The night it was decided.

She finished by asking Darla, “Have you ever had anal sex?”

She quickly replied, “No, I’ve never even been asked to.”

“Would you like to? I have a fantasy I would like to see if you’ll help me fulfill. It started the day you walked in on Steve and I. I want to fuck your ass as you ride Steve’s cock. Steve and I have discussed it and he is willing if you are. Just for the record, he thinks your super-hot,” Shelly said, ending with a small giggle.

Cuddling up to Shelly tighter, Darla leaned her mouth by Shelly’s ear and said, “Only if you take my anal virginity first before then.”

Finding the right time.

After it was decided that Shelly would take Darla’s anal virginity, the two of them were always looking out for the right time but being college students, they were finding it hard to arrange that special moment together. Christmas came and went. Darla had gone home to be with her dad. Shelly and Steve had gone off to spend time with his family.

After getting back to school, Shelly and Darla had spent many a night together but the subject of Darla losing her anal virginity or the threesome with Steve just never came up. It’s not that the girls had forgotten about it; it was just that they were always on the go with classes.

As busy as they were, time slipped on and on until it was February. That’s when the opportunity presented itself for them to fulfill Darla losing her anal virginity. Steve had to go home for a family emergency and wouldn’t be in town for Valentine's. Shelly thought this would be the perfect time for her to take Darla’s anal virginity. So, she went about making plans.

Her first task was making sure Darla made no plans to be with some guy that night. She knew she didn’t have a steady boyfriend. Why would she? She was getting cock anytime she wanted at home.

So, the beginning of the plan, ensuring Darla was available began the Friday before Valentines. Darla walked into their room and Shelly was working at her desk when she came in. Darla walked up and kissed her on top of her head and said, “Hi, you are working hard.”

Shelly replied, “Paper due by end of school Monday and I don’t want to be stuck in this room all weekend working on it, even though I probably will be,” never stopping her fingers from clicking on the computer keys.

After a few minutes, Shelly stopped and spun her chair around to see Darla. “Hey, what are you doing for Valentine's? Any special guy plans? Steve is gone until almost the end of February and I thought maybe we could go out together.”

Darla was fumbling with her pack back and stopped. She turned around so she was looking at Shelly and said, “That is a damn fine idea. Let’s make it a date.”

“Fine, it’s a date for Valentine's for us.”

Both girls went back to doing their own thing. Shelly clicking away at the computer and Darla getting stuff out of her backpack.

Valentine’s Day

Shelly had made all the arrangements for their night out together and both girls where excited. Shelly more so than Darla because she knew how the night would end. With her slipping her cock deep in Darla’s virgin ass, hopefully. Shelley had made every preparation for it.

Shelley had made dinner reservations at one of the swankier places in town for them. When they showed up, they made quite the scene. Both were wearing sleeveless cocktail dresses that barely came to mid-thigh, showing ample leg to everyone. The dresses were so form-fitting you could see every curve of their bodies and they both finished it off with four-inch heels. There was more than one pissed off female Valentine's date in the place with their guys staring at Shelly and Darla.

Dancing at a club close to campus followed dinner. The girls danced with each other, sometimes holding each other close like lovers and other times they had male partners who constantly were trying to cop a feel of their asses or tits. They soon became bored and decided to head home. That was fine with Shelly, it was still early enough things could develop between them tonight. They got back to the room and both were wanting to get out of their dresses but Shelley had a plan to put into action.

Just as Darla started to slip her dress off, Shelly stopped her. “Let me do that for you since you were my date.” Shelly stepped up behind Darla and placed her hands on the dress’s small straps. She slowly peeled them down off her shoulders. Darla lifted her arms allowing Shelley to slip the straps clear. Now all that was holding the dress on Darla was its tightness around her breasts.

Bringing her hands back to Darla's shoulders, she gently rubbed them before moving them down her arms and then to the sides of her body. She let them rest just at the top edge of the dress, slowly flexing her fingers on the soft skin. After pausing a few moments longer, she slipped her fingers under the edge of the dress and started pushing it downward.

The dress slid along Darla’s skin, it’s silky feel causing her to tingle. With Shelly’s constant pressure it moved down over her breasts until it slipped over her excited nipples causing a sharp intake of breath and a fiery tingle went surging straight to Darla’s pussy. By the time she let her breath out, Shelly had pushed it to her hips. With just the little bit of extra effort, the dress slipped past her hips and slipped to the floor in a ring of cloth around her feet.

Shelly still standing behind Darla moved her mouth close to Darla’s ear and whispered, “Naughty girl, no panties on tonight. Wish I had known sooner.” These whispered words caused Darla to shiver in excitement.

Shelly followed her whisper up with a kiss to Darla’s earlobe before moving to the side of her neck. She was trailing kiss along Darla’s neck as she moved her hands to the side of her breasts. She applied smooth pressure as she moved them along the sides towards the front, pushing Darla’s breasts together. Shelly finished with her hands covering the nipples. She slowly worked her palms over them causing Darla to throw her head back in a long moan. Shelly just continued applying kisses around her neck all the while slowly working her nipples. She had moved her hands until she had Darla’s nipples between her fingers, rubbing, pinching and just teasing them to a bright rosy red color.

Darla just rested her head against Shelly’s as she continued kissing along her neck. The moans were escaping her fast as she felt her body respond to the stimulation on her nipples. She knew she was becoming wet and if Shelly didn’t soon stop, she was sure she’d have a river of juices running down the inside of her thighs soon.

Shelly felt Darla’s body start to shake as she got more excited. With their heads being so close Shelly leaned forward and caught the edge of Darla’s mouth in a kiss. Darla turned towards her more for a fuller kiss but it never got more than a soft kiss at the edge of her lips. Shelly could tell Darla wanted more, as did she. Still holding Darla nipples from behind in her fingers she guided her towards one of the beds. Shelly made sure it was hers. She had laid out and placed everything she needed for the night close at hand but hidden.

When their legs touched the edge of the bed Shelly released her hold on Darla’s nipples and gave her a small push. Darla unprepared for it landed 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 dropped to her knees spreading Darla’s legs and placing them over her shoulders. This left her staring right at a very excited pussy that was dripping wet in excitement.

She knew exactly what to do with what was before and wasted no time. She slipped her tongue from the bottom to the top, making sure to swipe across the clit as she went. This was like a jolt of electricity shooting through Darla. She bucked her hips to meet Shelley’s tongue. Shelly was ready for that having driven Darla mad over the months tonguing and savoring her pussy.

She had placed her hands around Darla’s hips to stop her from bucking but she knew she had her right where she wanted her now. Shelly went right to work on her pussy, running her tongue through her lips before slipping it in and out as deep as she could. Every so often licking her way back to Darla’s clit just to drive her mad.

With Darla going mad to have an orgasm, Shelly decided it was time to move along with her plan tonight. Reaching under the edge of the bed, she grabbed ahold of a small anal plug she had lubed and left there earlier. With Darla’s ass right at the edge of the bed, it was the perfect position for her to slip it in. She took Darla’s clit between her lips and sucked hard on it. Just as Darla reared up against her. She took that moment to pushed the plug into her anus in one swift push.

Darla let out a cry of surprise and shock trying to buck away from Shelly. Shelly quickly caught her and sucked her clit even harder as she ran two fingers into her pussy. Darla’s cries turned into moans of pleasure as Shelly pressed her fingers deep and worked them like a piston along the soft inner walls of Darla’s pussy driving her quickly towards an orgasm forgetting all about the discomfort of the anal plug.

That building orgasm wasn’t long in coming. With a few more fast pumps of her fingers, Shelly had her exploding in orgasm. Her juices were pouring from her like a tap had been turned on. Darla had never squirted and really hadn’t this time but it was as close as you could come and not get there. Shelly’s hand and arm were soaked by the time Darla had calmed down from her orgasm. Shelly couldn’t resist taking a few licks of her sweet juices before backing away from her.

Darla, laying back on the bed with her chest heaving, raised her head just enough to look at Shelly to ask, “What did you slip into my ass?”

“Oh, that was just an anal plug to help loosen you up for later.”

“For later?”

“Yes, later.”

“Until later then. Now come here and let me taste you,” Darla said while sitting up on the side of the bed. She wiggled her butt a little feeling the plug press into her ass she sat up.

Shelly stood up and let her dress fall to the floor in pile beside Darla’s. Now she was standing there in just a pair of black lace panties with an obvious bulge to them and her heels. Darla reached out and snagged the front of her panties and pulled her closer. Taking her fingers and slipping them in the waistband, she had the panties around Shelly’s feet in no time. Now Shelly was standing there with her cock sticking out in its hardened state.

Darla wasted no time taking it in. She ran her tongue over the head tasting her pre-cum before parting her lips to suck it all the way in. She moved one hand under her cock and the other traced up over tummy up her chest until it had a nipple pinched between its fingers. Darla knew exactly what Shelly loved and was going to give it to her in the fullest way possible.

As she let Shelly’s cock slip between her lips, she slid her hand further between Shelly’s legs until she was at her anus. Darla got a bit of surprise though, expecting to play with Shelly’s tight little opening, instead found she had an anal plug inserted already. She ran her fingers over the smooth flat surface before gently pushing on it. Still, with the cock in her mouth, she looked up at Shelly’s face. Shelley looked down at Darla, smiling a very knowing smile. Darla realized she must have had it in all evening.

Darla kept working her cock and toying with the anal plug, pulling it out partially and sliding it back in. She had developed a bit of a rhythm to her actions. Each time she let Shelly’s cock slip partway out and then as she slid the anal plug back in deep, she would suck her cock back in with all she could muster. This was forcing Shelly quickly to the edge; who by this time had her hands full of hair holding Darla’s head as she sucked her in each time.

Shelly started controlling the tempo by pulling on Darla’s hair. She was getting close and became more forceful and demanding by pushing into her mouth harder each time. Darla for her part was accommodating Shelly’s quicken need, while at the same time stepping up playing with the anal plug. She was timing things to pull it out as Shelly pushed forward and would push it back in as she pulled out.

Finally, Shelly was overwhelmed and pushed as hard 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 she could without choking allowing only a small dribble to run out around Shelly’s quickly softening cock. Shelly stepped back pulling her cock from Darla but she still had her hands entangled in her hair out of the need for the support to stay on her feet. She eventually untangled her fingers and collapsed on the bed next to her.

Darla scooted up next to her and wrapped her arms around Shelley pulling her tight. She gently kissed her on the cheek, chin and finally on the lips. She could see Shelly was spent.

“If you are too tired to continue tonight it can wait until a later time.”

“No, I just need to rest a minute,” Shelly replied cuddling tighter against her. She loved to be naked against her roomie.

They laid like that for quite a while before Shelley kissed Darla and asked, “You ready to lose your virginity, anal that is?” She giggled with that last little bit.

“For you, I’m so ready. Just be gentle,” Darla giggled back at her.

“Up on your hands and knees. I’ll put a big pillow under you to help support you.”

Darla got on her hands and knees as instructed. Shelly set about slipping a large pillow under her that she could rest on during the whole experience. When Darla was settled Shelly slipped her hand under the bed to gather up the rest of what she had hidden there. This included a bottle of lube, a soft flesh-like dildo that was about seven inches long and two and a half inches thick, and a large hand towel.

She started by running her hands over Darla’s ass, gently massaging the cheeks. She worked her way inward until she was parting them to expose the valley of her ass. There still snug in Darla’s ass was the anal plug. She grasped the end of it and wiggled it lightly causing a moan to escape from Darla. She slowly started pulling it out a fraction of an inch at a time. When she had it out far enough that the widest point was just at the opening she stopped. She picked up the lube and snapped the cap open before pouring some around the anal plug. Just as it started to pool, she slid the plug back in allowing the lube to follow. She repeated this several times, making sure plenty of lube was making its way in.

During this whole process, Darla was moaning and Squirming. She was looking back over her shoulder at Shelly and could see her concentration on what she was doing. Each time she would pull it partially out felt like her ass was going to split but as she felt the lube applied and she pushed it back in, it felt so damn good. She knew there would be pain but also pleasure. They had talked about it at length, what to expect and what to do and not do.

Now that she was sure Darla was lubed, she started pulling the plug all the way out until just the tip was holding her open. She would slide it back in until the top of it was resting against Darla’s flesh again. She repeated this for a while, allowing Darla to become used to it. During this whole time, she was encouraging her to relax, not to clench.

She finally pulled it out until the widest part was holding her open. She left it there as she lubed the dildo until it was soaked with lube. While holding the dildo in one hand, she pulled the plug from Darla’s gaping hole but before it could relax, she pushed the dildo in causing her to gasp at the larger intrusion. Shelly took her hand and ran it down her back saying, “Relax, baby, just relax and let yourself adjust,”

Shelly gave her a few minutes to relax again before she started pushing the dildo deeper. She gently pushed it a little deeper and pause before going further. Finally, all but about an inch was buried in Darla’s ass. Holding onto it, Shelly started a gentle back and forth motion at first causing Darla to moan in both discomfort and pleasure.

She slowly increased the length of her motion until she was pulling all but about the very end of it from Darla before plunging it back in deep. Darla squirmed and moaned with the mixed sensations that her lover was giving her but had no idea what was still to come.

Shelly herself had become quite hard playing with the toys as she prepared Darla’s ass for the ultimate moment of the night. As she worked the dildo in and out, she could see Darla was ready and so was she. Shelly had been wanting to take Darla anally for some time and it was finally here. Pushing the dildo deep, she left there as Darla moaned. Picking up the lube, she worked it all over her cock until it was dripping. She knew she’d be a nice fit because the dildo was larger than she was. She wanted Darla loose to make her entry less painful.

Once she was fully lubed, she grabbed the base of the dildo and slipped it from Darla. Moving up behind Darla, she gripped her hip with one hand and guide her cock to Darla’s open anus with the other. Leaning down a bit just as she inserted the head, she whispered to Darla, “No more toys, this is me.”

Darla, in a half moan, half-whisper 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 and then with a bit more force penetrated past the inner ring. She kept the pressure on until she was as deep as she could go. The cheeks of Darla’s ass were resting against her thighs.

Darla had moaned and squirmed the whole time but never uttering one word to make her stop. She now laid draped over her big pillow feeling as full as she had all night. The difference was it was Shelly filling her ass and not some toy. She could feel her soft thighs resting against her. Finally turning her head to look back at Shelly, she said, “I’m ready for you.”

“Okay, babe, I’ll stop if you say stop.”

With that, Shelly started moving her hips back and forth gently sliding her cock in small strokes. She continued until she was pulling almost all the way out before pushing back in fully. Darla was both panting through the discomfort and moaning in the excitement. Shelley built up her movements until she was freely fucking Darla’s ass. Every time she pulled back Darla moaned, every time she drove her cock forward, she would pant and grasp the sheet on the bed.

It wasn’t long until Shelly felt herself nearing the edge of cumming but she wanted Darla to cum as well. She slid a hand around Darla’s waist until she was rubbing her pussy. She felt for her clit and started rubbing it in time to her cock driving in and out. This sent Darla into moaning long and loud, which only encouraged Shelly more.

The end came suddenly for both of them. Shelly unable to hold back any longer pushed as deep as she could in Darla’s ass, while at the same time she pinched Darla’s clit sending Darla into a screaming orgasm as well.

“Oh, fuck I’m cumming!” Darla let loose.

Shelly was unable to answer with her own scream because she was trying to hold on to a bucking Darla as she came deep in her ass.

When both girls finally calmed down, Shelly could feel the wetness on her hand, arm and the fronts of her legs from where Darla squirted during her orgasm. She could also feel her own cum squeezing around her softening cock. She stayed there holding on to Darla for a few more moments before she just collapsed out of her grip. This, in turn, pulled Shelly’s softened cock from her ass. When it popped out, Darla just moaned as she curled up, pushing the big pillow out of the way.

Shelly, now free of Darla’s ass, collapsed next to her lover wrapping her arms around her. She pulled Darla tight to her and just held her as she calmed down. She finally softly said next to her ear, “Are you alright, babe?”

Darla turned head trying to look back at Shelly and said, “I feel wonderful. That was so much more than I expected it to be.”

They both laid cuddled together on the bed smelling of sex and savoring the feeling of fulfillment.

After a bit, Darla rolled over to face Shelly. She leaned in and gave her a kiss before saying, “I think I’m ready to fulfill your fantasy with Steve.”