drove away. By the time she got on 66 she noticed a note under the windshield wiper. That’s odd, people never left annoying flyers on her car when she stayed over. She grabbed it before merging onto 66 for the ride home. It wasn’t a flyer though. It was an envelope with her name typed on it. She was intrigued. She wanted to open it right now but was driving her usual 70 mph on 66. Speed made her wet and it helped that the wetness was mixed with the cum Steve just shot into her while they said goodbye in bed. She loved the feel of his cum in her panties. And how his cock fit into her so perfectly. It was a great way to start the day.
She pulled over in a parking lot for Harris teeter on 50. And opened the letter. In it was type written instructions on a single piece of paper. It said:
Surprise Mission. Today at 2 PM you will shower and shave carefully. You will then pack a bag with sundresses for four days. Heels, sandals, and two bathing suits. You are to report to Dulles Airport by 4:30 pm and board JetBlue Flight 2317 to San Juan PR at 6 pm. Your confirmation number KYXZUL. However prior to boarding the flight you are to use the women’s room next to gate B6. Go to the handicapped stall and open the panel on the right wall. You will receive further instructions then.
You giggle and think he has lost his mind. But this is such a romantic move. You have to go. And the thought of a resort with Steve in the Caribbean?! You immediately text Steve for details. He immediately writes back . . . ‘Follow the instructions. No panties. No bra and looking forward to our little adventure. ‘
So Jen makes arrangements to meet the deadline. She tells her family that the store she works for selected her for training. And she has to go. She then follows the instructions, shaving herself as smooth as she has ever been and plays with her swollen clit. The anticipation has made Jen feel so naughty. She throws her favorite sundresses in a carryon and picks her sexiest most comfortable shoes and heads to the airport. She breezes through security and heads for the bathroom. The handicapped stall is empty. And as the note described there is a panel. Jen pries it open. In there is a sealed box with her name on it. She opens it. ‘What’s your game Steve?!?!’
In the box is another letter. And also a vibrator. And lube. The letter says:
‘To ensure you have a good flight, I bought you this vibrator. Please insert it. Also please connect to the plane’s WIFI. The code is ‘SteveSmiles’. This vibrator is controlled by an app on my phone. While I am preparing witnesses I will be sending you pleasure. Can you be a good girl? Also a car will pick you up at the airport. He will have your name. Love you Fire.’
Jen was impressed and soaking wet. A four hour flight and Steve was in control. God she was horny. Would she cum on the plane? She immediately removed the vibrator and turned it on. It felt good. She turned and left as they boarded her flight.
As she waited in line the vibrator slowly started to work. And her legs became weak. A text came in from Steve. ‘Ready for your flight?’
Jen settled into seat 8A. Window. The vibrator in her pussy had stopped. She was relieved. It was going to be a long flight. And her lust was already maximized. She was going to see Steve and spend a few days in the Caribbean. And he had surprised her now. Twice. First with the trip then with the hidden remote control vibrator. Jen was already wet with anticipation and the hum of the vibrator nestled nicely in her pussy and up against her g spot was a nice distraction. Jen was seated next to a business man who looked her over twice and warmly smiled. He was in a very expensive suit. Has dark hair and gray eyes.
The plane started to taxi and Jen logged into the wifi network. Jens phone immediately vibrated. She received an IM from Steve. ‘Speed gets you wet doesn’t it?’
The plane began its run to takeoff. The planes speed exponentially increasing with the thrust of the engines. And the vibrator came to life. Strong hard pulsations resonating deep inside her pussy which seemed to be increasing with the speed of the plane. Jens nipples were immediately hard as the sensation from her pussy set each of her nerve endings on fire. Jen gripped the seat rest as the plane went faster and the vibration in her pussy increased. Jen was on the verge of having an orgasm, here in seat 8A. She ran her fingers down her bare legs adding to the pleasure as the plane left the runway. Beads of sweat rolled down her chest and down to her heaving breasts. The vibrator intensified. And Jen bit her tongue as she ground her how into the seat. The businessman looked over at her.
‘Are you ok?!’
Jen could barely breathe. ‘I’m fine’ she said breathlessly. ‘Just a little tense on take-off’. ‘Do you want to hold my hand?’ He said with a grin? As he said it the vibrator increased its speed. Jen’s juices were coating the vibe and were running down her pussy’s swollen lips. Jen just nodded. He reached his hand over and brushed her extremely hard nipple which was visibly poking through the flimsy fabric of the sundress. Jen moaned. And ground into seat to meet the intense vibration. Once the businessman’s hands met hers it became too much and Jen started to cum. She bit her lip as the waves of pleasure tore through her body. Her clit was swollen and her juices poured from her pussy as the pleasure overcame her. She stifled the moans and ground further into seat and rolled her eyes back. She gripped his hand tightly as the orgasm continued to roll over her. The vibration stopped at that point. And she was able to catch her breath. The stranger smiled and said ‘see flying isn’t that bad!’
He had no clue that he just helped Jen have her first orgasm of the trip.
Jens phone buzzed. An IM from her most evil boyfriend ‘I do hope you were able to keep quiet. You will be picked up at the airport by Marcos and Christina. They will have a sign with your name. Please be nice to them. They are looking forward to meeting you. They might take you sightseeing for a bit while I finish up my work here. Have fun with them.’
Jen fell asleep wondering what was in store next. And was a little upset that Steve wouldn’t be meeting her at the airport. But this was a work trip for him and so she couldn’t be too angry.
As Jen drifted off the cool air from the plane dried her sweat. She was roused from her sleep by a light throbbing from the vibrator. Like a heartbeat. And a text from Steve. ‘You are landing soon. And I can’t wait to see you later tonight. Have fun on your tour! ‘
What was he planning next? Her anticipation was growing. And her pussy started to moisten as the vibrator continued to pulse.
She was going to fuck Steve so very hard when she finally got to his room.
Jen exited her flight at San Juan precisely on time. It was 9 PM and the Caribbean air felt good on her skin as she entered the terminal. She was a little high from her orgasm at the beginning of the flight and the vibe was sporadically driving her to the edge. Steve was learning her body so very well. Just then Steve texted her. ‘Please remove the vibe before you meet Marcos and Christina.’ Jen needed to visit the restroom anyway and went and did as she was told.
She exited security and saw an extremely attractive couple holding a sign that simply said ‘Jen’. Christina was brown skinned, with striking green eyes and long flowing brown hair held in ponytail. She was about 5’6′ but in the black Blahnik closed toed pumps she was wearing she was easily 5’10’. She wore a short black pencil skirt cut high above her knees a white shirt and a black men’s tie. She had high cheekbones, beautiful teeth and was wearing black trendy glasses. Her body was beautiful. Full hips, long legs and ample butt and 38D breasts. Her nipples were hard as Jen always noticed such things. Marcos was equally hot. Lighter skin, about 6’3′ in black slacks a white button down shirt. He was well toned with a boxers build with a solid jaw, light brown eyes and an infectious smile. Jen thought these two would be fun to play with. She’d have to talk to Steve about that.
Both Marcos and Christina warmly greeted Jen like they knew her.
‘How did you know it was me?’ Jen asked.
‘Because Steve said his girlfriend was smoking hot’ said Marcos. ‘And clearly you are hot.’ Added Christina.
Jen was taken aback about the dual compliment. Christina bent down to pick up Jens bag at her feet. And while getting up inadvertently ran her fingers across Jens sopping wet upper thigh. The touch sent shivers down Jens spine and immediately sent her into arousal. Was that on purpose? Christina just smiled and Jen thought she might have winked at her. Jen made small talk in the back of the town car with the two divers sitting up front. their questions were pointed and mostly about Steve and her relationship. The first stop was to a beautiful bar overlooking the Caribbean. Next to the bar was a very dark portion of beach. No one from the bar could see onto the sand as it was surrounded by dunes.
Marcos went to drinks and Christina asked Jen to dance as salsa pulsed over the bar speakers. Jen complied. Christina grabbed her hand and brought her to the dance floor. Christina pulled her very close and immediately pressed her body and breasts against Jen as they danced rhythmically together. Jen was completely turned on. She hadn’t been with a woman in a while. And Christina seemed like she would make her cum in seconds. Jen moved her hands from Christina’s back down to her ass and pulled her body closer. They were rubbing their sex against each other. Christina let out a soft moan as her hands started to move to Jens breasts and nipples. She expertly began to tease Jen’s nipples and make them rock hard through the sundress fabric. Jen let out a soft moan when she felt two more hands around her waist. Marcos was dancing behind Jen and was grinding his now hard cock against Jen’s ass. He had a large dick and Jen knew that as long she told Steve every detail he would love for her to fuck them. So Jen deeply kissed Christina. Her tongue, soft and yet powerful, darted into her mouth. Christina nibbled on Jen’s lower lip and Jen moaned. Marcos kissed Jen next from behind while Christina attacked Jen’s neck. Jen was on fire. Her pussy was sopping wet. She had to see their bodies. Feel them. Christina seemingly read her mind and placed Jen’s hand under her skirt. Christina was smooth and dripping wet. Jen inserted two fingers into her new friend and Christina moaned loudly, her juices soaking Jen’s hand. Marcos grabbed Jen’s hand and licked it clean.
Marcos expertly took each of Jen’s fingers into his mouth and lightly sucked Christina’s nectar from those fingers. Christina feverishly kissed Jen’s lower neck and chest while grabbing Jen’s breasts. She clearly knew what she wanted. Christina grabbed Jen’s hand and Marcos and led them both away from the dance floor. Christina walked first and Jen loved to see the sway of her ass with the athletic toned legs and the red bottoms of the Blahnik pumps. Christina led the three of them out to the dock. And over to the isolated part of the beach. Except a double king sized blanket had been laid in the sand and tiki torches lit up the area. No one was around but Christina and Marcos likely had this planned. Was Steve in on this?
Christina kicked off her shoes and picked them up with her free hand. Marcos did the same. Jen followed suit. When the arrived at the blanket Jen immediately pulled Marcos close and kissed him deeply. His muscled arms pull her close to him. He had rock hard abs and based on the swell in his pants his cock would feel very good filling her pussy. Christina came up behind Jen and grabbed her sundress by the arms. Marcos grabbed the dress at the bodice. And Marcos and Christina violently pulled, tearing the sundress off of Jen’s body, leaving it completely in tatters on the sand. Jen let out a long lustful moan as the cool Caribbean air kissed her body. She was now completely naked in front of her new friends. As Marcos and Christina fervently kissed and licked Jen’s nipples Jen grabbed for Christina’s clothes. Jen popped the buttons on the white shirt Christina was wearing and unzipped the skirt. Christina was beautifully shaped and she wore a gold thong bikini bottom and lucky gold Victoria secret push up bra. Jen noted that the front of Christina’s panties was noticeably wet. Jen needed a taste but first Marcos. Jen and Christina attacked Marcos. Each of them kissing his lips, his neck and pulling at his shirt and pants. Once they removed his clothes Jen took in his body. He was chiseled. Had a military tattoo on his right arm, and had a long thick cock that was throbbing and probably about 10 inches. Did this guy do porn? He was hot and Jen decided right then that this would not be an encounter using condoms. She wanted to taste that cock and have him shoot his cum all over her face.
The flames from the tiki torches danced with the ocean breezes. The shadows created seemed to dance. Jen was thrown to the blanket by the two of them.
‘You are going to cum for us’ they said to Jen.
Marcos and Christina immediately attacked Jen’s body with their hands and lips and tongues. The two of them explored every inch of Jen’s skin causing her to writhe in pleasure, to moan asking for release. Marcos and Christina held each other’s hands as the started to lick Jen’s pussy. Christina hit Jen’s clit first and Jen moaned loudly and grabbed Christina’s hair holding her head firmly at her clit. Marcos had his tongue deep inside Jen’s pussy and he began to fuck her with his tongue. Both Christina and Marcos we using their hands to play with Jen’s completely erect nipples. The sensation was amazing. Jen was bucking her hips and moaning loudly. She started talking dirty ‘you are both going to make me cum! I’m so fucking close, don’t you dare stop!!’
But they did. They disengaged and and smiled and said she couldn’t cum yet. She needed to be filled with Marcos cock while eating Christina’s pussy. Jen attacked Christina and removed her bra and panties. Christina was hot. Her body was very womanly. She had beautiful curves in all the right places, a pin-up model fantasy. Her nipples were small and very hard. Jen took one into her mouth and Christina immediately began moaning loudly and bucking. She was extremely excitable. She moaned and swore in Spanish as Jen started to finger her. Marcos laid them both down and took his huge cock and started to rub it along Jen’s sopping wet pussy. Jen could feel the heat from his cock and the blood flowing through his cock. She needed to feel that cock inside of her. Christina straddled Jen’s face and Jen tasted Christina for the first time. He nectar was sweet. And her lust was undeniable. She immediately ground her pussy into Jen’s face, which was now soaking wet from Christina’s juices. As Christina’s first orgasm mounted Marcos stuck his massive cock into Jen’s pussy. He was huge but Jen was so wet that she could take it. She felt so full. As he began fucking her she moaned deeply into Christina’s pussy which drove her further toward her orgasm. Jen was out of control. Marcos was pounding her and Christina was grinding and Jen wanted to cum.
Marcos pulled out of her pussy. ‘I need to cum in your ass’. Jen moaned loudly as the salacious prospect of having that monster cock fill her ass with cum. He laid down and Jen laid on top of him with her back on his stomach. He then pushed his cock into her tight ass, the wetness from fucking Jen’s pussy easily coating him and making it easy to slide into her asshole. She moaned loudly as that huge cock slowly started fucking her ass. Christina got on all fours over Jen’s head so Jen could taste her pussy in between her screams of pleasure from having such a huge cock fucking her ass. Jen began to moan ‘I need to cum and I want some cum in my pussy.’
Christina dutifully complied and began to lick Jen’s clit. Expertly. Jen was on fire. She closed her eyes as her orgasm built. While her eyes were closed she felt a hand in her hair and cock slowly brushing her pussy and then exquisitely entering her pussy. She was being double penetrated. But she knew based on the hand in her hair who it was.
She opened her eyes. Steve was looking back at her. Smiling and lustful. He whispered in her ear, ‘surprise’. And he began to fuck her. And Marcos continued to fuck her ass. And Chrustinas tongue was firmly attacking Jen’s clit. Jen began screaming. She was cumming. Jen screamed ‘I’m cumming oh fuck I’m cumming’. Marcos and Steve both sweating profusely picked up their tempos. Steve was thrusting, his balls hitting Jen’s ass and his shaft being licked by Christina feverishly working Jen’s clit.
Jen started to cum. And she dug her nails into Steve’s back. And kept her legs locked around Steve’s waist. And she screamed as everything went white. Her orgasm overtook her. Flowing over her like the cool night air. As her orgasm began to subside Steve and Marcos tensed up and each came shooting their hot cum deep into Jen’s pussy and ass. Jen could feel both cocks cumming at the same time and she immediately had a second orgasm, she shook and screamed as she was filled. The sweat dripping down her body onto Marcos and Christina.
All of them collapsed on the blanket.