I removed my fingers and eased my engorged cock into her pussy. I began to fuck her slowly and then added first one then two fingers back in her asshole. Linda was on the verge on an uncontrollable orgasm and as she began to thrust and shake, I took advantage of her state and tried to slide my cock from her cunt to her asshole. I managed to get the head outside the sphincter and then Linda panicked. As she bucked and shuddered with an intense orgasm she almost impaled her ass on my cock. Only when she started to come back to earth did she realize that my cock was about to enter her ass.
"Oh my God not in my ass I have never done this", she said in a panic.
"Relax," I told her "I would never hurt you, trust me, you will learn to like this," I reassured her.
"No please no I have never done this and you are too big," she pleaded.
Linda was clearly scared and I didn't want to hurt her or frighten her. I backed off her ass for now thinking that in due time I would conquer her but tonight was the not the night to push it. I moved my cock back into her pussy and resumed fucking her doggy style. Soon I had a smooth rhythm going again and I was sawing in and out of her pussy easily. Fucking her doggy style was the next best thing to fucking her ass. I could still fondle her shapely ass and finger her bung hole. Linda cooed as I fucked her pussy from behind and finger her clit as I plowed into her. Soon I felt my balls tighten just before I blasted another enormous load of cum into her pussy.
My semen was backing up out over my cock and running down over her pussy and inner thighs. My dick softened and I eased it out of her with an audible squishing sound. I collapsed on the bed and Linda lay next to me handling my softening cock. She blew me away when she slid down and took my cock in her mouth.
As she lovingly cleaned my cock with her mouth she kept repeating, "Thank you; oh thank you, thank you."
We then lay still for awhile before Linda spoke again, "I'm sorry about my ass but I have never been ass fucked and I was afraid that your size would really hurt me. I just couldn't go through with it."
"It's okay I understand," I replied and then added, "It was just that your ass looked so hot and you seemed to enjoy my finger in there that I wanted to fuck your ass."
Linda took a deep breath and then said, "I really should get going."
"You are welcome to spend the night if you like," I offered.
"Thanks but Carol will be worried if I don't come home, maybe another time," she replied.
"Sure whatever works for you," I told her.
Linda freshened up, dressed and then left for the night. She kissed me goodnight and told me that she looked forward to working with me and seeing me again. I patted her round shapely ass one more time as she left the apartment. Then I went to bed and fell asleep thinking about Linda's hot curvy ass.
MEETING WITH CAROL
I met with Carol Thursday evening and we arranged for Bonnie to meet us at the house. Carol was a slender woman with beautiful red hair and emerald green eyes. She probably weighed about 115 pounds and stood at 5'6" tall. She was just about flat chested but she was still very shapely and very fit. Her best asset much to my pleasure was her perfectly shaped ass. She wore tight fitting black slacks and it was hard to keep my eyes off her ass.
We met Bonnie at the house and Bonnie stayed with us while Carol toured the house and took measurements. At times when Carol wasn't looking, I fondled Bonnie's round ass and squeezed her firm cheeks. Bonnie stood still for it as she didn't want to draw attention to us. A couple of times I noticed that Carol caught us but she just smiled and went about her work. On a few occasions I noticed Carol checking Bonnie out which led me to believe that Carol might be gay or at least bi-sexual. Then I got to thinking about Carol and Linda living together and I wondered if they were lovers.
Eventually Carol finished her work and announced to Bonnie and I that she was done for now. After scoping out Carol's ass I was horny and I was prepared to put the moves on Bonnie again when Carol spoke.
"Walt what do you say we grab a drink somewhere and I go over my findings and some suggestions with you," Carol offered.
Bonnie looked almost relieved when I accepted Carol's invitation. "Sure that sounds great. Bonnie I'll see you later this week," I said dismissing Bonnie in the process.
Carol and I went to the car and I asked, "Where would you like to go?"
"How about your place, I understand from Linda that you have some great red wine," Carol replied.
"Absolutely," I accepted as things started to look up for the evening.
As we drove over to my apartment Carol told me that she thought Bonnie had a great body. Then she asked me if I thought Bonnie was into girls or at least bi-sexual. I told Carol that I didn't think that Bonnie was into girls at all because of reluctance toward sex at first with me. I explained how Bonnie was willing to fuck me but how I had to bring her along in oral and anal sex.
"So she has really allowed you to fuck her because of the big commission on the house," Carol observed.
"Yes and recently she has accepted her fate in anal sex and oral sex although she still doesn't like it," I replied.
"I bet you could get her to do it with a girl before you close on the house. At this point it seems as if she would do almost anything. I would like to get her in bed," Carol admitted.
"I thought you were checking her out at the house. So are you gay or bi?" I inquired.
"I'm really gay but I also love anal sex and with the right guy I will take a cock in my ass. Linda says that you tried to fuck her in the ass Tuesday night and now that you told me about Bonnie I can see that you are an ass man," she said.
"Yes I am and I love to fuck a shapely ass more than any other form of sex," I admitted.
"Good and maybe I'll let you fuck me in my ass. I love to feel a huge warm load flood my rectum," Carol said in a sultry tone.
All this talk had given me a hard-on and I was thankful that we finally arrived at my apartment. Carol and I went inside and I opened a bottle of wine. We quickly killed the first bottle and I opened a second. Carol then turned our conversation back to sex.
"You know I really do like you and I am willing to let you fuck my ass. But I warn you if you bring that cock anywhere near my mouth or pussy, I'll cut it off," Carol warned me.
"It's women like you that give redheads their reputation. Come on I'll show you the bedroom," I replied and led Carol into the bedroom.
Once in the bedroom Carol quickly stripped off all her clothes and just as I had imagined her ass was incredible. I undressed quickly too and my erect cock stood proud as Carol assessed it. I grabbed the lube from my nightstand and began to put it on my cock. Then she got on the bed on all fours and looking over her shoulder she smiled and spoke softly as she patted her ass.
"You like?" She asked as she stroked her buns.
"You have a beautiful ass," I gasped.
"Put plenty of that stuff in my ass and on your cock. I need to be well greased to take that ass buster of yours," she said sounding a little apprehensive.
I moved toward the bed and climbed on it behind her. I massaged her shapely ass cheeks and molded the firm flesh in my hands. Carol shivered in anticipation and goose bumps appeared on her buttocks and thighs. I squirted the lube directly on her nether hole and pushed it in with my index finger, moving it around until my finger was gliding in and out easily. Before adding a second finger I put more lube in her ass and then inserted my middle finger along with my index finger. She cooed as she accepted the two finger penetration and stimulation. As I fingered her ass with two fingers I slipped my ring finger and little finger in her pussy. I sawed the four fingers in and out of her asshole and pussy until she begged for my cock.
"Stop teasing me and get that big cock in my ass," she gasped.
I put gobs of lube on my cock and then added my saliva making it as slippery as possible. Carol lowered her head to the bed and turned it to one side as I began my journey into her ass. I pushed my hips forward as I held onto her hips and my cock bumped up against her sphincter. Carol gasped and placed her hand on my thigh as if to control the penetration. Another push and my cock head was in her ass.
She was holding her breath as I inched more and more of my cock into her anal passage. I told her to relax and breathe as I slowly fed my cock to her a little at a time. I eased it in, stopped, withdrew a little and then pushed some more in. I took my time and I was careful not to hurt her as I filled her shapely ass with my raging shaft.
"Oh sweet mother of God, I have never been so full. Go easy but put it all in. I want your whole cock in me," she cried out.
I pushed once more and the final inch of my cock disappeared into her asshole. I remained still for a moment and allowed her to adjust to the girth of my cock and then I began to fuck her ever so slowly. She eventually began to move her hips in an attempt to match my thrusts but it was obvious that she had been stretched to new dimensions.
She was gasping and grunting as I began to pummel her ass. Carol's hand was buried in her pussy and she was frigging herself frantically. I picked up the pace and held to Carol's shapely buttocks as our hips slapped noisily together. She was really into it now and the two of us fucked like maniacs.
"Oh yeah that's it, that's the way to fuck my ass. Give it to me, cum in me, cum in my ass," she screamed.
We were both sweating from the physical intensity of our butt fucking. I slammed into her as my cock now moved freely in her ass. I felt my orgasm approaching and as much as I wanted to prolong the ass fucking session, I couldn't. My body stiffened and I plunged my cock all the way into her gorgeous ass. Streams of semen shot into her rectum as I seemed to cum continuously for several minutes.
"Oh good, I feel it. Fill me up, fill up my ass," she cried out and then her own orgasm hit her, "Oh shit, here it is, I'm cumming!"
Her body thrashed around as I held onto her curvy ass cheeks and kept my cock buried in her ass. Her fingers flew over her pussy and clit as my warm seed flooded her anal passage. She then collapsed face down on the bed and my cock slipped from her ass with an audible pop. I knelt over her as my cock dripped the remaining cum on her curvy ass. She wiggled her bottom and squealed in delight.
"I have to admit it I have never been ass fucked like that. You are one hell of a butt fucker," she said and then rolled onto her back and looked at my semi-hard cum dripping cock.
Carol grabbed a bed sheet and wiped my cock clean and dry and then said, "How about another glass of wine and I have a proposition for you."
I poured the wine and listened to Carol's proposition. She made it clear that she wanted to bed Bonnie and she offered up Linda's ass in exchange. Carol told me that she was working on Linda's ass and that she had been breaking her in with anal beads, fingers and a small butt plug. She also told me that Linda fucked her ass with a strap-on dildo just a little smaller than my cock. Carol and I agreed that I would set up Bonnie this Sunday. I would have Bonnie back to my apartment and I gave Carol a key to let herself in the apartment. I would call Carol just before Bonnie and I were ready to fuck. Carol also invited me to her apartment on Friday night and promised me that she, Linda and I would have a great time. All this talk was making me horny and I felt that familiar sensation stirring in my loins again.
"God my body is a little tight and stiff tonight. It must be from all that stretching when I was measuring your house," Carol moaned.
"Would you like a massage?" I offered.
"Sure if you're up for it just keep your hands away from my pussy and my tits," she warned.
Carol's tits really consisted of little bumps but with elongated nipples. "I promise, why don't you just lie face down on the bed and I'll get some oil." I said accepting her threat.
Carol lay face down on my bed as I moved into position to massage her back. She just sighed as I oiled up my hands, straddled her body and went to work on her shoulders. She cooed as I rubbed the tension out of her upper body. I worked my way down from Carol's shoulders to her trap muscles and lower back. I massaged her back just above her buttocks and she continued to coo and moan with pleasure. I bypassed her ass for the moment and went to her calves. I massaged each calf and worked my way up to the back of her thighs. As I massaged the back of her legs and thighs my eyes were fixed on her marvelous ass.
I finally reached the object of my desire and I rubbed plenty of oil onto Carol's buttocks. She lifted her hips slightly as I worked her firm ass cheeks. I pulled her buns apart slightly and stared at the cute little aperture. It was hard to believe that earlier this evening my thick cock had been buried in that tiny hole. I leaned over and ran my tongue over her nether hole causing her to gasp in surprise. I suspected that no one had ever rimmed her before and she moaned again as my tongue probed the target. I traced my finger over the ridges of her now swollen sphincter and watched as it seemed to pulse and throb under its own accord.
I took the bottle of oil and placed it right on her nether hole and let a few drops fall on it. I pushed the oil in her asshole and her hips bucked in response. As my finger entered her channel she gripped it with her anal muscles. I continued to finger fuck her ass adding more oil as needed and eventually adding a second finger. Satisfied that she was well oiled I straddled her hips and guided my slick cock into her ass. My cock head slipped past the oily sphincter and the spongy head disappeared into her ass. Her anal ring snapped closed behind the cock head and I marveled at the sight before me. I only had the head of my cock in her and she lifted her hips and pushed back obviously wanting more.
My cock felt bigger than it ever had as I eased more of it into her anal passage. I watched as it stretched her open and slid easily in her oily hole. I continued my slow penetration until the entire length of my shaft was balls deep in her ass. Carol gasped and grabbed the bed sheets as I hit bottom and then moved her ass in time with my thrusts.
"Oh what a glorious corn hole fuck me, fuck my ass," she rasped.
We fucked slowly as she arched her back and we fitted together perfectly. Her gasps were intermittent and interrupted with cries and sobs of pleasure. Her ass was so snug that I wondered how the semen ever got out of my cock. I fought to hold back my orgasm as long as possible but the undulating walls of her asshole were just too much. I felt the familiar boiling in my balls and I thrust into her as the first blast of cum exploded into her rectum. I barely heard her pleas for me to fill her ass with cum as her contractions milked every drop from my cock. I continued to fuck her slowly and I enjoyed the new feeling of warm semen mixed with the oil surrounding my cock in her sheath.
"I love the feel of your warm cum in my ass," she sighed as my cock remained nestled in her hole.
We remained in the same position for quite awhile. I think we even day dreamed a little and we snapped out of it when my deflated cock slipped from her ass. Carol flattened her body on the bed, turned her head to one side and smiled as she whispered.
"That was so good. I loved it, two loads in one night, incredible. My asshole is full with cum," Carol sighed softly.
I lay next to her for a few minutes and ran my hand over her shapely bottom. Cum oozed from her bung hole and gathered on the cheeks of her ass. I got up and grabbed a towel and then wiped my semen from her ass. Carol took the towel and held it to her ass as she headed for my bathroom. I heard the shower running and then it stopped. Carol emerged from my bathroom and located her clothes to dress and then head home. I watched her dress and then walked her to the door. Carol turned and gave me the European kiss and both cheeks and reminded me about tomorrow night at her place.
"Walt that was a great fuck session and I so look forward to tomorrow night," she exclaimed as she went out the door.
"I'll bring the wine," I said as I patted her shapely ass one more time.
Carol wiggled her ass in reply and walked down the stairway. I closed the door and crashed in my bed. I couldn't believe my good fortune to have met Linda and Carol. Not only did Carol let me fuck her incredible ass but she promised to line Linda up for me to take her anal virginity. As a bonus I still had two more weeks to fuck Bonnie before the closing.
FRIDAY WITH TWO SEXY LADIES
I arrived with a couple bottles of wine at Carol and Linda's place. They greeted with the brush kisses on both cheeks and invited me into their home. The house was very tastefully decorated and showed off Carol talent. They led me into the great room and we opened the wine and sat around chatting for several minutes. Then Carol suggested that we get down to business and go into the bedroom. Once in the bedroom both women dropped their smocks and stood before me in their naked beauty.
I peeled off my clothes as fast as I could as Linda crawled onto their king size bed. Linda lay on her back and opened her legs for me then she stroked her pussy in anticipation.
"I want you to fuck Linda first but don't cum in her pussy yet because I will be eating it later," Carol directed and it was very clear that she would run the show.
I crawled up on the bed and between Linda's legs. She wrapped her shapely legs around my torso and pressed her heels against my buttocks. Linda was still snug when I entered her pussy so I took my time fucking her and let her get used to my cock. Soon my cock was buried in her quim and we both picked up the pace. Once again I made an effort to keep my cock in contact with her clit.
Linda and I were humping each other like mad now as we both raced toward our first orgasm of the night. Linda pulled my head down and kissed me deeply as she threw her hips into me. Linda's body tensed and she groaned into my mouth as her orgasm overtook her. We kept right on fucking and kissing as it seemed that Linda could cum again. I felt my own orgasm approaching as the familiar feeling in my balls was present but I remembered Carol's words and I pulled out of Linda before I came in her pussy. Carol sensed what happened and she replaced me between Linda's legs and sunk a strap-on cock into her lover's cunt. Linda's body leaped out of control and she pounded her pelvis into Carol as she experienced another intense orgasm. Carol must have slipped on the strap-on dildo while I was fucking Linda. It was really hot to watch Carol fuck her lover as it was the first time I had ever seen two girls fuck live.
Carol pulled out of Linda, got between her legs and licked at her snatch. I watched as Carol knelt between her friend's legs and sucked the juices from her pussy. I noticed that Carol's thighs were firm and trim just the way I like them. My eyes then went to her round and firm ass. Since I was still hard I knelt behind Carol and shoved my cock into her ass. She moaned as she felt the intrusion and wiggled her ass in approval. I slowly fucked her from behind and fondled her sensuous ass flesh.
Carol lifted her face off of Linda's pussy long enough to say, "I already lubed up so you can fuck my ass."
Linda then blurted out, "Do it, she loves it in the ass."
Carol grunted as my cock made its way into her tunnel. I stopped with my cock halfway home and allowed her to get used to the thickness. I knew that my cock was the largest one she ever had in her ass and I didn't want her to feel any discomfort. Carol then pushed her ass back toward me and I reciprocated by pushing back and sinking my dick in further into her channel. Soon my entire cock was buried to the hilt and I began fucking her ass slowly and deliberately.