Jen was still lying on top of me; her thighs still straddling my head. I caressed her firm round ass, and kissed her inner thighs. The kisses were affectionate, not sexual.
I was feeling and unexpected affection for both Jen and Demarcus at the moment. It dawned on me that prior to last weekend, the only person with whom I had climaxed was Tom. I had limited sexual experience in high school. Before I met Tom in college, I dated a couple of boys, but I never achieved an orgasm with any of the guys I was with. So Jen and Demarcus now belonged to a very exclusion club of three people who had made me cum.
I learned something about my psyche’ that surprised me a bit. I had no idea that the intimacy of sharing an orgasm with someone would evoke such a feeling of affection and closeness within me. Despite the fact that I agreed to these extramarital experiments with the expectation that it was just physical sex without any emotional entanglement, I was feeling a deep emotional connection with Jen and her husband at that moment; and it felt good.
I wondered, just for an instant, would I have fallen so deeply in love with Tom if he had not made me climax regularly when we first started dating back at the University of Colorado more than twenty three years ago? It was an interesting, albeit irrelevant question. I did fall deeply in love with my husband, and I even as I lay there, gently kissing Jen’s inner thighs, savoring the sweet, subtle scent of her vagina and caressing her firm buttocks, I knew I belonged to Tom. I was his, and he was mine.
With my arms wrapped under and around Jen, and my hands on her buttocks, I separated her cheeks slightly and looked at her shaven vagina. The lips of her labia opened slightly. Her pussy glistened from a combination of her secretions and my saliva. The deep pink color of her inner lips appealed to me.
“Jen, I did not ever think I would be in a position to say this to another woman, but your pussy is very pretty. And I love your scent. God you are sexy.”
Jen raised her head slightly off my thigh and looked back over her shoulder, “Well, thank you. No one has ever said that to me before. And I love your pussy as well.”
She then moved slightly and buried her face against my vulva, kissing me several times, and flicking her tongue against my clitoris one last time. I moaned appreciatively.
I lay my head back on the pillow, hugged her waist and smiled inwardly, grateful that Tom and I had the confidence in our love, and in our relationship, that allowed us to explore these wonderful intimacies with our best friends. I felt loved, content and well satisfied as I lay there, cuddling with Jen as Tom and Demarcus watched.
I glanced up to see both men changing their positions. Demarcus and Tom both had raging erections, and they needed a place to put them.
I wanted to savor my first lesbian experience a while longer. I wanted to cuddle and caress Jen in post-orgasmic bliss, but I realized that was not going to happen. Demarcus and Tom needed to fuck someone, now.
Jen rolled off of me, onto her back and said, “I think our men are looking for a warm, wet place to stick their boners. Got any suggestions?”
“Oh my, those are impressive erections they are sporting. I have just the place for your husband’s big black cock.”
Then I remembered, Jen’s fantasy was to experience two penises at the same time, one in the front and one in the back.
“Jen?”
“Yes, Christine? What?” she responded.
“I think you should live out your fantasy. I’d love to help and watch.”
I wanted to give this to Jen, to help her achieve this experience. Jen knew immediately that I was referring to her fantasy of being double penetrated by Tom and Demarcus.
“Oh my. I don’t know…you think I should try that? Both at the same time?”
“Definitely. I want to watch you take both of them. Guys, are you up for double teaming my friend here?” I asked, rhetorically.
Demarcus looked to Tom, “You want to try this with Jen?”
Tom smiled and nodded, “Nothing I’d rather do.”
Jen reached over and took my hand in hers. Squeezing it tightly, she said nervously, “Christine, I want you to be right here with me while I try to do this. Don’t leave me, okay. I’m a little nervous about this.”
“Jen, I’m not going anywhere. I want to be a part of this. I want to experience this with you, vicariously,” I assured her. My voice was quaking slightly from my excitement.
Tom interrupted, “Let’s move this party to the bedroom, where we can be more comfortable. Jen, did you bring any lubricant?”
Jen let out a little giggle, “Yes, I did. But not because I thought this was going to happen. I brought it in case you wanted to take me back there again. I never imagined that I would try to take both of you at the same time.”
She got up to get her purse. She quickly produced a purple and white tube of Walgreen’s generic personal lubricant. I was amused that she bought the cheaper, generic brand. I would not have predicted that about her.
Demarcus took my hand, and turning to Tom, he said, “Lead the way my good man.”
Tom placed his hand on Jen’s butt and guided her to our bedroom.
Once in our bedroom, he quickly grabbed the comforter and blankets from our king sized bed and pulled them off, tossing them in a pile in the corner, beside his dresser.
Demarcus turned to me, leaned down and kissed me deeply. I opened my mouth to accept his probing tongue as he fondled my left breast. I reached down wrapped my fingers around his very thick, black penis, and stroked it several times. I was still amazed at how thick and heavy it felt in my tiny hand.
Demarcus broke off the kiss and said, “Are you okay with Tom and I doing this with Jen? You won’t feel too left out, will you?”
“Oh god, no. Not at all. I want you guys to do this to her. I want to watch.”
I stroked his large erection and leaned over to kiss the large, purple-black glans, before adding, “Just save some of this for me for later, okay?”
“Christine, I promise you, I will take care of you really well after we make Jen’s fantasy a reality,” Demarcus assured me. “So you stay real close.”
“Oh I plan to do just that. In fact, I may use my vibrator while I watch you double team her.”
“That’s exactly what you should do. Fuck, that would be so hot to see you make yourself cum while Tom and I give Jen all the dick she can handle.”
I went over to the nightstand and retrieved my favorite toy, an eight inch long, one and a half inch thick, bright red phallic shaped vibrator. It was made of a supple, jelly-like material that felt quite realistic and retained heat nicely. It really did feel like a real penis once it was inside me.
“So Jen, how do you want us to do this?” Tom asked.
“Oh, I feel so wickedly naughty even thinking about this,” Jen giggled playfully. “Demarcus, lie on your back. Christine, would you make sure he is good and hard? I want you to make sure both men are hard enough to do this, okay?”
I nodded and said nothing. I liked having a role here, rather than simply being a spectator.
Demarcus laid down as instructed. I immediately knelt next to him and took his rigid cock into my tiny hand. Although I had ample experience with his penis a week ago, I was still in awe its size and girth. I allowed my fingers to encircle the dark shaft. I could barely get my fingers all the way around it. I was still intrigued with the coloring as well as the size of this huge cock. It was not really black, but a deep, deep shade of purple. It was a shade of purple that I had not seen before, and it was strangely beautiful to me. The well defined glans was slightly lighter in color than the shaft. It looked almost like a deep shade of pinkish-purple.
I stroked it up and down a few times before leaning forward and kissing the head, which was already moist and slippery from the secretion of pre-ejaculate semen that was seeping out Demarcus’s urethra with his excitement.
Demarcus was already completely erect. He really did not need an help from me getting had. But still, I wanted to fulfill my assigned role. Dutifully, I opened my mouth taking the sensitive glans into my mouth.
I swirled my tongue around the head several times before removing the cock from my mouth and pronouncing, “Jen, he is more than ready for you. Are you ready for him?”
I continued to hold and stroke his rigid tool as Jen climbed astride him, and said, “Christine, I am so wet from when you were kissing on me down there earlier, I think he’ll slide right in. Would you hold his cock and kiss me while I mount my husband?”
Her words, sent a pulse of excitement through my loins. I held Demarcus’s cock straight up as Jen positioned herself so that the thick head was at her opening. She reached over and placed her fingers under my chin, drawing me to her face.
“Kiss me while he enters me,” she said, almost pleading as she began to lower herself down.
I kissed her, probing mouth with my tongue as she moved up and down, grimacing slightly as the large erection wedged deeper inside her. When I felt her thighs contacting my fist, I knew she had the majority of his cock inside her, and I released my hold on it.
I caressed her breasts and face as we necked, until Demarcus demanded her full attention.
Demarcus pulled Jen forward, holding her so that her large breasts were pressed against his massive chest. He started arching his hips, slowly fucking her. I looked behind her and could see the thick, black shaft slowly sliding in and out of her stretched pussy.
She clearly accommodated his large cock easier than I could. But she had a lot more practice doing so, right?
After thirty or forty seconds, Jen asked, “Christine, would you prepare my bottom for Tom’s cock? And then get him ready? Use lots of K-Y.”
I understood what she was asking. I grabbed the tube of lubricant and placed a large glob on my right middle finger and index finger. I then climbed back on the bed. Using my left hand, I spread her butt cheeks apart. I saw her tight, pink sphincter, puckered closed. I took my index finger and pressed the tip against her anus. Slowly, about a half an inch slid inside.
I was amazed at how tight she was back there. It was hard to imagine that Tom had fucked her back there last Saturday morning. Carefully, I pressed deeper. She moaned as my finger slid past the first knuckle, stopping at the second knuckle, coating her tight backside with lubricating gel. I withdrew my finger and pushed it in again; this time I twirled it around slightly trying to relax her tight anus.
Jen arched her back slightly, and moaned as she pushed her bottom backwards.
“Oh, be careful…shit…wait…” Jen begged.
“Just relax and push back, Jen. You can do this,” I reassured her.
Soon, I had worked both my index finger and my middle finger all the way inside her ass. With the tips of my fingers pointing downward, towards her navel, I could feel the shaft of Demarcus’s thick erection through the thin membrane separating her rectum from her vagina. I massaged his cock gently with my finger tips from inside her ass.
“Can you feel that? Can you feel my fingers in her ass?” I asked Demarcus.
“Oh, fuck yeah. You need to stop doing that. You’re going to make me cum if you keep that up. Shit, Christine, you are one sexy bitch.”
I suddenly felt very powerful, knowing that I could make my large, handsome, black lover lose it by massaging his cock from inside his wife’s tight ass. It was a unique feeling to have my two fingers inside Jen’s rectum, feeling the large shaft of her husband’s cock in her vagina.
I looked over my shoulder at my husband. His erection was straining towards the ceiling, rigid as stone.
As I withdrew my fingers from my best friends backside, I told Tom, “Baby, that is so freaky the way I could feel his cock from her ass. I’ll bet you’re going to feel it too when you fuck her back there.”
Tom’s cock arched up in response to my words. I then held Jen’s butt cheeks apart, and instructed Tom, “Okay, baby, you’re up. Come here and give it to her. Give her the second dick. She wants two.”
Jen buried her face into Demarcus’s massive chest and moaned in preparation for her penetration. I could see Demarcus hugging her tightly holding her in place. Tom positioned himself behind her, kneeling. I watched my husband guide the pink head of his erection against Jen’s tight, but well lubricated bum.
Tom pushed forward ever so slowly. I watched in amazement as the mushroom shaped glans started to wedge its way inside Jen’s upturned ass.
Jen started to whimper, and cried out, “Oh god, hold still…shit, you’re are too big…don’t push…wait…oh fuck, it hurts.”
Tom had not gotten his glans past her opening when he was forced to stop. The ridge of his glans was just outside her anus, throbbing with excitement. I worried he might climax too quickly, but he had amazing control.
I placed my hand on Tom’s abdomen, signaling for him to remain still. At that moment, I felt very much in control. I felt like the director of a porn movie. I was giving the actors the signals what to do and when. I loved this feeling of power.
“Jen, are you okay, girl?” I asked.
“Uh huh, I think so. Oh fuck, Christine, he’s so big,” she moaned into Demarcus’s chest. I watched her fingers clawing at the sheets as she attempted to endure the pain of entry.
When Jen said the words ‘he’s too big’, I saw Tom’s cock swell slightly and arch up, stretching her tight anus more.
“Oh, shit…don’t move,” she begged.
There was something incredibly sexy and arousing about watching my best friend be impaled this way. Her whimpering and cries of pleasure and pain had my vagina literally flowing now.
Tom remained motionless, trying hard not to pulse his erection.
“Jen, when you are ready, I want you to push back a little on Tom. Tom, let Jen push you in. Don’t move,” I instructed.
I wanted to touch myself. I knew I could cum in an instant. But I had a job to do. I needed to get Tom’s cock into Jen’s bottom so that my husband and her husband could give her a proper fucking; a fucking she deserved.
After ten or fifteen seconds, Jen grimaced and pushed back. She grunted and moaned loudly. I watched in awe as the ridge of the glans slowly disappeared into her ass. She took about an inch before needing to stop and regroup.
I knew that it would take time and patience, but Jen was highly motivated to do this. I knew she was going to take all of Tom’s boner in her backside regardless of the pain of entry. She wanted this. Shen needed to do this, for herself, for her husband and for Tom.
Again, after ten or fifteen seconds, she grimaced again, and pushed back some more. She now had about half of Tom’s hard cock in her backside.
After a moment or two, the pain seemed to subside and Jen forced a little more of my husband’s cock into her bottom. And every time she would push back, she would tell Tom to be still and that it hurt; but she seemed to like the fact that it hurt a little bit. She was determined to take him back there no matter how bad it hurt.
Tom placed his hands on her hips and pulled her backwards, encouraging her to take the last two and a half or three inches of his cock.
I watched as she grasped the sheet into her hands, squeezing tightly, and whimpering incoherent sounds. Jen pushed herself all the way back until her buttocks was pressed against Tom’s thighs. I assume she could feel his balls pressing against her as well.
“Everyone, stay still,” she commanded.
Demarcus asked, “Are you okay? How do you feel?”
Jen raised her head to look into his face and replied, “I think I’m okay. But your wife is very, very full. I am so full of cock, baby. Oh fuck. I love you. Thank you for letting me do this. I did it too, didn’t I? I took you both.”
“I love you too, baby. And yes, you took us. But we are not done with you yet, baby; not by a long shot.”
Demarcus started rocking his hips, slowly fucking her pussy. Tom took this as his queue to move in and out. But Jen cried out in pain, “Oh fuck, Tom…stay still…oh fuck, it hurts…”
Tom stopped pushing in and pulling out. Instead he began flexing his cock in her ass while Demarcus fucked her. Every time he flexed his penis, she would stiffen slightly and moan. Her moans conveyed a combination of pain and pleasure. Clearly, it hurt somewhat, but she certainly seemed to like it, a lot.
I was so turned on myself. I wanted to cum with them. While Tom continued to make her whimper and moan, Demarcus continued to fuck her.
I grabbed my large red vibrator. I rotated the base, causing it to buzz to life. I took a pillow and folded it over on to itself. I placed the folded pillow next to Jen and using the pillow to hold the base of the vibrator in place, I straddled the pillow and inserted the vibrator inside me.
In this position, I could fuck the big red dildo against the pillow, riding it like I would ride a man from on top, but my hands were free. I began humping the buzzing phallus as I caressed Jen, alternately rubbing her back and buttocks, and squeezing her breasts which were flattened against Demarcus’s chest.
Jen’s arousal was building. Her anus seemed to have relaxed somewhat because she was now rocking her hips and forcing Tom’s cock to slide in and out of her an inch or two.
“Can you feel both cocks? Can you feel the one in your ass? Can you feel that big black dick in your cunt?” I hissed as my arousal grew. I was fucking my dildo in rhythm to Jen fucking her men.
“Oh god, yeah. I am so full of dick,” Jen cried out. “Oh fuck me.”
“Demarcus can you feel Tom’s cock in your wife’s ass?”
Demarcus just grunted and started to fuck her harder.
Jen started crying out, “Oh fuck, I’m going to cum…shit…just like that…just like that…don’t stop…just like that…oh fuck my ass…oh shit…oh fuck my ass…don’t stop…oh fuck…here it comes.”
And a series of powerful convulsions shook through her body. Tom was now pulling all the way out and pounding is cock into her ass.
Jen screeched, “Shit, cum with me… cum in my ass… cum in my cunt…oh fuck, please cum in me.”
Her words pushed me over the edge. I screamed , “Oh, oh, oh, I cumming.” I pressed myself down on the vibrator, forcing the head deep into my vagina, pressing against my g-spot.
My eyes rolled back in my head, but I could see Tom stiffen and press his cock deep into Jen’s ass. I could tell by the way my husband quivered stiffly, he was ejaculating in her backside.
Demarcus let out a series of loud grunts tell, me that he was filling her vagina with his sperm.
I collapsed forward, allowing the vibrator to slip from my pussy. I fell on top of Jen and lay there, rubbing her back, trying to regain my senses.
I did not have the strength to even turn off the vibrator at hat moment. It lay there, buzzing loudly, on the side of the bed.
The men remained coupled inside Jen for several minutes. Finally, Tom began to withdraw.
Jen’s reaction surprised me yet again. She cried out, “Oooo, ouch, ouchie, ouch, go slow.”
Apparently, even after climaxing, withdrawing from her rectum was somewhat painful.
Once Tom withdrew completely, Jen kissed Demarcus and said, “I love you. Thank you again. Tom and I are going to take a shower, okay? We need to get cleaned up. Would you keep Christine company? I think you promised her some attention earlier.”
Jen stood up, walked over to me, kissed me affectionately on the lips, and said, “Thank you, too. And by the way, I had Demarcus take a Levitra pill earlier. He’ll stay hard all night for you. I promise.”
I hugged her, pressing our naked breasts together and replied, “Thank you. You know I love you, girl.”
Jen smiled and said, “I know you do. And I love the both of you as well. I really do.”
She then turned to Tom and said, “Come on lover boy, let’s get that shower.”
I chimed in, motioning to my husband’s cock, I said, “Wash that thing really well.”
“Oh I will. By the way, your husband is a very, very sexy man.” Then looking at Demarcus, she said, “Do this lady some good.”
I heard the shower running in the bathroom, as I laid next to Demarcus. His penis was long, firm and thick, but not as rigid as it had been. I rested my head on his chest, and caressed his nipples.
“You really don’t need to ‘do me any good’ right now. I am perfectly fine. I have already cum twice tonight.”
He laughed, “No a deal is a deal. And we have all night. But I would like to cuddle and rest for a minute.”
“Me too. I’d like to let Tom watch you fuck me. After all, that was his fantasy. And I want to do that for him.” I thought for a moment, and continued, “Why don’t you and Jen spend the night. I’ll even fix us breakfast in the morning.”
“Will you stay naked until we leave?”
“Oh, you nasty boy! I guess I did tell you that was my fantasy. Okay, you can have me naked any time it’s just the four of us here.”
“Any time?”
“Absolutely, any time.”
“Girl, you are going to be naked a lot then,” he laughed.
