Loading...Brad sat on the floor in his darkened room. Across the narrow side yard that separated their houses, the sheer curtains in Ann’s room were not quite closed, and the light in her room made them almost transparent. Brad waited, patiently.
A few minutes later he was rewarded, as Ann stepped out of her bathroom, toweling her short brown hair dry. Naked, she walked across the room and stopped in front of her dresser. Brad reached down and began gently stroking his penis.
He’d known Ann since they were children and he’d watched her grow up through this very window. They’d never said anything about it, but neither of them had ever gone out of their way to really close the curtains in their respective rooms. Over the years it had become kind of a ritual. On Tuesdays and Thursdays Ann watched Brad. On Mondays and Wednesdays he watched her. The rest of the week it was catch as catch can. Now that they were in college, if they knew each other had come home to visit, they’d alternate nights.
Brad’s penis grew erect under his ministrations. All the way through high school, Ann really hadn’t been much to look at – 5’6″, stringy brown hair, a pug nose, small breasts and boyish hips. She’d always dressed plainly – jeans and a t-shirt or simple blouse and a modest skirt, white briefs and white bras – not that she’d really needed a bra. On Sundays she’d wear a dress to go to church, but they didn’t do much for her figure. She was just the girl next door who didn’t seem to mind if the boy next door watched her undress and masturbate occasionally.
Brad was pretty much the same. Light brown hair cut short, about 5’10” and 150. Not terribly muscular, but Ann had always thought he had a cute butt.
College had changed them both. Brad’s roommate had grown up lifting weights, and he had talked Brad into coming to the gym with him regularly. Over the year Brad had put on a little weight, mostly muscles, and had filled out and defined his body a bit more. Ann had always been a jogger, so she was fit, but she had filled out too during her freshman year, and her roommate had taught her about wearing a little subtle makeup and had refined Ann’s clothes shopping habits.
Brad gasped as Ann turned toward the full-length mirror in corner of her room. He could see her almost full on now. She really had filled out. Her breasts were still smallish, but now they were full and round, standing out prominently from her chest, capped with light brown nipples. And, even more to his surprise, Brad could see that Ann had trimmed her pubic hair pretty short. When he had watched her during high school she it had been almost bushy between her legs. Now it was short and, he thought, may have been completely shaved from her labia. He was stroking himself steadily now, his penis long and firm in his grip.
“Ok,” Ann thought to herself, “here comes the show.” She pulled back the bedspread and covers from her bed, propped up the pillows against the headboard, and sat down on the bed.
“Oh, god,” Brad thought. “She really is shaved. And there she goes. Oh god, oh god, oh god.” His fist pumped rapidly up and down his penis as he stared at his neighbor.
Ann had leaned back on the bed, which faced the window, spread her legs, and begun to masturbate. With her left she pinched her nipples into erection, alternating between left and right breast, teasing and caressing them, feeling the erotic sensations run through them and down toward her crotch.
She caressed her nether lips with her right hand, coaxing the lubrication from within her, urging the inner lips to blossom open.
Brad was up on his knees now, pumping furiously at himself. Ann had snaked a finger between her lips and into her vagina, then slowly pulled it out, brought it to her mouth, and sucked it. She knew he was watching, and was getting a perverse pleasure from teasing him a little.
With her left hand she spread her labia open, exposing her vagina and clitoris. Brad watched intently. She dipped two fingers of her right hand into her vagina, lubricating them, and then applied them to either side of her clitoris. She began rubbing them alongside her clitoris, sending little shocks of pleasure through her loins.
Brad paused. He was close, but wanted to wait. He watched as Ann’s eyes closed and her mouth dropped open. Her right hand rubbed steadily. Brad resumed stroking himself.
It was going to come fast tonight, thought Ann. It usually did, at least the first one, when she had an audience. She rubbed herself a bit more firmly, and then her hips arched up, demanding more. She rubbed even harder, and her orgasm began, not a big one, but a solid, satisfying one. It rippled through her loins, gripping and releasing her, a firm, relaxing release. She stopped rubbing and cupped her sex with her hand, trying to hold on to the last moments of her orgasm as her hips relaxed down onto the bed.
When Ann’s hips had risen up off the bed Brad had begun pumping himself furiously, and soon a long, thick stream of semen raced through his body, up his urethra, and burst forth from him, splattering across the floor. He panted from the effort, and then released his clenched fist from around his penis. He looked up to see Ann roll over on her side and turn out the light, ending the evening’s show.
“Wow, that was hot,” said Teri, getting up from the easy chair that sat against the wall in Ann’s room, out of the view from Brad’s window. She lay down in the bed next to Ann. “And you say you’ve been doing this since you were kids? And this is all it is? You’ve never done anything more?”
“Yeah,” said Ann. “It’s kind of an unspoken thing. I mean, I caught him looking at me when we were about 12, and something inside me thought it was really exciting that he wanted to look at me. And then, one night not too long after that, I decided to try and watch him. I saw him a few nights later. It was kind of sexy, at least 12-year old sexy. Anyway, I started leaving the lights on and the curtains kind of open, and one day rearranged the room so the bed faced the window. I told my Mom I just liked the light coming in the window in the morning.”
“So when did you start masturbating for him?” Teri asked.
“It was really a mutual kind of thing. I think he probably started. It was a year or so after we’d started watching each other. He just stood there one night, pulling at himself. I didn’t know what he was doing at first, but I figured it out when he came. After he’d done it a few times I screwed up my courage and did it for him. I’d only done it a few times before that. I even snuck into my parents’ room when they weren’t home and would read the marriage manuals they had hidden in the closet. One of them was just about women, and had a whole section about masturbation. I practically memorized it I read it so much. And when I first started, I tried to do it just right so Brad would think I knew about sex and stuff.”
“So you’ve been jack and jilling ever since, and never had the guts to go further,” said Teri.
“Well, we did go out a little last summer, before we left for college. But he’d never do much more than give me a kiss and a hug goodnight, and then we’d both go to bed and masturbate for each other. It was easier that way.”
“Well it’s time, Ann, that you did something more with him. I looked at him today when you pointed him out at the mall. He’s a hunk.”
“I’d be too embarrassed, Teri. He’s… he’s Brad. The boy across the yard.”
“Look, sweetie. You’ve had a lot of experiences this year. When you got to Smallville College about the only thing you knew about sex was masturbating. Now you’ve got a female roommate you make love with regularly. You’ve been to, and were a star of, a jack and jill party. You’ve even helped me suck off George and then sat on his face and he ate you out while I sat on his cock and had a good fuck.”
“But, it’s Brad. He’s my buddy.”
“All the more reason. He’s your buddy. You’ve displayed yourself to him at one of your most intimate moments. Repeatedly. So now you take it to another level. We’ll make your first time amazing. For both of you.”
“Well…, maybe not our first time.”
“What do you mean?” asked Teri. “Have you been holding out on me? Have you and he…”
“Well, yes, once,” said Ann. “Right before we left for college. Somehow, both of our parents were away one weekend. Mine had to go visit Great Aunt Millie. His father had some business thing, and took his mom. We went to dinner, and then a movie. When we got back he did the kiss and hug thing, but I grabbed his hand when he went to leave and brought him up here. I’d kind of been thinking about it, and had bought some condoms just in case. Anyway, we got up here and he undressed me and I undressed him, and I put a condom on him, and we made love. It was kind of awkward, but it was kind of sweet, too. We didn’t say much afterward, but it kind of punctuated everything.”
“Some punctuation,” Teri replied. “Ok, so that makes me feel a little better. We’ll just be initiating him into anal and group sex, not sacrificing y’all’s virginity.”
“I don’t know how he’ll feel about being with both of us,” Ann worried.
“It’s a standard guy fantasy,” said Teri. “And anyway, I’ll bet he’s never seen you with a strap-on.”
“We’re not going to do that,” gasped Ann. “I mean, do you really think…”
“Yes, I do,” said Teri. “Look, you know getting it in the ass is fabulous. You have to use a lot of lubricant, and be relaxed, but you know you’ll really like it. I’ve seen how hard you cum when I just put a little vibrator in your ass while I’m eating you out. And turnabout is fair play. If his cock is going to be in you and me, front or back, he’s got to experience it too. I’ve always wanted to make a sandwich with a guy in the middle. If I’d known you weren’t a virgin I’d have made you do it with George and me. So Brad is going to get to be with you again, which I bet he’s been thinking about since that night last summer, and I bet you have too, I get to fulfill a fantasy, and we all get to have fun.”
“You’re too much,” said Ann. “Come here.”
She embraced her roommate and gave her a long deep kiss. They embraced and began caressing each other.
Their bodies were similar in many ways. Terri was a little taller than Ann, but not by much. Her hair was blonde and her eyes green, and she had shaved her pubic hair as well. Her breasts were firm 36 B’s, as opposed to Ann’s almost 34 B’s. Their nipples and surrounding areolas were larger and pink. When she was excited, which she was rapidly becoming as Ann began to stroke her fanny, her nipples became incredibly sensitive. She could almost orgasm just from having her nipples stroked and sucked, and Ann knew this.
Ann slipped down her friend’s body and began to lick Terri’s nipples. After she had stroked them into erection, her mouth fastened on to the left one, sucking it deep into her mouth and teasing its tip with her tongue. Her left hand focused on Teri’s other breast, caressing it gently, circling the nipple and then flicking at it gently. Teri began to moan quietly.
Ann continued to play with Teri’s breasts, occasionally switching from one to the other. Terri had surrendered to the erotic sensations, gently caressing Ann’s head and back as her arousal heightened.
Suddenly it was just too much. Terri pulled her friend up and over her, their mouths locking together in a kiss. As their tongues wrestled together, Teri spread her legs a little. Ann slipped her thigh between Teri’s and pressed herself firmly against Teri’s crotch. They began to rub against each other, their labia slipping and sliding against the firm thigh. Not long later Teri’s orgasm overtook her, rumbling through her loins. She pressed herself hard against Ann, grinding her crotch hard against Ann’s leg. Ann’s body was quick to follow, and the pair trembled in each other’s arms as they surrendered themselves to the physical pleasure that engulfed their bodies.
They fell asleep that way, Ann cradled in Teri’s embrace, their mouths pressed hard together, their legs intertwined
Teri rose early the next morning, a plan forming in her head. The first thing she did was to carefully close the curtains, then she headed for the bathroom to get ready for the morning.
Ann awoke as Teri came out of the bathroom.
“Good morning,” she said. “Why are the curtains closed?”
“I’ve got a plan.”
“A plan for what?”
“A plan for how we’re going to introduce your buddy next door to the wonders of group sex.”
“And how, pervert, do you plan on doing that?”
“Pervert yourself,” Teri replied. “Get dressed and I’ll tell you over breakfast.”
Ann rolled out of the bed and went to the bathroom to pee, wash her face and brush her teeth. Ten minutes later she emerged from the bathroom. She dressed and she and Teri went to the kitchen for breakfast.
“Ok,” Ann said when they were sitting together over the remains of breakfast. “What’s this plan of yours?”
“First, are you sure your parents aren’t coming home today?”
“Yeah, I am,” said Ann. “When I talked to Mom last night she said that her sister still wasn’t doing too well so they were going to stay for a few more days.”
“All right then. I’m going to work on that paper today. I’m going to stay in the house and away from the windows. The idea is that I don’t want Brad to know I’m here.”
“Ok,” said Ann, “then what?”
“You’re going to spend the afternoon with Brad. Go over there and get him to take you out. Go to the mall, go to a movie, whatever. Just don’t come back until after you’ve had dinner.”
“And?”
“Bring him back here. Make sure you’ve been flirting with him. Maybe let him get a look down your shirt. He’ll probably notice you’re not wearing those big white gramma bras anymore. That’ll probably get his attention. Maybe talk a little about me – about how I’m a little wild and how I taught you some things. Get him nice and horny.”
“Ok, so I’m supposed to tease him and then bring him home. Then what?”
“Bring him up here. Get naked. Then masturbate for him with that new toy I brought. It will be in your nightstand.”
“You want me to stick that two-pronged thing in me? In front of him? I’d die!”
“No, lover, you won’t” said Teri. “It’s going to be great. Just tell him you’ve learned some things, especially about yourself, and you want to show him in person.”
“Well, then what? And where are you going to be when all this is going on?”
“I’m going to be in your closet, watching. I’m going to be naked, and I’m going to have the strap-on on, but just with the little pointy dildo in it. I don’t want to scare him too much when I come out.”
“What are you going to do?” asked Ann.
“After you give him your show, and I want you to talk to him about how good it feels to have something in your ass, I want you to make love with him. I brought plenty of condoms. They’ll be in your nightstand drawer. Do it missionary style. I want him on top of you when I enter the scene.”
“When you enter the scene,” Ann said skeptically.
“Yes, enter the scene,” Teri replied. “When I come out I want you to throw your arms and legs around him and hold him tight. I’m going to come up behind him, lube him up good, and then I’m going to take his anal virginity while he’s doing you. I’ll be quiet, but when I put that finger with a big glob of lube up his butt he’s going to jump. That’s why I want you holding onto him, tight. He’s going to jump, but you’ve got to keep him occupied and focused. I’ll have that little dildo dripping with lube, too, so it should go in him pretty easy.”
“I don’t know about this. Brad’s pretty strong,” said Ann.
“That’s why you’ve got to get him really horny,” said Teri. “I want him wanting you and your hot little pussy so bad that he’ll do just about anything to get it – even let your more than friendly college roommate do him in the ass with a strap on.”
“You know, this scares me and makes me horny all at the same time,” said Ann.
“Good,” replied Teri. “Now let’s get your room ready for tonight’s little threesome.”
Ten hours later Brad and Ann pulled up in front of the house.
“Come on in with me,” said Ann. “We can watch some TV, or something…”
“Well, all right,” said Brad. He didn’t really know what to think. Ann was certainly different. They’d spent the afternoon just wandering around, talking about freshman year of college, and how things had gone. It seemed to Brad that Ann’s year had been a lot more interesting than his. Her roommate, Teri, sounded pretty entertaining. When they were alone in the park Ann had asked him if he wanted to know how that intern had seduced the President. When he asked what she was talking about she’d pulled down the back of her pants and shown him she was wearing a thong. This was Ann, the girl next door, the girl who always wore big white panties, not sexy little thongs. And he could see through her white blouse that she was wearing a pretty skimpy little blue lace bra.
“Come on in, big boy,” Ann whispered huskily at him.
Brad stared, his mouth dropping open. What was going on?
Ann burst into laughter. “You should see yourself. I can’t believe I said that. I can’t believe your chin just hit the ground. Come on, let’s see what’s on TV.”
She took Brad by the hand and led him into the house.
“Where are your parents?” Brad asked.
“They went to Millersville. My aunt just had an operation, so they went to help out for a few days.”
“Oh. So what do you want to do?” he asked.
“This.” Ann put her arms around Brad’s neck and kissed him, hard.
“What’s that all about?” Brad asked a few minutes later when Ann released him.
“I’ve been thinking about last summer. The end of last summer. I’ve missed you a lot. And I want to be with you again.”
“You do?”
“Yes,” Ann replied. “Come on.” And with that she turned and walked over to the stairs, slowly unbuttoning her blouse as she went. Brad followed her up the stairs and to her room.
When they got there Ann made Brad sit in the chair. “I want to show you something, first” she said.
“What?”
“Just watch. But take off your clothes.”
Brad stood up and pulled his shirt over his head. Ann had dropped her blouse at the top of the stairs and now unhooked her bra. It unfastened in the front, and Brad watched, fascinated, as her small round breasts were unveiled. They watched each other as they stripped off their pants and underwear. Brad sat back down in the chair. His penis was erect, jutting up from his lap. He absentmindedly stroked it as he watched Ann.
Ann walked over to the night table. Her closet was against the wall on the other side of the bed, and she could see that Teri had left the louvered doors opened just a crack. She opened the drawer, pulled out the double-shafted vibrator, two condoms and a bottle of lubricant.
“Teri gave me this to keep me company during the summer,” Ann said. “I want you to watch me use it for the first time.”
“Umm, ok, I guess,” said Brad. The thing in her hand was obscene. He couldn’t believe that shy little Ann was about to demonstrate it for him.
“Come sit at the end of the bed,” Ann asked. Brad did as he was asked. Ann rolled the condoms down the silicon shafts and then anointed them with the lubricant, and then herself. Brad watched, fascinated, as her finger disappeared up her anus.
“Doesn’t that hurt?” he asked.
“No, it feels nice. You kind of have to get used to it, but it’s nice.” She switched on the vibrator and it’s low hum filled the room. “Actually, I’ve gotten pretty anally erotic over the year. At first I thought it was disgusting, but it really feels pretty good once you get used to it. Now just watch.”
Ann leaned back and began to caress herself with the toy, rubbing it over her breasts, and then down over her stomach and across her mound. It felt great.
Actually, Ann couldn’t believe she was doing this. She could see Brad’s penis growing long and hard. It sprouted from a forest of dark curls at that spread up over his belly, almost to his navel. She ran the double-shafted toy over her sex again. She felt herself lubricate as its insistent buzz ran through her. “I really can’t believe this,” she thought to herself. “Teri really has changed me. But god, look at his dick. It’s so long – it looks so good. It felt so good. All right, just do it.”
Ann stopped analyzing what she was doing and just started. She placed the tips of each shaft at her openings, and slowly pushed it into herself.
“Oh god,” said Brad. “You’re putting it in you!”
“Shhh,” said Ann. “Just watch.”
Slowly she pressed the toy into herself, filling her vagina and rectum with the buzzing shafts. It was really quite pleasant, and she felt full. She could also feel the shafts sending their insistent vibrations through, and as she manipulated the toy, the shafts rubbing against each other a little through the membranes separating her vagina and rectum. With her left hand she began rubbing her clitoris.
Brad watched, amazed. Here was the girl next door, the girl he’d watched all these years, the girl who made love with him for the first, and only, time in his life. And here she was, her legs spread wide open, not more than a foot from him, pushing the most obscene sex toy he’d ever seen deep into herself, and not just in her vagina, but up her ass as well. And she looked like she enjoyed it!
Ann slid the toy out of herself, savoring the sensations that ran through her. Just before it exited her totally, she slid it back in. When it hit bottom, she turned the controls up to high. The buzz filled her. Her fingers worked at her clitoris more quickly.
Slowly she developed a rhythm. She slid the dildo in and out and rubbed her clitoris. She watched Brad as he stared at her. She could see him rub the precum from the tip of his urethra around the tip of his penis.
Like the night before, her orgasm built slowly and wasn’t earth shattering, but was solid and enjoyable. Her hips arched up and she drove the dildos deep into her orifices. Her fingers were a blur around her clitoris. “I’m cumming, I’m cumming,” she announced to Brad.
Brad had never been this close to a woman in orgasm, except for that one night he had made love with Ann and then he wasn’t really watching her. He saw her nipples grow hard and tight, and a flush come over her chest and breasts as she called out. She was holding the vibrator hard against herself. A few minutes later she was quiet, and he moved next to her.
“Take it out of me,” she asked him.
Brad grasped the base of the dildo and gently slid it out of Ann. He watched as the lips of her vagina stretched out to hold on to the shaft as it slid out, as if they didn’t want to let it go. The toy glistened with a combination of the lubrication she’d spread on them and her own juices. He put it on the bed next to them.
“Kiss me,” Ann asked. Brad leaned over and kissed her, holding her tight against his chest.
Slowly they moved into the act of love, kissing and caressing each other. Brad caressed and then sucked on Ann’s breasts, bringing her nipples back to erection. Ann slid down, sucked his nipples, then moved down further, briefly sticking her tongue in his navel, and then kissing, caressing and sucking his penis.
Brad was overwhelmed. He’d fantasized about this kind of thing, but it had never happened to him. In truth, he was kind of shy, especially around girls. Ann was the only girl he’d ever done anything with, and that was mostly at a distance, except for that one night that he’d really thought was only going to happen that one time.
“I want you in me,” Ann said, looking deep into his eyes.
“But..” Brad stammered.
“There are condoms in the nightstand. Put one on.”
Once again he did as he was told. When he was properly sheathed, he moved between Ann’s legs.
Ann reached down and guided him into her vagina. It felt so wonderful. She’d used vibrators and dildos, especially because Teri had made her and then just because, but they weren’t at all like this. Brad was hard and soft and warm and firm all at the same time. She pulled him to her and kissed him deeply as his penis filled her vagina.
Brad started slowly, sliding gently in and out of Ann. “She’s hot,” he thought. “Her vagina is hot. This feels so good. Be gentle. Don’t go too quick.”
A few minutes later Ann glanced over and saw Teri step quietly from the closet. She was sexy, but looked obscene, too. The black leather harness was strapped around her hips, with the blue, condom-covered anal dildo sticking out, like some kind of an alien penis. It wasn’t really that big, only about 5 inches long and about an inch in diameter at its widest point. It was kind of like a rocket nosecone. Teri was rubbing lubricant all over it as she walked toward the bed.
“But it’s going in Brad,” Ann thought. “He’s in for a surprise.” She looked at Teri again as her roommate moved towards the end of the bed. Her nipples were hard and pointed; they looked longer and larger than Ann had ever seen them.
Teri gestured at Ann – wrap yourself around him she mouthed. Ann did as she was told. She hooked her legs around Brad’s hips, pulling him deep into her. Her arms reached around and pulled him tight to her. She kissed him, pushing her tongue into his mouth.
Teri moved to the end of the bed. Following the plan, Ann had scooted herself and Brad down toward the end of the bed so that Teri would be able to reach his butt easily. Brad’s hips moved slowly back and forth, pushing his penis in and pulling it out of Ann’s grasping vagina.
“I’m so turned on,” Teri thought to herself.
Gently she reached out, her hand filled with lubricant, and reached between Brad’s buttocks. She found the tight little hole of his anus and slid a finger into it. Brad jumped.
“It’s just Teri,” Ann whispered, tightening her grasp around Brad. “Don’t stop, it feels so good.”
Brad didn’t know what to do. It felt so good to be inside Ann. She was moving with him. She was soft and warm and tight. But there was this finger inside him, inside him where only a doctor had ever been before. “Please Brad, don’t stop, I’m getting close,” Ann whispered.
Brad let his penis make the decision. He kept stroking in and out of Ann’s wonderful tight warm soft vagina. He felt Teri move close behind him, and Ann’s legs unwrapped from around his hips.
Teri looked at the tight little butt in front of her. “Ann certainly got that part right,” she thought. “He does have a nice butt. And now I’m going to deflower it.”
Teri placed the tip of the well-lubricated dildo against Brad’s anus. He flinched a little, but then continued moving in and out of Ann. His movements made the very tip of the dildo just begin to penetrate him.
Teri moved closer to Brad and leaned forward. She braced the dildo with her right hand, and then pushed forward with her hips. The blue shaft slowly penetrated the tight brown ring of Brad’s anus. She watched as it stretched to accommodate the dildo.
“Oh god,” said Brad. “What are you doing?”
“I’m making a sandwich,” said Teri. “You’re the meat. Just relax. I’m going real slowly. Tell me if it hurts too much.”
Curiously, it didn’t hurt that much, Brad thought. It wasn’t comfortable, but it wasn’t painful. He felt kind of full. “This is weird,” he thought. “I’m in Ann and her roommate all of a sudden is in me, kind of. And I’m with two women. And it’s only the second time I’ve had sex.”
Just then, Teri pushed a little harder and the last two inches of the dildo were buried completely in Brad. He felt the leather of the harness press against his buttocks, and felt Teri’s thighs against his as she moved up against him.
“Ok, let’s get a rhythm going,” said Teri. She began thrusting, her hips moving back and forth, the slim blue dildo penetrating and withdrawing, rubbing and stimulating Brad in a way he’d never experienced.
Brad resumed his movements in and out of Ann’s clasping vagina. The sensations were overwhelming. Every inch of his penis was being stimulated by Ann’ soft, warm, clutching vagina. Her warm body was pressed beneath his. His rectum was being filled repeatedly by Teri’s thrusts. He was surprised how good it felt. Teri’s hands were on his hips, helping her keep the dildo in him. Her soft thighs pressed against his.
Brad didn’t last long. The dildo in his ass rubbed against his prostate and the tightness of Ann’s vagina brought him quickly to the edge.
“I’m going to cum,” he groaned.
Teri thrust her hips more rapidly against, driving the dildo deep into him, over and over again. Brad matched her rhythm, thrusting hard into Ann. And then he was cumming, his orgasm racing through him.
“Oh god, oh god, oh god, oh god,” he repeated, his semen spurting out, only to be contained within the rubber.
Brad collapsed on top of Ann, and Teri pulled back slowly, softly withdrawing the dildo from where she had buried it in him.
“My turn,” Teri announced a few minutes later.
“What do you mean,” asked Brad.
“Go clean up, and then get back in here. We’re just starting,” Teri said.
Brad went to the bathroom, stripped off the condom, tied it in a knot, wrapped it in toilet paper and buried it in the wastebasket. He grabbed a washrag and cleaned his penis and testicles and the area around them.
In the room, Teri had unbuckled the harness from her hips, pulled the slim blue dildo from it, and replaced it with a fairly realistic penis-shaped dildo. She rolled a condom down over it and then helped Ann get into the harness. Ann was spreading her vaginal lips to embrace the raised mound at the back end of the penis. Brad walked back into the room as she nestled it into herself, positioning her clitoris so that it would rub against the dildo as she thrust..
“You’re not going to…” Brad asked, anxiously.
“No, stud, you’re not going to get it in the ass again, at least not right away,” said Teri. “It’s my turn.”
“What do you want us to do?” Ann asked, even though she was pretty sure what was going to happen.
“I want both of you in me at once,” Teri replied. “I’m going to ride Brad and you’re going to do me in the ass.”
“You’re kidding,” said Brad. Teri was every bit as wild as Ann had described, he thought, and a bit more.
“No, I’m not. And when we’re done with that I’ve got another idea. So lie down.”
Brad did as he was told. Ann got another condom from the drawer and rolled down over Brad’s once again erect penis. Teri straddled him.
“Ok, big boy, here we go,” she said.
She grasped Brad’s penis and rubbed it up and down her labia. “He’s a nice size, isn’t he?” she said to Ann.
Ann blushed. “Well, I don’t have lot to compare it with, but I like it,” she said.
“Well, look at it. You saw George. He’s a little longer, but he’s not as thick as Brad is. I bet this feels real good.”
Brad didn’t know what to say. Here was this woman, Ann’s roommate, and she was holding his penis and rubbing it’s tip up and down her slit and talking about how big he was, or wasn’t, or…he couldn’t decide. And then Teri positioned his penis at the mouth of her vagina and slowly slid down on top of him.
“Oh, yeah, this is real nice,” said Teri. “You’re nice and thick, and you’re stretching me just right.” She lifted up a little, and then slowly slid all the way down on top of him, her mons pressed tight against Brad’s pubic bone, their pubic hair mingling.
Ann watched this lewd display. She hadn’t really stared much that time she and Teri and George were together. Mostly she had kept her eyes shut, enjoying the feeling but too nervous to look. Now she stared at how Teri’s dark pink inner labia spread and clutched at Brad’s penis.
Teri leaned forward, and Brad began to suck on the nipple that dangled in front of his mouth.
“That’s nice, keep it up,” she said. “Ann, it’s your turn now. Grease me up good, and then do me nice and hard.”
Ann squeezed the tube of lubricant, depositing a generous dollop on her fingers. She applied them to Teri’s anus, pushing in first one, and then two fingers.
“Put more in,” said Teri. “And grease up that dildo real good, too.”
Ann complied. This time she inserted three fingers into Teri’s tight brown hole. Deliberately, she stroked against the wall closest to Teri’s vagina, feeling Brad’s penis.
“Oh, geez, that’s nice,” said Brad.
“Quit playing,” Teri said. “Get up here and put that thing in me”.
Ann pulled her fingers from Teri, squeezed more lube on them, and liberally anointed the dildo. When she was finished, she climbed up on the bed between Brad’s legs.
“Hurry up,” said Teri.
“Just be patient,” said Ann. “Here it comes.”
Ann scooted up a little closer to Teri and rubbed the tip of the silicon phallus around Teri’s anus. Then she centered it in the hole and slowly leaned forward, sliding the dildo into Teri’s rectum.
Brad felt the dildo sliding up along his penis. It was almost as if there were no barrier between it and him. He shuddered.
Ann moved slowly, watching Teri’s anus stretch to accommodate the invading phallus. She watched as it disappeared into her friend, and then her hips were firm against her friend’s buttocks.
“I feel so full,” said Teri. “This is really strange. Start moving.”
Brad gently thrust up into Teri as Ann slowly withdrew. They developed a gentle rhythm, moving in and out alternately.
Teri was in ecstasy. Brad was playing with her nipples and moving up into her, Ann was filling her backside. She began moving against their rhythm, stimulating every nerve. She began to pant and moan.
“Oh, oh, oh. That’s so good, unh, unh, unh, yeah, like that. unh, OH! that’s it, just like that, don’t stop, don’t stop.”
Brad had taken her right nipple into his mouth and was worrying it gently with his teeth. The sensations were tremendous. Teri was one enormous, erotic nerve. Her body began to tremble. Ann embraced her, pressing her breasts into Teri’s back, reaching around and caressing the breast Brad wasn’t tormenting.
“OH MY, OH MY, OH MY! MY PUSSY, MY ASS, MY TITTIES, MY! MY! OH! OH! OH! MY PUSSY, MY PUSSY, I’M SO CLOSE! SO CLOSE!”
Ann had never heard her roommate react so loudly before. Teri always made noise, but nothing like this.
“DO ME FASTER, DO ME FASTER, THAT’S IT, OH YEAH! OH YEAH! HERE IT COMES! HERE IT COMES! EEEAAAGGHHHHHHHHH!” Terri screamed as her orgasm ripped through her, shaking her from head to toe. Nothing had ever felt this good. Brad and Ann kept thrusting.
“It’s coming again,” Teri gasped. “Don’t stop, don’t stop!” she pleaded.
Ann and Brad did as she asked, continuing to move in and out of Teri, pushing her closer and closer to a second orgasm.
“OH MY GOD!” Teri screamed. “WAAHHHOOOOO! OH, OH, OH YEAH! OH SHIT IT’S SO GOOD, IT’S SOO GOOOOOOOOD!”
Her second orgasm came on the heels of the first. Teri trembled and shook as it raced through her, engulfing her with a pleasure she had never experienced before. She was so full, and she was being held between these two people, and her roommate was in her ass with a strap-on, and this boy across the alley Ann had just never stopped talking about was in her, and her breast was in his mouth and she just felt so warm and good and erotic and horny and relieved all at the same time.
It was fifteen minutes before Ann slowly pulled out of Teri’s ass and Teri rolled off of Brad’s now soft penis.
“That,” she said, “was tremendous. Now it’s your turn, Ann.”
“I don’t know,” said Ann. “I don’t think I could take what you just went through.”
“Well, then, I’ll tell you what. I’m going to lie down here and be lazy, since the two of you have kind of tired me out.. You get on your hands and knees, but put your crotch in front of my face. Kind of like if we were going to 69. Brad, give me some pillows.”
Brad did. Teri put the pillows under her head, raising it up so her mouth was positioned just under Ann’s genitals.
“Now Brad, put on a fresh condom.” He did so, thinking that she was going to have him do Ann doggy style.
“Ok, Brad, you lost your anal virginity tonight, now Ann gets to lose hers.”
“Teri!” Ann gasped.
“Don’t Teri! me,” Teri responded. “You’ve had fingers and dildos up there already. It’s time you had a real penis. And I’m going to suck you off while he does that.”
Brad had donned a fresh condom and had found the bottle of lubricant. He smeared some on his fingers and reached out for Ann’s anus.
“That’s right,” said Teri. “Lube her up real good. Nobody’s rectum makes its own lubricant, like a vagina, so we have to add it. The more you use the easier it will be for both of you.”
Brad gently pushed a lube-filled finger into Ann’s anus and rubbed it around. Ann moaned. Brad withdrew his finger, loaded it with more lubricant, and pushed it back insider her.
“That’s good, Brad,” said Teri. “Now grease yourself up.”
Brad poured a puddle of lubricant into his hand and stroked himself. This was quite a night. First, Ann wanting to be with him again. And then, the reality that she was setting him up so they could do it with her roommate. And Teri was as wild as Ann had told him she was.
“Ok, you know what to do,” Teri said.
Brad moved closer Ann, grasped his penis, and placed it against her anus.
“Go slow,” Ann told him.
Teri began to lick Ann.
“Oh god,” Ann moaned.
Brad began to push into her. She was so tight. The head of his penis slipped inside the ring of her sphincter.
“Wait a minute, Brad. Let me get used to it,” Ann said.
“Ok.”
Teri reached up and spread Ann’s labia open. She thrust her tongue deeply into Ann’s vagina, savoring the musky taste of Ann’s excitement.
“Go deeper now, Brad,” Ann said. “But real slowly.”
Using all of the restraint he could muster, Brad pressed forward, easing himself into Ann’s tight, hot rectum.
Teri began to concentrate on Ann’s clitoris. She circled the hard pink bud with her tongue, stimulating it unmercifully.
Brad continued to slide into Ann. Finally he was all the way in, his belly pushed hard against her buttocks, her anus stretched wide around his penis.
“That’s so nice,” muttered Ann. “Brad, pull out, slowly, but not all the way. Then slide back in. Just take it real slow.”
Brad withdrew almost as slowly as he had pushed in. The tight ring of her anus caressed every inch of his penis. Just before the head pulled out he reversed, and pushed back in to Ann’s tight little ass. Teri inserted two fingers into Ann’s vagina.
Ann began moaning steadily. “Uhh, uhh, uhhhh, uhhh, so good, so good, faster now Brad. Uhh, uhhh, uhhh.”
Brad picked up the pace. Ann’s vagina had been wonderful, and so had Teri’s. But this was a whole new level of stimulation. Ann clenched down, her anus contracting almost viselike around Brad’s penis. “Faster, Brad. Do me hard. It feels so good, so good.”
Teri continued to mouth Ann’s clitoris, sucking it deep into her mouth, flicking the pink pearl of pleasure with her tongue. Ann began to tremble. Brad’s moans joined hers.
Teri licked the index finger of her other hand, reached around and gently inserted it in Brad’s anus, probing for his prostate. She found it, and gently rubbed it.
That pushed Brad over the edge. He thrust deeply into Ann and came, shouting out – “Oh god, yes, that’s it, that’s it.”
Ann felt that last hard thrust just as Teri started flicking her clitoris more quickly. Her orgasm built quickly and washed through her, just as Brad started to relax a bit.
“That’s it, just like that! I’m almost there! OH! OH! OH! OH! IM CUMMING, I’M CUMMMMMMINNNNNNGGGGG” she cried. Her body shook and she felt a gush of liquid flow from her vagina, soaking Teri’s face. It was wonderful and exciting and then relaxing and comforting and she really couldn’t figure out where all that liquid came from but she knew it wasn’t pee. Teri was still licking her, and Brad held himself firmly inside her as she trembled with the pleasure racing through her body.
Brad slowly withdrew from Ann and then headed for the bathroom to clean up. When he came back a few minutes later Ann and Teri were kissing gently. They looked up and beckoned him into the bed with them. He joined them and they wrapped themselves around each other, joining in an awkward three-way kiss.
When they broke apart Ann was the first to speak.
“That was wonderful. Thank you both so much. I want to do it all over again. I want to lie here tonight with you and sleep in each other’s arms. And tomorrow I want to do what we did with you, Teri, and more…”
Teri and Brad embraced Ann again. They fell asleep entangled in each other. The next three days, until their parents returned, were a long orgy of exploration and orgasm.