The Roommates Valentine’s Day Date
This story is a continuation of one of my previous stories. ‘Discover your roommate’s hidden treasures’. This story can be read by itself, but to really enjoy it, I suggest you read the previous story first. I hope you’ll enjoy them both.
The night it was decided.
She ended up asking Darla, Have you ever had sex?
She quickly replied, “No, I’ve never even been asked to.”
“Would you like to? I have a fantasy that I would like to see if you help me realize. It started the day you walked into Steve and me. I want to fuck your ass while you put up Steve’s dick. Steve and I have discussed it and he is ready if you are. Just for the record, he thinks your super-hot,” Shelly said, ending with a chuckle.
Cuddles up Shelly tighter, Darla bent her mouth through Shelly’s ear and said, Only if you take my virginity first before that.
Find the right time.
After it was decided that Shelly would take Darla’s virginity, the two of them were still looking for the right time, but being students, they were having trouble organizing this special moment together. Noel came and went. Darla had gone home to be with her father. Shelly and Steve had gone to spend time with his family.
After returning to school, Shelly and Darla had spent a lot of a night together, but Darla’s subject losing her virginity or the trio with Steve simply never came. It’s not that the girls had forgotten about it; it was just that they were always on the go with the classes.
As busy as they were, time slipped over and over again until it was February. It was then that the opportunity presented itself for them to realize Darla losing her virginity. Steve had to go home for a family emergency and wouldn’t be in town for Valentine’s Day. Shelly thought this would be the perfect time for her to take Darla’s virginity. So she made plans.
His first task was to make sure Darla didn’t intend to be with a guy that night. She knew she didn’t have a stable boyfriend. Why would she? She used to get cockwhenever she wanted to go home.
So the beginning of the plan, making sure Darla was available started on the Friday before Valentine’s Day. Darla walked into their room and Shelly was working at her office when she walked in. Darla approached and kissed her on the head and said, “Hi, you’re working hard.”
Shelly replied: “Paper due by the end of school on Monday and I don’t want to be stuck in this room all weekend working on it, although I probably will,” never preventing her fingers from clicking the computer keys.
After a few minutes, Shelly stopped and spun his chair around to see Darla. “Hey, what are you doing for Valentine’s Day? Special-type plans? Steve left until almost the end of February and I thought maybe we could go out together.
Darla groped with her bag back and stopped. She turned around so she looked at Shelly and said, “That’s a very good idea. Let’s make an appointment out of it.
“All right, this is a Valentine’s Day date for us.”
The two girls went back to do their own thing. Shelly clicks on the computer and Darla pulls stuff out of her backpack.
Shelly had made all the arrangements for their evening together and the two girls where excited. Shelly more than Darla because she knew how the night would end. With her slipping her cock deep into Darla’s virgin ass, we hope. Shelley had made all the preparations for her.
Shelley had made dinner reservations at one of the most chic places in town for them. When they arrived, they did quite the scene. Both wore sleeveless cocktail dresses that barely came mid-thigh, showing ample leg to everyone. The dresses were so shape-fitting you could see every curve of their bodies and they both ended up with four-inch heels. There was more than one edgy female Valentine’s Day date in the place with their guys looking at Shelly and Darla.
Dancing in a club near campus followed dinner. The girls danced with each other, sometimes standing close as lovers and other times they had male partners who constantly tried to cope with a sensation of their asses or breasts. They quickly became bored and decided to go home. It was fine with Shelly, it was still pretty soon things could develop between them tonight. They went back to the room and both wanted to get out of their dresses, but Shelley had a plan to put into action.
Just as Darla started slipping her dress, Shelly stopped her. “Let me do this for you since you were my date.” Shelly stepped up behind Darla and placed her hands on the little straps of the dress. She peeled them slowly on her shoulders. Darla raised her arms, allowing Shelley to slide the straps. Now all that held the dress on Darla was her tightness around her breasts.
Carrying her hands on Darla’s shoulders, she rubbed them gently before moving them in her arms and then on the sides of her body. She let them rest just at the top edge of the dress, slowly flexing her fingers over soft skin. After a break of a few more moments, she slipped her fingers under the edge of the dress and began to push it down.
The dress slipped along Darla’s skin, it’s the silky feel making her tingling. With Shelly’s constant pressure, he was moving down on her breasts until he slipped on her excited nipples causing a strong breath and a fiery tingle went straight to Darla’s. By the time she let her breathe, Shelly had pushed her to her hips. With just the little extra effort, the dress slipped beyond her hips and slipped to the floor in a ring of fabric around her feet.
Shelly, still standing behind Darla, moved near Darla’s ear and whispered, “Naughty, no panties tonight. I wish I’d known sooner. These whispered words made Darla shudder in excitement.
Shelly followed her whisper with a kiss to Darla’s earlobe before moving to the side of her neck. She was hanging out fucking along Darla’s neck as she moved her hands to the side of her breasts. She applied a smooth pressure as she moved them along the front sides, pushing Darla’s breasts together. Shelly ended up with her hands covering her nipples. She slowly worked her palms on them causing Darla to throw her head back in a long moan. Shelly continued to apply kisses around her neck while slowly working her nipples. She had moved her hands until she had Darla’s nipples between her fingers, rubbing, pinching and teasing them just to a bright pink red color.
Darla just laid her head against Shelly as she continued to kiss along her neck. The moans quickly escaped as she felt her body respond to stimulation on her nipples. She knew she was getting wet and if Shelly didn’t stop soon, she was sure to have a river of juice flowing inside her thighs soon.
Shelly felt Darla’s body begin to shake as she got ecstatic. With their heads so close Shelly leaned forward and grabbed the edge of Darla’s mouth in a kiss. Darla turned to her over for a fuller kiss, but he never got more than a sweet kiss at the edge of her lips. Shelly could tell Darla that she wanted more, just like her. Still holding Darla’s nipples from behind in her fingers, she guided her to one of the beds. Shelly made sure it was hers. She had arranged and placed everything she needed for the night at hand, but hidden.
When their legs touched the edge of the bed Shelly released her grip on Darla’s nipples and gave her a small push. Darla was unprepared to land with a thug on the bed. Before she could recover, Shelly reached down and grabbed her legs, pulling her to the edge of the bed. Shelly fell to her knees, spreading Darla’s legs and placing them on her shoulders. This left her looking right at a very excited that was flowing wet in excitement.
She knew exactly what to do with what was before and wasted no time. She slipped her tongue from the bottom up, making sure to slide through the clitré as she went. It was like a electric fire jolt through Darla. She flared off her hips to meet Shelley’s tongue. Shelly was ready for this after driving Darla crazy over the months to tongue and savor her.
She had placed her hands around Darla’s hips to prevent her from deflating, but she knew she had her right where she wanted it now. Shelly went straight to work on her, running her tongue through her lips before sliding it in and out as deep as she could. Occasionally licking her way back to Darla’s eye just to drive her crazy.
With Darla Going crazy to have an orgasm, Shelly decided it was time to move with her plan tonight. Reaching under the edge of the bed, she grabbed a small socket that she had lubricated and left there earlier. With Darla’s at the edge of the bed, it was the perfect position for her to slip it. She took Darla’s clitetme between her lips and sucked her. Just as Darla stood up against her. She took this moment to push the plug into her anus in a quick push.
Darla let out a cry of surprise and shock as he tried to get away from Shelly. Shelly quickly grabbed her and sucked her cliter even stronger as she ran two fingers into her. Darla’s screams turned into moans of pleasure as Shelly pressed her fingers deeply and worked them like a piston along the soft inner walls of Darla’s quickly leading her towards an orgasm forgetting all about discomfort intake.
This construction orgasm soon came. With a few faster pumps from her fingers, Shelly had her explosion in orgasm. Her juice flowed from her as if a tap had been turned on. Darla had never slapped and really hadn’t this time, but he was as close as you could come and not get there. Shelly’s hand and unrm were soaked by the time Darla had calmed down from her orgasm. Shelly couldn’t resist taking a few licks of her sweet juice before backing away from her.
Darla, lying on the bed with her chest rising, raised her head just enough to look at Shelly to ask, What did you slip into my?
“Oh, it was just an alnel take to help you relax for later.”
“Until later. Now come here and let me taste you,” Darla said while sitting on the side of the bed. She waved her buttocks a little feel the press plug in her, she sat down.
Shelly got up and dropped her dress to the floor in heaps next to Darla. Now she was there in just a pair of black lace panties with an obvious bulge for them and her heels. Darla reached out and acquired the front of her panties and pulled her closer. Taking her fingers and sliding them into the belt, she had her panties around Shelly’s feet in no time. Now Shelly was there with her cock coming out in her hardened state.
Darla wasted no time in taking her. She ran her tongue over the tasting head of her pre-cum before separating her lips to suck it all the way. She moved with one hand under her cock and the other drew up over his belly until he had a nipple pinched between his fingers. Darla knew exactly what Shelly liked and was going to give her in the most complete way possible.
As she let Shelly’s cock slide between her lips, she slipped her hand further between Shelly’s legs until she was at her anus. Darla had a bit of a surprise though, expecting to play with Shelly’s tight little opening, instead found she had an anal cap inserted already. She ran her fingers on the smooth flat surface before gently pushing over it. Yet, with the rooster in her mouth, she looked up at Shelly’s face. Shelley looked at Darla, smiling with a very conscious smile. Darla realized she had to have it all night.
Darla continued to work her cock and toy with the anal socket, pulling it partially and sliding it again. She had developed a little rhythm to her actions. Every time she let Shelly’s cock slide halfway and then as she slipped the anal cap back deep, she sucked her cock back with everything she could muster. This forced Shelly quickly to the edge; who at that time had her hands full of hair holding Darla’s head as she sucked her every time.
Shelly started controlling the tempo by pulling on Darla’s hair. She got closer and became more energetic and demanding by pushing in her mouth stronger each time. Darla, for her part, accommodated Shelly’s quick needs, while accelerating the game with grip. She was timing things to get him out as Shelly pushed him forward and pushed him back as she withdrew.
Finally, Shelly was overwhelmed and pushed as hard as she could against Darla, forcing her cock against the back of her throat before releasing her cum, filling Darla’s mouth. Darla swallowed as fast as she could without choking allowing only a little dribble to run around Shelly’s fast softening. Shelly backed away by pulling her dick from Darla, but she still had her hands entangled in her hair from the need for support to stay on her feet. She eventually untangles her fingers and collapsed on the bed next to her.
Darla scooted next to her and wrapped her arms around Shelley pulling her tight. She kissed him gently on the cheek, chin and finally on the lips. She could see Shelly was spent.
“If you’re too tired to continue tonight, he can wait until a later date.”
“No, I just need to rest for a minute,” Shelly replied, snuggling up to her. She liked to be naked against her roommate.
They were posing like this for quite a while before Shelley kissed Darla and asked, Are you ready to lose your virginity, that is? She laughed with that last little bit.
“For you, I’m so ready. Be gentle, Darla said with a laugh.
“On the hands and knees. I’m going to put a big pillow under you to help you support yourself.
Darla put himself on his hands and knees as indicated. Shelly set out to slip a large pillow under her that she could rest on all the experience. When Darla was installed, Shelly slipped her hand under the bed to gather the rest of what she had hidden there. This included a bottle of lubricant, a soft flesh dildo that was about seven inches long and two and a half inches thick, and a large hand towel.
She began by running her hands on Darla’s, gently massaging her cheeks. She worked her way inland until she parted with them to expose the valley of her. There was still comfortable in Darla’s was the socket. She grabbed the end of it and he waved slightly causing a moan to escape from Darla. She slowly began to remove it a fraction of an inch at a time. When she got it far enough that the widest point was right at the opening, she stopped. She picked up the lubricant and broke the open cap before pouring it around the socket. Just as it started at the pool, she slipped the cap leaving the lubricant to follow. She repeated it several times, making sure that a lot of lubricant was making its way.
Throughout this process, Darla moaned and wriggled. She looked over shelly’s shoulder and could see her focus on what she was doing. Every time she pulled him in part the impression that her was going to split, but as she felt the lubricant applied and she pushed him away, he felt so damn good. She knew there would be pain but also pleasure. They had talked at length about it, what to expect and what to do and what not to do.
Now that she was sure Darla was lubricated, she started pulling the plug until just the tip held her open. She put it back in place until the top of it rested against Darla’s flesh again. She repeated it for a while, allowing Darla to get used to it. All the while, she encouraged him to relax, not to squeeze.
She finally got out until the widest part was holding her open. She left it there as she lubricated the dildo until it was soaked with lubricant. While holding the dilet in one hand, she pulled the plug from Darla’s gaping hole, but before he could relax, she pushed the dilet by making him gasp at the greatest intrusion. Shelly took her hand and ran her behind her back and said, “Relax, baby, relax and let yourself adjust,”
Shelly gave her a few minutes to relax again before she started pushing the dilet deeper. She gently pushed it a little deeper and stopped before going further. Finally, everything but about an inch was buried in Darla’s. Clinging to her, Shelly began a gentle back-and-forth movement at first causing Darla to moan in both discomfort and pleasure.
She slowly increased the length of her movement until she pulled everything, but pretty much at the very end of darla’s movement before diving it back deep. Darla wriggled and moaned with the mixed feelings her lover gave her, but had no idea what was to come.
Shelly herself had become quite difficult to play with the toys as she prepared Darla’s for the ultimate moment of the night. As she worked the den in and out, she could see Darla was ready and she was so. Shelly had wanted to take Darla for a while and he was finally there. Pushing the dilet deeply, she left there as Darla moaned. Pick up the lubricant, she worked on her cock until it flowed. She knew it would be a good fit because the plumm was more grand that it was. She wanted Darla to let go to make her entrance less painful.
Once she was fully lubricated, she grabbed the base of the dildo and slipped it from Darla. Moving behind Darla, she grabs her hip with one hand and guide her cock to Darla’s open anus with the other. Leaning a little as she inserted her head, she whispered to Darla, “No more toys, it’s me.”
Darla, in a half moan, half-whispered said, “Yes, take me, I want to feel you.”
That’s all she needed to hear from Darla. She leaned forward pushing her cock past the outer ring of Darla’s anus, then with a little more force penetrated past the inner ring. She kept the pressure until she was as deep as she could go. Darla’s cheeks rested against her thighs.
Darla had moaned and wriggled all the time, but never utter a word to have her arrested. She has now deposited draped over her large pillow feeling as full as she had it all night. The difference was Shelly filling her and not a toy. She could feel her soft thighs resting against her. Finally turn her head to look back at Shelly, she said, “I’m ready for you.”
“Okay, baby, I’ll stop if you say stop.”
With this, Shelly began to move her hips back and forth gently sliding her cock into small strokes. She continued until she pulled almost all the way before pushing back completely. Darla was both panting through the discomfort and moaning in the excitement. Shelley built her moves until she freely fucked Darla’s ass. Every time she removed Darla moaning, every time she drove her cock forward, she pants up and grab the sheet on the bed.
It wasn’t long until Shelly felt near the edge of cumming, but she wanted Darla to sperm as well. She slipped a hand around Darla’s waist until she rubbed her. She felt for her clit/h and started rubbing in time to her cock driving in and out. This sent Darla to moan long and loud, which only encouraged Shelly more.
The end suddenly came for both. Shelly unable to hold back as deep as she could in Darla’s, while at the same time she pinched Darla’s clitoris sending Darla into a howling orgasm as well.
“Oh, damn it, I’m cumming!” Darla let go.
Shelly was unable to respond with her own cry because she was trying to cling to a bucking Darla as she came to the bottom of her.
When the two girls finally calmed down, Shelly was able to feel the moisture on her hand, arm and the fronts of her legs from where Darla was squirting during her orgasm. She could also feel her own sperm squeezing around her softening cock. She stayed there holding on to Darla for a few more moments before she collapsed out of her grip. This, in turn, pulled Shelly’s softened cock from her ass. When he came out, Darla just moaned as she curled up, pushing the big pillow out of the way.
Shelly, now free of Darla’s, collapsed next to her lover wrapping her arms around her. She pulled Darla tight lying at her and just held on as she calmed down. She finally gently said next to her ear, “Are you well, baby?”
Darla turned her head trying to look back at Shelly and said, “I feel wonderful. It was so much more than I expected.
They both laid cuddles together on the bed smelling of sex and relishing the sense of accomplishment.
After a bit, Darla flipped over to face Shelly. She leaned over and gave him a kiss before saying, “I think I’m ready to fulfill your fantasy with Steve.”
The date of Valentine’s Day roommateS