16 October 2009

My First Threeway... or how I gave up my virginity at 16

It was summer. I’d be 17 in October and it was my first real holiday away from home without my parents. I was visiting with Sinéad (no, not that Sinéad), my aunt, in her very nice apartment in Chicago. Sinéad was 28 then, single, working, and not at home much. We would spend most of our together time on weekends, but I was pretty much left to my own devices during the week. I’d visited before from Ireland, but never alone or to stay for the whole summer.

Cathy, who was just 19 and a friend I had recently met and hit it off so very well, was giving a small dinner party for her husband, Derek. They were still newly weds and it was his birthday. He was just 21. Cathy was a few inches shorter than me, maybe about 10 to 15 pounds heavier, mostly in the breasts, blonde with a shorter cut, big blue eyes and a beautiful smile. Derek was 6 foot 2 inches tall, about 185 pounds, wavy dark hair that hung just to his shoulders, athletic, but not a work out junkie, dark eyes and always looked like he was a day behind in shaving.

It was hot in Chicago that day and the window unit air conditioner wasn't working very well in their apartment. So Cathy decided to get a bucket of chicken, a bottle of wine, and have us eat on the roof of the building. I had also brought a bottle of wine for dinner – you can't go to a dinner party and not bring wine. Cathy and I had sunbathed up there a few times, mostly nude, and even masturbated there together a couple of times. We were a few feet apart, but I still got to watch her as she orgasmed, and she, in turn, got to watch me. That was my first time masturbating with anyone else. I'd never thought about having sex with a woman before, but us masturbating together made me start. Even to this day, I sometimes think of those times with Cathy on the roof when I masturbate.

Anyway, so we’re all up on the roof, watching the sun set, just Cathy, Derek and me. We ate the chicken and drank the first bottle of wine and were just sitting there chatting about the day, nothing serious. Derek was dressed in an unbuttoned Hawaiian shirt, jeans and flip-flops. Cathy was wearing a pair of bib overalls that she had cut down to shorts, a bikini top and, also, flip-flops. I had on a simple halter top, jeans shorts and my favourite trainers.

After a while, Derek pulled out a couple of joints from his shirt pocket that a friend of his had given him for his birthday. Cathy took one, lit it, took a long drag and then gave it to me. I had smoked marijuana before, so I took a good, long drag and prepared to pass it to Derek, but he had already lit the other one. “You two share that one,” he coughed as he exhaled a thick cloud of smoke. So Cathy and I smoked about two thirds of the joint we had, while Derek smoked almost all of his.

By this time we were all giggling and having fun when Cathy said “We need some music. If we keep the bedroom window and kitchen window open, there should be enough of a breeze…”

We all agreed it was an excellent idea and headed down to their apartment on the top floor of the building. I made sure to pick up any rubbish and leftovers while Cathy made sure she got the second bottle of wine and the glasses. By the time she and I got to their apartment, Derek had already opened the suggested windows, lit several candles all around the apartment, and was preparing the CD changer for some party music.

The music came on and Cathy started dancing. Derek just stood there watching her for a little while, with that “that’s my wife” smile on his face. I watched her a bit, too. She was really having fun. And I could tell by the sizable bulge in his pants, so was Derek.The next song was slow, so Cathy grabbed Derek and they danced together a little. She suggested that I open the other bottle of wine. By the time that song was over, I had the bottle opened and a glass poured for each of us. When I handed Cathy her glass, she kissed me. It sent sparks all the way down to my clit and right back up to my nipples. I felt so very good.

We all kicked off our shoes and sat on the sofa, drinking the wine, listening a little to the music and talking. We were all telling stories about ourselves and our different friends growing up and laughing and having a good time. It was a party.

After a while, Cathy got up from the sofa. “I need to pee and then I need another glass of wine. Anybody else?”Derek and I both said “Yes” at about the same time. We all giggled. Cathy went to the bathroom first, then me, and Derek waited for last. When I got out of the bathroom, I noticed a few candles had gone out, but there was still a nice glow to the room.

When Derek came out of the bathroom, Cathy and I were sitting on the sofa, but hadn’t really left much room for Derek to sit there, so he sat in the chair. But before he could completely sit down, Cathy says “I’m kind of bored with the music, wanna watch TV? Is there any pot left?”

Derek answered the second question first. “Yea, I’ve got one more joint left, it’s in the bedroom. I’ll go get it. You want to pick out a movie?”

Cathy smiled at Derek and then turned and winked at me. I had no idea what the wink was for, except maybe about the other joint. I smiled. Once Derek had left the room, Cathy reached under the sofa and pulled out a small wrapped package.

“You said no presents!” I loudly whispered at Cathy, looking quickly towards the bedroom. I hadn’t gotten Derek a present under strict instructions from Cathy. She said that all he wanted was a “nice, quiet evening at home.”

“I know,” she says with a kiss on my left cheek, “I know,” a kiss on my right cheek, “I know,” a quick kiss on my mouth. “And that still stands. This is just a little extra. Besides, he’s a man. A man can’t have a birthday without some type of present.”

Derek returned to the room, handed the unlit joint to Cathy, and walked over to turn off the stereo and turn on the TV and DVD player. Cathy lit the joint and handed it to Derek.

“Oh, thanks,” he grinned and took a drag. He smiled again and exhaled “Did you pick out a movie?”

Derek handed me the joint while Cathy held up the wrapped package. “Well, sort of. Here, open this!”

“I thought we agreed 'No Presents’!” Derek mildly scolded. He turned to me “Did you know about this?”

I shook my head, exhaled and handed him the joint. “Not a thing,” I coughed. “She just pulled it out a second ago.”

He took another drag and Cathy said “Trust me, Baby. You’ve been wanting this present for a while.”

Derek passed the joint to Cathy and started to open the package. As soon as he could see inside the wrapping, he peeked and smiled a huge smile. “You didn’t!” he beamed. He quickly shred the remaining paper on the package and held up his new prize. It was a DVD. Not only that, it was porn. Cool. I’d never seen a porn movie before and I was in the right frame of mind to see one now.

“This is great!” he beamed. “You wanna watch this now?”

“If you want…” she smiled, and then looked at me. I was smiling, too. “Sure!” she finished. “Let’s see it!”

I was a bit too stoned to go back to my aunt’s apartment two floors below and I was extremely comfortable where I was, and with Cathy and Derek. Besides, watching a porn movie wasn’t going to hurt me. And if I got too turned on from watching the movie, what the hell, I’d masturbate. Cathy and I had already crossed that bridge. So what if Derek sees?

We once again got comfortable on the sofa, me at one end, Cathy at the other and Derek on the floor between her legs, all facing the TV. I looked over at Cathy as I passed her the end of the joint and noticed that she had removed the bikini top she’d been wearing. I thought back and couldn’t remember her actually taking it off, so she must have done it when she went to the bathroom.

Derek pointed the remote at the TV. The DVD started playing and immediately started showing graphic sex scenes related to phone sex lines. I must’ve looked like I was in shock, my eyes as wide as they could get. I couldn’t wait for the actual movie. I looked over and Cathy already had her hand under the overalls massaging her breast. Derek quickly changed the setting and started the actual movie which received some protest from Cathy, “Aw, c’mon, Baby! I love that part! The girls are always so überhappy to have the guys cum on their faces.”

“I know, just like you,” Derek smiled and then bit Cathy on the inside of her thigh, which made her squeal and giggle. “We can watch that part later. Believe it or not, I’d like to see the movie.”

Cathy leaned over and kissed her husband. “I love watching porn with you,” she cooed and kissed him again. “Happy birthday!” As she leaned back on the sofa, Cathy unhooked the clasps holding the bib of her overalls, leaving her large and lovely breasts exposed. I don’t know and didn’t care if she saw me lick my lips just then.

The movie itself started. Straight away there was a large boat where people were partying, a lot of female nudity, some dialog, but even 10 minutes into it, there was no sex. I was led to believe that a porn film was nothing but sex. Cathy motioned for me to come closer, so I leaned towards her and she whispered “Are you ok with this?”

“The video, or you sitting here topless?” I asked in the same whisper.

“Well, both, I guess,” she whispered back.

As I was about to answer, a very beautiful nude woman on the screen helped a stunningly handsome man out of his pants in full view of everybody else on the boat. The camera zoomed in on his erect penis. The camera pulled back and showed her stroking the penis with her hand. The penis didn’t look overly large, maybe half again as long as the width of her hand. I was mesmerized. After a few moments of stroking, the woman took the penis into her mouth.

My fanny was already wet and my nipples were rock hard from the combination of the wine, the marijuana, the anticipation of the movie and very certain masturbation, possibly, and suddenly very hopefully, in front of Cathy and Derek. I was still leaning towards Cathy when I just said “Wow.”

Cathy whispered in my ear “Derek loves it when I do that. And so do I…” She cupped her left breast and pinched the nipple. I heard her softly moan.

The on screen oral sex lasted a few more moments when another equally beautiful woman joined in. They both took turns with the penis in their mouths, but they also kissed and fondled each other. I was still leaning towards Cathy, watching in rapt awe as the two beautiful women continued to orally please the man on the screen.

I suddenly felt a hand on my knee. Cathy was still cupping her breast and her other hand had disappeared under the bottom half of her overalls. I looked down and saw that it was Derek’s hand lightly stroking my knee. I don’t know if Derek thought it was Cathy’s knee or mine, but I didn’t protest. Instead, I unbuttoned and unzipped my shorts and slowly inched my hand under until I touched my pubes. I wasn’t wearing any knickers.

Just then, the man on the screen ejaculated! Both women had their mouths wide open, tongues licking the air for some of his sperm, but his sperm was landing on their faces and on their breasts. I heard Cathy moan again and Derek’s hand was still caressing my knee. The man fell out of the picture, but the women kissed and licked and sucked the sperm from each other’s face and breasts. One woman was also masturbating herself while the other was kissing her hard. My fingers found their way to my clit. I barely touched myself there and felt a shock wave throughout my entire body. It was my turn to moan.

The woman on screen who had been masturbating now had her face between the other woman’s legs. I was amazed at how beautiful the woman’s fanny was. I touched myself ever so lightly again, sending another shock wave through my body. Derek was still glued to the TV screen. I leaned forward a little more and took Cathy’s nipple into my mouth. I remembered her telling me during one of our rooftop masturbation sessions how much she loved that feeling when Derek would lick and suck her nipple while she masturbated. She was probably trying to get me to do it then, but I didn’t pick up on it at the time. Too bad. I cupped her breast and sucked a little harder and I heard her whisper “Yes.”

Cathy let go of her own breast and stroked my back between the ties of my halter top. Her soft hand on my naked skin as I suckled her sent even more shock waves through me. I felt her untie the strings behind my neck and I moaned my approval. I felt my top come lose from my neck and I moaned again, never letting go of Cathy’s nipple. Cathy tried to reach under my top touch my breasts. I wasn’t quite ready for that, so I softly blocked her. She reached back up and untied the bottom strings to my top. That is what I wanted. I felt my top fall free. I continued to suck her nipple as I felt her hand stroking my back from my neck all the way down, just inside my shorts. Her touch was gentle and I shifted a bit to allow her more access to my behind.

I could feel Cathy’s hand slipping back behind me under my shorts, down past my anus to my very, very wet fanny. Her hand gently rubbed my outer lips, spreading my wetness on me, adding pressure and just the right movement to my already sensitive clit. She just barely slipped a finger inside me. I could feel my knees start to buckle, but I didn’t want her to stop – ever. She pulled her hand out and sucked her fingers into her mouth.

I sat back up and shifted on the sofa to my knees facing Cathy. I could see Derek still on the floor facing the TV, lightly stroking his hard penis. Cathy was looking at me, smiling at me as I cupped both of my breasts and pinched my very hard nipples.

I leaned forward again, but this time I kissed Cathy on the mouth. She cupped my breasts and the flood between my legs grew larger and larger. Cathy whispered in my ear “What do you want to do?”

“Everything!” I said aloud without any hesitation. “I want to do it with you, I want to see you and Derek do it, I want to feel him inside me, too, if it’s ok with you…” I was so very turned on, so very horny, I was almost shaking and close to crying.

By now, Derek had stood up and both he and his erection were facing Cathy and me. Cathy looked at Derek, then me, then back at Derek and smiled. She gently pushed him a couple of steps back so she could take off her overalls. She wasn't wearing knickerss either. Derek's shirt was off on his way standing up and Cathy helped him out of his pants once she was out of hers. She started stroking his penis the same as the woman in the video. I stood up and quickly pushed my shorts to the floor.

"Wow, Cathy," said Derek. "Look at Siobhán! She's a natural red head. So beautiful!"

"I know," Cathy smiled back. "We've been nude together several times already." She winked at me, then looked back up at Derek. "I can't wait to taste her pussy."

It felt so good to be nude there with Cathy and Derek. I felt completely safe, uninhibited, and ready and willing to do anything sexual with either, and hopefully both of them. I stood there, transfixed, watching as Cathy took Derek's penis into her mouth. I fell back onto the sofa, legs spread, wet to my knees. I started masturbating while watching Derek's penis go slowly into Cathy's mouth and then slowly recede.

I wanted to join in like on the video, but I was too excited just watching. Derek was very excited, too. He kept looking down at Cathy, then at me, watching them and masturbating, then back at Cathy.

"You keep that up, baby, and I'll be cumming soon... very soon..." His voice trailed off a little.

Cathy took Derek's penis out of her mouth, but continued stroking it right in front of her face. "Yes! I want you to cum! I want you to cum on my tits for me – and for Siobhán!" She started stroking his penis faster.

I knew he was very close, so I stood up behind him, wrapped my arms around him and started circling his erect nipples with my fingers. I knew that would help him, plus at that angle, I could see him cum all over Cathy.

Just as I lightly bit his shoulder, he exploded all over Cathy's breasts! Oh, how incredibly lovely! I knew Derek enjoyed it by how much his entire body was shaking as he squirted and squirted and squirted his sperm all over Cathy's beautiful breasts. Cathy took him back into her mouth, getting the last of his sperm down her throat.

While Derek was still in Cathy’s mouth, before he could completely move out of the way, I knelt down between Cathy’s legs and gave her neatly trimmed fanny a quick lick. I’d tasted myself on my fingers before, and liked it, so there couldn’t be much difference with her. I ran my tongue from her clit to her left nipple in one long unbroken lick. I tasted his sperm on her and started to lick and suck even more.

Derek fell onto the sofa where I had been. I rubbed my hand in the sperm on Cathy’s right breast and put my hand to her mouth. She greedily licked and sucked my hand while I continued licking and sucking the sperm off her breasts. I loved the taste and couldn’t wait to get more. I ran my other hand down to Cathy’s fanny. She was soaking wet! I masturbated her like I like to be masturbated. She started to moan and buck under me. I so wanted to give her an orgasm! Her moaning increased and her arms locked around my back. I knew she was close to orgasm but I wanted to eat her fanny when she came, so I quickly dove back down to her fanny and started licking.

Cathy grabbed the back of my head and screamed as she came all over my face! She wasn’t a squirter, but her juices were a lot! She quickly pulled me up to her and she started kissing me. “I’m so glad you’re my first woman,” she managed between kisses. Cathy had tears in her eyes but she was smiling the biggest smile.

“I’ve never before, either!” I was laughing, too. “But I could kiss you all night.”

We continued to lay there, Cathy and I, kissing and fondling, and I was still getting hornier and hornier. I whispered in her ear “Please…”

Cathy turned me over, kissing my mouth and face and neck. She moved slowly to my breasts and started to gently lick and suck my rock hard nipples. The instant I felt her mouth on my nipple, all I wanted was for her to get between my legs! I’d had enough foreplay and really wanted her to eat my fanny! She lingered, though, making the wait so sweetly unbearable. I tried to get my own hand there, but she started to grind her belly into me, blocking me and causing a rubbing over my clit. That only made me want her more, but I couldn’t do much more than moan “please… oh, please…”, I was so turned on.

I turned and saw Derek sitting in the chair next to the sofa, lightly stroking his penis, watching his lovely wife and I make love on their sofa. I had completely forgotten about him. Cathy and I together had obviously woken his penis back up. With as much as he came earlier, I thought for sure he was out for the night. Just as I reached out for him, Cathy’s mouth reached my fanny.

I don’t know how loud I screamed, but I know I did. Cathy’s warm mouth and tongue, once on my fanny, sent me over the edge so very quickly, I didn’t have time to breathe. I grabbed the sofa with both hands and I shook and quivered and orgasmed like never before! I almost fell off of the sofa! I pulled her to me and it was my turn to kiss and laugh and cry.

After a few moments, I sat up on the sofa, still breathing heavy and still kissing on Cathy. “After I have a quick glass of water,” I breathed, “and maybe another hit or two off that last joint,” I smiled lovingly at Cathy “I want your husband to fuck me from behind while I get another face full of your beautiful fanny.”

Derek quickly got up and returned with 3 glasses of water and half a joint. I lit it, took a big hit, and passed it to Cathy. “Have you had a good birthday so far?” I coughed towards Derek. “You are aware that it’s not anywhere near over yet…” I grabbed his penis as he stood in front of Cathy. I gently pulled him to me and took him in my mouth. I wanted to taste his sperm again in my mouth, I wanted him to cum in my mouth, but I’d have to wait. My virgin fanny wanted him first.

I released his penis from my mouth, but continued to stroke it. I looked at Cathy. Both of her hands were between her legs. “What are you waiting for? I want to see you two fuck as much as you want to,” she said, still working her fannyy.

I smiled, stood up and bent over, my face towards Cathy. Derek moved in behind me and, because I was so wet and so turned on, easily entered me to the hilt! I was sopping wet, but he was as hard as steel. My fanny tightly closed around him, he grabbed my hips and started to slowly fuck me, sending wave after wave of pleasure through me. The pain of his initial insertion was gone so verty quickly, and he settled into a nice rhythm. I reached over to Cathy and had her slide to me. Once close enough, I buried my face in her wet fanny.

Derek’s rhythm was perfect to give me tiny little orgasms, and between moans of pure joy, still allowed me to eat Cathy’s beautiful fanny. Though this was my very first threesome, my very first lesbian experience, my very first sexual experience at all, I was going at it like I’d been doing it all of my life. I never wanted it to end.

“Derek, please tell me when you’re getting close,” I said into Cathy’s fanny. When I realized he hadn’t heard me, I pushed myself up and said it again and added “I want you in my mouth.”

Derek grabbed my hips tighter and sped up his rhythm. “I’m good for now, but I will let you know,” he managed between grunts. His quicker rhythm didn’t much allow for me to continue eating Cathy’s fanny, but I was able to slide two fingers into her and keep her going that way.

Cathy orgasmed and I quickly followed. Derek slowed his pace and then pulled out. I turned and took his very hard penis, covered with my own juices, into my mouth. I gave him the very best blow job I could give, but stopped and had him sit on the sofa. I moved in front of him, slid my hand under his testes and started where I had left off. His penis felt so good and tasted so good in my mouth!

While I was sucking Derek’s penis, Cathy maneuvered herself underneath me. It shocked me when her tongue touched my fanny, I almost choked on Derek! After a moment or two, I was able to get back to my mission – get Derek to cum in my mouth.

I didn’t have to wait too long. Derek’s sperm shot deep into my mouth, hot and salty and tingly! After his second squirt, I started cumming, too, making it a bit difficult to swallow all of Derek’s sperm. What I couldn’t swallow dripped out of my mouth and down Derek’s penis and into my hand cupping his testes. I rubbed it over my breasts as I continued to stroke Derek’s penis with my other hand, keeping the head of his penis in my mouth, sucking out any last drops of his tasty sperm.

The rest of the night was spent with the three of us kissing and cuddling. Derek was able to manage one more erection. We all masturbated together and Derek shot his sperm all over both Cathy and me.

Before I left at the end of that summer, I had had sex with Cathy almost weekly, a few times with Derek, and twice just Derek and me. But those are other stories to tell…